The 10 Best Weekend Getaways in Florida (& Over 60 Activities!)

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Sandy, sweeping beaches. Old, haunted cities with lots of ghost stories. Lots & lots of seafood. Florida is nicknamed the Sunshine State, with an average of 237 sunny days a year. It’s truly the land of a million sandy beaches, theme parks, and a whole lot of things to do. And it’s one of the best places for a mini-vacation with so many truly unique weekend getaways in Florida!

As someone who grew up going to Florida almost every year, I’ve spent many a lazy hour in the Sunshine State traversing beaches, lakes, swamps, and tourist attractions that fall under the branch of a certain kind of Florida-flavored kitsch.

I’ve collected the 10 best weekend getaways in Florida, whether you are looking to sit on the beach, go on adventures, explore its history and hear ghost stories, or see some drag shows and go to the gay beach (yeah, Florida, I said gay).

Private beach in Key West, Florida
Palms swaying in the breeze, sandy beaches, blue water… you’ve arrived!

The 10 Best Weekend Getaways in Florida

Only have a weekend away? There is plenty that can be done in the sunny state of Florida! Below are ten amazing weekend getaways in Florida, whether you are looking for some beach relaxation or some more adventurous offerings.

I’ve included a list of things to do, where to eat and drink, and where to stay for the weekend in each city, so you’ll definitely have a good head start on your planning. So let’s get to it!

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lake eola orlando florida
Outside the theme parks, Orlando is both beautiful and exciting! (Photo Credit)

Orlando, Florida: An Adventure Lover’s Getaway

Orlando, Florida, you may have heard of it. The home of Universal, Disney World, and a thousand tourist traps? But underneath all the glitz and glamour of the major theme parks and miniature golf courses, there’s actually an exciting, cultured city waiting to be explored.

Orlando, originally named the not-so-catchy “Jernigan” (sorry to any Jernigans out there), was once the citrus hub of the world until a deep freeze in the 1800s caused farmers to move their crops farther south. The name “Orlando” has mixed provenance, one account saying it was from a soldier named” Orlando Reeves” who fought in the Second Seminole War against the Seminole Tribe, the original inhabitants of the area.

There’s another theory that it was named after the protagonist Orlando from Shakespeare’s As You Like It, with a man named James Speer proposing in a letter in 1885 that “Orlando was a veritable Forest of Arden, the locale of As You Like It.

However it got its name, the “City Beautiful” has more than 100 lakes, and in 2019 welcomed a record-breaking 75 million visitors. Orlando is one poppin’ place.

What To Do in Orlando

Just because you’re visiting Orlando, doesn’t mean you can’t avoid the typical experiences, and the crowds, if you know where to look. Here are some of the best things to do in Orlando outside the theme parks:

  • Scenic Boat Tour of Winter Park Florida – I have visited Orlando many times and I have to say this is one of the coolest experiences I’ve had here. Located in the stunning (and super swanky) Winter Park neighborhood, the hour-long scenic boat tour takes you across seven connected lakes, through small canals with plenty of wildlife, and past some of the biggest and oldest mansions you’ll ever see – from the water that is. The boat drivers are full of information and terrible puns, so you know you’re in for a good time!
  • Night Glow Paddleboarding – Remember all those lakes I mentioned Orlando having? Well, the best way to experience them is with Night Glow Paddleboarding by Epic Paddle Adventures. Even if you’ve never done standup paddleboarding before, the extremely friendly and fun team will have you up in no time to explore the lake. The best part is, as the sun goes down the paddleboards light up (which you can change the color) and the staff brings a cooler with beer or White Claws and even plays party music (and takes requests!). This is a fabulous way to spend an evening, and the staff truly makes it something to write home about.
  • Morse Museum of American Art – The Morse Museum has one thing on its mind – the world’s most comprehensive collection of works by Louis Comfort Tiffany objects. We all know Tiffany lamps, and there are plenty of unique ones here, but besides lamps there are Art Nouveau vases, jewelry, and even an elaborate chapel interior created for the Chicago World’s Fair in 1893. The mood here is dim and relaxing, and if you have an eye for beauty, you will definitely be at home in this artistic paradise.

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Where to Eat & Drink in Orlando

  • Orlando Milkhouse – I know what you’re thinking – you’re lactose intolerant – lucky for you Milkhouse is really named after the “milk district” in which it’s located. While you can find dairy treats like local ice cream company Kelly’s Homemade Ice Cream here, this is the place to get an incredibly crafted cocktail and some killer food from Cicchetti Kitchen located inside. The menu includes items like handmade Foccacia with ricotta, some killer caramelized Brussel sprouts, as well as their perfectly-cooked Bacaro burger with fonitna cheese, Dijon mustard, Arugula, B+B zucchini pickles, on a Martin’s Potato roll. Grab a craft Foxtail Espresso Martini to get you both alert and relaxed.
  • Ivanhoe Park Brewing Co. – This brewery sits right on Lake Ivanhoe, which was once the home to an early 1900s amusement park called Joyland. Ivanhoe Park Brewing Company pays homage to the area’s fun heritage, with beers like the Joyland IPA to the Toboggan Blonde Ale named after the water slides that used to be on the lake. Not sure what to get? Get a flight to try samples of their beers and book a private tour to hear more about the history and how their beer is made!
  • The Hammered Lamb – As the name suggests, the Hammered Lamb is a great place to drink! Also located across the way from Lake Ivanhoe, this outdoor (and covered) bar and restaurant sits next to the train tracks. And every time a train goes by that means one thing… train shots! Yes, in their quest to get you a little tipsy shots are served every time a train passes. Not to mention their food is quite delicious – hummus of the day with pita and lots of veggies, spicy wings, stacked nachos, and crispy lamb quesadillas. Choo choo!
  • East End Market – East End Market is a culinary food hub, where creative chefs use local ingredients to make one-of-a-kind food experiences. Walking into this place is a bit overwhelming – so many different smells and food options! Winter Park Biscuit Company isn’t just biscuits, but biscuits & gravy, chicken sandwiches, and burgers… And it’s all vegan! Deceptively so. Their Crispy Chik sandwich was the juiciest vegan chicken sandwich I’d ever tasted. Besides other savory foods like Domu where you can get some seriously savory ramen, check out Gideon’s Bakehouse with their Gothic, witchy aesthetic and cookies that are nearly a half-pound each!
swimming pool at Caribe Royale Orlando florida
The swimming pool at Caribe Royale Orlando is truly an oasis. This could be an entire vacation!

Where to Stay in Orlando

Orlando has plenty of beautiful places to stay, whether you want more of a resort feel or your own private getaway. Here are some of our favorites:

  • The Caribe Royale Orlando is located on World Center Drive, a stone’s throw away Disney from if you plan on visiting on one of your days and they even have their own Disney transportation. The hotel itself is recently renovated with large, spacious and modern rooms, and plenty of dining options on-site. The crown jewel of the hotel is its large pool area, which includes waterfalls and a waterslide. While this hotel is not exactly a budget hotel, it’s worth the splurge for the amenities and convenient location.
  • This beautiful rental with a heated pool has a bright, spacious bedroom and bikes you can borrow to explore the super cute Winter Park neighborhood and is just blocks away from Morse Museum of American Art.
  • For an even more budgets friendly option, check out this colorful mid-century modern condo also located in Winter Park, and just a 15-minute walk from the Scenic Boat Tour of Winter Park Florida. You really can have it all!

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New Smyrna Beach: An Art Lover’s Getaway

New Smyrna Beach has a whole lot of history – it is the third oldest city in Florida behind St. Augustine and Pensacola. Scottish physician Dr. Andrew Turnbull established New Smyrna in 1768, though the land was already inhabited by the Seminole Tribe. Turnbull’s wife was from the Ottoman (Turkey today) city of Smyrna, from which he decided to name the city New Smyrna.

Today new Smyrna is known as an artists’ hub, home to the Atlantic Center for the Arts as well as The Hub on Canal, a community-based arts center where local artists teach and sell their works. Here you can find ocean-inspired artwork (or not!), in all kinds of mediums by people who flock to this town for creative inspiration.

New Smyrna Beach is also known for its incredible surfing, ranked by Surfer Magazine as the number 5 best surf town. With waves almost every week of the year, New Smyrna is a hot spot for surfers and surf culture, even though New Smyrna is known as the “shark capital of the world” due to the nearby inlet. So maybe stick more to art, and leave the surfing to the pros!

What To Do in New Smyrna Beach

There is plenty of art, history, and lots of local charm to discover in New Smyrna Beach! A few of the best activities are:

  • Marine Discovery Center Boat Tour – Take a 2-hour Dolphin Discovery boat tour on North America’s most biologically diverse estuary, with over 4000 species that call this area home. You’ll see great egrets nesting, different species of mangrove trees, and of course, plenty of dolphins. I’ve never seen so many dolphins at one time as I did on this cruise, them jumping and playing both by the boat and in the distance. If you need your adorable dolphin fix, this may be the best place to see them!
  • Smyrna Dunes Park– This 184-acre inlet park provides two miles of boardwalks where you can see gopher tortoises nesting within the lush dune foliage. The boardwalk also has plenty of overlooks of the gorgeous Atlantic Ocean, Indian River, and Ponce de Leon Inlet. This is a great place for a stroll, and to head to the beach to walk along the jetty and gander at the Ponce de Leon lighthouse across the inlet.
  • Explore the Canal Street Historic District – What used to be a literal canal 250 years ago, which was used to deliver goods like can sugar and indigo from the mainland to the Indian River, Canal street today is still the cultural hub of commerce and art. Here you can find shops like The Gallery which sells gourmet balsamic vinegar (I recommend the pomegranate kind!), as well as The Hub on Canal, which is a community-supported art space where local artists sell their wares. They do monthly events as well like the Classic Cruise Car Show, art strolls, and gallery walks. There is always something going on!
  • Check out the History Museum and Old Fort Park – New Smyrna is home to lots of culture and history, since it’s the third oldest city in the state! Stop by the New Smyrna Museum of History first to learn about the original Native Americans, the Spanish’s arrival, how indigo dye became a cash crop for the city, and its totally tubular surfing scene. Afterward, head across the street from the museum is Old Fort Park, which is open and free for you to walk across the mysterious ruins. No one knows what this sprawling foundation was originally holding up: was it a colonial church? Dr. Turnbull’s mansion? A site for constructing ships or the original Castillo de San Marcos? No one knows!
  • Walk around the Old Sugar Mills Ruins – Three miles away from the museum and Old Fort Park are the Old Sugar Mills Ruins, which was originally the Cruger-de Peyster sugar mill. In the 1830s, the US tried to forcibly push the Seminole Tribe off their own land, so they burnt down the Spanish colonizer’s mill in retaliation. Today this free park is hidden amongst palm trees containing high-sweeping arches and rusted metal vats, and is a great place to learn about the conflict of the original inhabitants of the land and those who intruded. Be aware the park entrance is not well marked – go to 600 Mission Drive, New Smyrna Beach, FL and enter the small road that goes into the forest.

Where to Eat & Drink in New Smyrna Beach

A treehouse, a fairy garden, and a marina… all with delicious food! New Smyrna has some excellent food in some unexpected locations, let’s dig in!

  • Norwood’s Eastery & Bar Treehouse – Norwood’s is the kind of place that makes you feel like a kid again, because you can actually eat dinner in a giant treehouse with twinkling lights! Sit out on the second-story patio nestled amongst the trees and eat super fresh seafood (this is Florida after all), like coconut shrimp as an appetizer and the Admiral’s Platter for dinner, with a 50oz lobster tail, grilled Mahi, and broiled sea scallops and shrimp. Order an All Night Long to drink, with bourbon, orange, lemon, bitters, and pinot noir float. You won’t be leaving hungry here!
  • Third Wave Cafe and Wine Bar – Eat outside at the Third Wave Cafe and Wine Bar is like stepping into a garden paradise, with palms, string lights, and plenty of evergreen plants and pergolas to make you feel cozy and magical. To start, order the Wagyu Short Rib Hummus, with hummus they make from scratch, over-roasted boneless Wagyu short rib, toasted Pita, Za’atar harmony herbs, and EVOO, or the Shrimp Gambas (Spanish style shrimp) with Creole butter sauteed, wild-caught American shrimp, garlic, chilies, Calabrian oil, and crisp baguette. For a fresher-than-fresh entree, get the Smart Catch, a Chefs catch with blackened honey pecan-crusted, shrimp, whiskey butter cream sauce, chef’s vegetable, and Yukon mash potatoes. Everything here is exquisite in flavor and preparation!
  • Outriggers Tiki Bar and Grille – For perhaps the best place to get brunch in New Smyrna, check out the Outriggers Tiki Bar and Grille. Situated right along the marina, watch boats go by as you dig into some Chicken & Waffles with cinnamon butter, sausage gravy, and bacon amaretto sauce, or the Crab & Lobster Cake Sandwich, with Florida spiny lobster, crispy Panko fried lump crab, chipotle lime sauce on a brioche bun.
Smyrna Dunes Park beach and jetty
You can never go wrong with being close to the ocean.

Where to stay in New Smyrna Beach

When at the beach, you want to stay near the beach! Here are some great beach options on a budget:

  • This super beachy cottage is literally just steps away from the beach and priced just right! With a kitchenette and single bedroom and bathroom, you’ll have everything you need to explore the super adorable New Smyrna and have sand between your toes in no time!
  • The Sea Vista Motel has a vintage charm and is right on the water, so you can get to the beach in a jiffy! There’s also a pool and a connected Tiki bar, so it’s a great place to grab a drink and watch the waves roll.

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driftwood trees at boneyard beach in jacksonville florida-Blog Photo-2
The massive driftwood trees at Boneyard Beach are otherworldly!

Jacksonville: A Nature Lover’s Getaway

Jacksonville is the largest city by landmass in the continental US, coming in at a whopping 840 square miles! With so much area you can bet there are plenty of adventures to be had – and it’s one of the best weekend getaways in Florida especially in terms of getting in touch with nature.

With such a large landmass it also makes sense they have the largest urban park system in the country, which is four times the size of Manhattan at 80,000 acres. You’ve got a lot of exploring to do!

Basically, if you want to get outside and explore the best of Florida’s flora and fauna, “Jax” is the place to visit, with an average of 270 sunny days a year and 22 miles of beaches.

What To Do in Jacksonville

Put on your bathing suit, slather up in sunscreen, and get ready to do some exploring. We have yoga, kayaking, and a “boneyard” beach!

  • Sunrise Yoga with MBody Yoga I know, I know, waking up before the sunrise may not sound like the most relaxing activity, but it’s a great way to begin your morning on a weekend getaway in Florida. As you stretch with guidance from your instructor on Neptune Beach, your whole body will awaken as the sun slowly rises from behind the Atlantic Ocean. Really nothing is as serene as a beach sunrise, the warm salty air entering your lungs as you feel your muscles release.
  • Boneyard Beach – Located along a 3-mile stretch of the Nassau Sound is Boneyard Beach at Big Talbot Island State Park. These “bones” aren’t really bones at all – but massive driftwood trees that cover the beach like an elephant graveyard. The sun has bleached these huge “bones” while the wind and sand has made them smooth, and you can walk along these gnarly skeletons and even climb them. These dead trees protect from further erosion of the flora behind the beach and make a great place for a somewhat morbid and whimsical walk.
  • Try Stand Up Paddleboarding in the ocean – Even if you have never SUPed before, Jacksonville Surf and Paddle will take good care of you as you put on a wetsuit, paddle past the waves, and try your hand on standing and paddling on your SUP! Paddling on the ocean is both exciting and serene, getting to go farther offshore than you normally would swimming. Even if you fall, you’ll splash gently into the ocean and climb back on. Their 90-minute beginner classes are the perfect spot to get your feet wet (literally) and you may find you’re hooked on paddleboarding before you know it!
  • Take an eco kayaking tour – If you want to learn more about Jacksonville’s expansive natural areas, take an eco-tour with Kayak Amelia like their 3-hour Salt Marsh Eco Tour from Ft. George Boat Ramp. Paddle through the Fort George/Simpson Creek estuary through the salt marshes while you learn about the Timucua Tribe who were indigenous to this land, see spitting oysters among the Spartina grass (really!) and plenty of birds like osprey, and even stop on a sandbar for homemade cookies (that’s what keeps coming back, they say!). Our tour guide that day was a former teacher named Buddy, and you can tell Kayak Amelia has a true love of teaching and the environment.
North Beach Fish Camp jacksonville florida fish plate
The Roast Cod Filet drenched in butter from North Beach Fish Camp.

Where to Eat & Drink in Jacksonville

From the ocean to your mouth, Jacksonville has plenty of fresh fish eats with a whole lot of flavor! The following restaurants are located in Neptune Beach, a great place to have a bite then walk along the beach.

  • North Beach Fish Camp – North Beach Fish Camp is a nautical-themed restaurant, with, as you guessed, fish! For starters, you can’t go wrong with the Crispy Calamari with Pecorino cheese & spicy tomato sauce or, if you’re feeling adventurous, the Fried Gator Tail with Cowgill’s Datil pepper aioli (hey, this is Florida after all). The Roast Cod Filet with Brown Butter, Garlic & Lemon, Parsley Potatoes and Seasonal Vegetables is a perfect lighter option, too!
  • Southern Grounds – For a morning pick-me-up (after yoga, no less), head to Southern Grounds for some delicious and strong coffee and some pancakes, a bagel sandwich, or even loaded avocado toast. This place is busy in the morning, so grab some eats and a table on the patio outside.
  • Sliders Oyster Bar – This pink flamingo-themed, ultra-retro and modern chic beachside joint may be the best place to get Oysters in Jacksonville in the coolest setting. Grab a table or picnic table with friends on the patio and get ready to dig into some fresh seafood delivered daily! The main event of course are the Oysters steamed or raw, and specialty oysters like the Rockefeller (spinach, parmesan, provolone, and breadcrumbs) and casino (with bacon and a three-cheese mix), among others. For something not oysters, try their shrimp nachos with pico and queso, and get the Hobbs Rum Punch with two different kinds of rum with banana, orange, pineapple, and grenadine!

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Where to Stay in Jacksonville

Jacksonville has 22 miles of beaches, so it’s definitely the spot to book a place on the water! A couple of options are:

  • While the One Ocean Resort & Spa is definietly on the pricier side, if you’re looking for a place in the heart of Neptune Beach and want some swanky amenities like a spa, One Ocean Resort & Spa is the place to treat yourself. Located right on the beach and steps away from MBody Yoga and the restaurants mentioned above, you can chill out in their pool and take in all the beachy, calming ambiance of this gorgeous resort.
  • This beachside apartment is only a block away from Jackson Beach and a short walk to the Jackson Beach Pier and plenty of local beach bars. This one-bedroom ground-floor apartment has an outdoor patio for lounging, a kitchenette, and perhaps the perfect location!
sanibel lighthouse sanibel island florida
The lighthouse is the iconic image of Sanibel! (Photo Credit)

Sanibel Island: A Relaxation Lover’s Getaway

Sanibel Island is one of my favorite places in the world. I have been coming here since I was a kid with my extended family, and I never tired of the miles of shelly beaches, the quaint locally owned businesses, and the Bubble Bread. Mmmmm. More on that in a minute.

Sanibel Island, and the connected Captiva Island, is located off the coast of Fort Meyers on the Gulf of Mexico, and this little island is situated in such a way (East to West) that it’s the prime spot for shelling. Some of the rarest shells in the world are found here, like the famous Junonia, and there is even a name for people bending over to pick up shells: the “Sanibel Stoop”.

Sanibel Island feels like a true place to relax – no big chain stores or restaurants but rather local shops, shelling cruises, and a whole lot of “Sanibel Stooping”.

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shells on sanibel island florida
Shelling and doing the “Sanibel Stoop” is the thing to do on these shelly, gorgeous beaches. (Photo Credit)

Things to do on Sanibel Island

Sanibel Island is the perfect place to do some activities – or not! No one will blame you for just shelling all day on the beach or watching one of their famous sunsets. But if you do want to get out and about, here are some of my favorite activities:

  • Take a Shelling Cruise – If Sanibel Island isn’t quiet and remote enough for you, book a Half Day Cruise to Southern Cayo Costa. This trip is approximately 3 hours and leaves from Captiva Island and takes you to Cayo Costa State Park, which is just north of Captiva. On this section of the island, there are no amenities – all you get is the beach, sand, and plenty of shells! Here you’ll find all kinds of shells like tulips, olives, scallops, and maybe if you’re really lucky, the elusive Junonia. Just remember not to collect any shells with living creatures in them – that’s their home!
  • Enjoy the wildlife at a Wildlife Refuge – The J.N. “Ding” Darling National Wildlife Refuge is part of the world’s largest undeveloped mangrove population and is famous for its spectacular migratory birds that come here. Take a drive through this 6400-acre preserve, with plenty of places to park and trails to explore. You can even climb many towers to stand and bird from!
  • Bike around the Island – With over 25 miles of biking trails, the best way to explore Sanibel Island is by bike. The island is only about 12 miles across and 3 wide, so it’s easy to see the beaches, wildlife, and the palms swaying above as you traverse it. There are plenty of places to rent bikes, and most VRBOs and hotels will have ones you can borrow. Stop by Periwinkle Place as you bike too, to find all kinds of fun shops to explore.
orange crunch cake from the bubble room sanibel isalnd
The Orange Crunch Cake from the Bubble Room is highly addictive. It’s hard to only eat it once on your trip! (Photo Credit: Dad)

Where to Eat & Drink on Sanibel Island

Since Sanibel Island doesn’t have any chain restaurants (okay, okay, they have one Dairy Queen), you’ll find plenty of local places, some of which are even world-famous!

  • The Bubble Room – You can’t mention Sanibel Island without asking if they’ve been to the Bubble Room (or maybe that’s just me). The Bubble Room, actually located on Captiva Island, is an ultra-themed restaurant filled with kitsch and vintage memorabilia from the 30s and 40s. The walls are lined with old movie stills, vintage toys are in every nook and cranny, and there are even toy trains that run along the ceiling from room to room. The real star of the Bubble Room is its Bubble Bread, made with several kinds of cheese on Italian bread which comes with every entree (the recipe is closely guarded of course). Their other star is their huge slices of cake, like their Orange Crunch cake, a yellow cake layered with almond brown sugar, and covered in orange cream cheese icing. You can even come just for dessert!
  • The Island Cow – This casual restaurant touts “udderly great food”, which is true! This may be the best place in all of Sanibel to get brunch, and they serve your table a basket of complimentary homemade muffins as starters, which is something I feel very passionate about. For breakfast, try their Hash Brown Benedict with 2 poached eggs and Canadian bacon on waffled hash brown. What?! For lunch, have the Sesame Tuna Steak Salad – fresh pan-seared yellowfin tuna with sesame seeds and a honey ginger glaze on a fresh garden salad with our homemade citrus vinaigrette.
  • The Lighthouse Cafe – The Lighthouse Cafe’s sign says “the world’s best breakfast”, and I have to say, their french toast is something dreams are made of. While there is nothing revolutionary about their flavors or dishes, they are classic breakfast foods cooked perfectly, where waitresses putter around with pots of coffee ready to give you a refill. Get here early and enjoy some damn good breakfast.
sanibel island sunset florida
There is something so magical about a Sanibel Island sunset, with the promise of another day of shelling… (Photo Credit)

Where to Stay on Sanibel Island

Staying on Sanibel can get pricey, it is a small island and paradise after all, but here are some places for a weekend getaway in Florida on a budget:

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city shot of tampa flordia
Tampa is a great city to explore by the water! (Photo Credit: Visit Tampa Bay)

Tampa: A City Lover’s Getaway

Spanish colonizer Ponce de León first “discovered” Florida in 1513, though in actuality the extinct Pohoy and Tocobaga Native American Tribes lived here long before. The myth persists to this day that de León came to America to find the “Fountain of Youth”, though there is no hard evidence that this is true, and it is more likely he was only looking for gold and land to steal.

After that, the area remained more or less untouched until it became part of the US in 1845, and in 1884 a man named Henry B. Plant built a railroad down to Tampa with lavish hotels along the way.

Since then, Tampa has grown into an up-scale, busy city with no shortage of entertainment, aided by the cigar industry that Vicente Martinez Ybor established there in the 1880s.

Things to do in Tampa

Manatees, magnates, and ghosts, oh my! Tampa really has a generous mix of old-world Florida and natural habitats for wildlife, so you can get a great mix here.

  • Visit the Estate of a Railroad Tycoon Even by the late 1800s, Florida was still largely underdeveloped, so a man named Henry B. Plant connected Tampa to the rest of Florida by railroad and built hotels along the tracks. The only hotel of his that is still fully standing is now the Henry B. Plant Museum, located in downtown Tampa. The beautiful property reflects the height of the Gilded Age in America – with its Moorish and Victorian architecture and its silver minarets that have become an architectural icon of Tampa. Inside, you can see everything from imported Japanese vases made in the 1800s to gold plated French chairs – this museum is a dream for anyone who appreciates fine decoration and furniture.
  • Meet the Ghosts of Ybor City Meet two types of spirits on this Haunted Ybor Pub Walking Tour as you explore four of the spookiest pubs in downtown Tampa. While you enjoy drinks, the costumed tour guide will tell the haunted history of each place. The guides are dressed in corsets and tunics and look like they just stepped off the set of a pirate movie (minus the swords, of course). Haunted pub tours are few and far in between, so make sure you visit this one while you’re here, and be sure to check out some of the last remaining cigar factory while you’re here!
  • Spot The Uncommon Manatee – Centuries ago, when pirates and European explorers were out on the sea for months, they would often come home claiming they had seen beautiful women in the water. Today, it’s thought that these sailors were seeing manatees from a great distance. In the 1980s, a power station in Tampa was shut down and that same year, people noticed manatees coming in great numbers, and the federally protected Manatee sanctuary Tampa Electric’s Manatee Viewing Center was born. Here you can watch manatees hug and play with each other in the water and learn what the sanctuary is doing to help their conservation.

Where to Eat & Drink in Tampa

Since Florida is so close to Cuba (just about 90-100 miles at the southernmost point of Florida) there is plenty of Cuban food to try, along with food prepared by the Native American population (mainly Seminole & Miccosukee Tribes). Pair that with a world-renowned steak house and you have one of the best weekend getaways in Florida.

  • Mandy’s To Go – This spot is one amazing piece of Cuba in Tampa. Mandy’s has a very home-cooked feel to it – the employees are really personable too – and all the portions are super big. Their Cuban sandwiches are all outstanding (the bread is soooo fluffy) but my favorite sandwich is the Media Noche, which is a pressed sandwich with mustard, ham, pickles, & pork. I have no idea what their secret is, but I’m obsessed. As the name suggests, the food is to go only, so pick up sandwiches and then go to the beach for a fun picnic!
  • Ulele – At Ulele (You-lay-lee), you can find food that is inspired by the Native Tribes of Florida. Ulele is located on the Hillsborough River, and the Tampa Riverwalk next to it is colorfully lit up at night. Most of the ingredients are sourced from around the Bay area, and the others are from small American farmers that don’t use hormones. They also sell craft beer made on-site, if you’re into that kind of thing. The okra fries are wonderfully crunchy, with a hint of lime & salt. My favorite meal is the Gouda grouper – I never would think to pair a deliciously seasoned grouper filet with a Gouda ale béchamel but hey, I’m not a chef for a reason. Since Ulele is on the Riverwalk, it can get pretty popular on the weekends, so make a reservation.
  • Bern’s Steakhouse – This is a restaurant you’ll see on every ‘Best of Tampa’ list or travel guide, but it’s there for a reason – Bern’s Steakhouse is fantastic and has been around in Tampa since 1956. Walking into this massive restaurant feels like walking into a Victorian castle – the walls are a deep red, with a stone facade on the bottom half, and old pictures in elaborate, silver frames hang on the walls. Their meat is perfection, like the A5 Japanese Wagyu tenderloin, which is one of the highest quality beefs on the market, but any steak you order will be cooked expertly to your liking. When you’re ready for dessert, they are served in an entirely different room upstairs, and I recommend the super-rich and fudgy 12-layer chocolate cake slice. Make sure to make a reservation online or over the phone well in advance, and their dress code is business casual to semi-formal.

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tampa riverwalk florida getaways
Walking down the Tampa Riverwalk is a great way to end any day in Tampa! (Photo Credit: Visit Tampa Bay)

Where to Stay in Tampa

Tamps is a great place to stay, especially if you stay near Ybor City or the Downtown area by the Tampa Riverwalk. Here are some places in those areas:

  • This Secluded Retreat is in the heart of the historic Ybor city and close to downtown, making it the perfect spot to stay during your trip. It’s spacious and clean with two bedrooms, so bring some friends along!
  • This super cute hotel room at the Florida Palace Hotel is right in the heart of Downtown and will give you some serious Beauty & the Beast vibes. It’s also right next to the Tampa Riverwalk, so you’ll have entertainment available whenever you like!
ocean drive miami florida-Blog Photo-2
Miami is home to beautiful beaches and beautiful Art Deco architecture. (Photo Credit)

Miami: A Beauty Lover’s Getaway

Miami is known for lots of things, like the trendy and glitzy South Beach, the world’s largest collection of stylish Art Deco buildings, and maybe most iconically, where the Golden Girls live.

Miami was originally inhabited by the Tequesta Tribe, until the Spanish claimed Florida for themselves in the 1500s, and was named after the Miami River – “Miami” meaning “big water” in the Tequesta/Miyami language. Miami came to be known as the “Magic City” in modern times because it went from nowheresville in the early 1900s until the Florida land boom of the 1920s made it seem to spring up by “magic”.

Today you can still see relics of the boom with the fabulous 1920s-30s Art Deco architecture, and check out historic neighborhoods like Little Havana, Miami’s vibrant Cuban heart where you can eat at some of the best restaurants and puff on a cigar.

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vizcaya in miami florida
The Vizcaya Museum & Gardens is like stepping into Europe! (Photo Credit)

Things to do in Miami

Though Miami is Florida’s second-most populous city after Jacksonville, it isn’t very big – at only 36 square miles it’s easy to take in the best of Miami in just a weekend. Some of the best things to get a taste of Miami are:

  • Take the Miami South Beach Art Deco Walking Tour – As previously mentioned, Miami is home to the largest collection of Art Deco buildings in the world, which is a style from the 1920s and 30s characterized by strong colors and boldly delineated geometric shapes. In other words, it’s what makes Miami look like Miami! On this two-hour tour, you’ll learn about mob life and Hollywood glamour through the lens of architecture, and even see Versace’s over-the-top mansion.
  • Explore the Vizcaya Museum & Gardens – Built by agricultural equipment builder James Deering between 1914 and 1922, this sweeping estate exemplified the European villa style with over 10 acres of formal European-inspired gardens with lilies in a sweeping pool, orchids, hidden grottos and mangroves and much more. Inside the Mediterranean-style home you’ll find antique Italian objects and plenty of ornate, gilded furnishings truly giving Vizcaya the name “Miami’s home”.
  • Do the Little Havana Food and Walking Tour in Miami – A great way to get a taste (literally) of Miami is to take a food and walking tour of Little Havana. Little Havana is an integral part of the heartbeat of Miami, since the city is home to many Cuban immigrants and the population is 70% Hispanic. On this 2.5-hour tour you will get to sample the local cuisine, like guava pastries, chicken plantain cups, and flan ice cream, and meet local artists, watch skilled Cuban cigar rollers and listen to traditional Cuban music.
terras rooftop patio with tacos and beer miami florida
Terras has a tropically overgrown rooftop restaurant & bar, perfect for great food and great sites! (Photo Credit: @terrasmiami)

Where to Eat & Drink in Miami

If you’re visiting Miami, you can bet your buns you’re going to have some good Cuban food, the flavors of which are going to dance over your tongue like a mambo. Here are some places to get great eats:

  • El Rey de las Fritas – A Cuban Frita is a Cuban hamburger that was invented in Havana sometime in the 1930s. Their Fritas are made with a ground beef patty with sautéed onions, topped with crispy shoestring fries, while sitting on a fluffy Cuban roll, and a “secret” built into the patty. This will satiate our fast food cravings – but fast food that is actually good and homemade – so pop in this adorable diner and try a taste of Cuba.
  • Terras – Terras has the distinction of being the only rooftop bar and restaurant in Little Havana, and it’s like stepping into a lush jungle that also happens to have views of the Miami skyline. The best word to describe this place is chic. Here you can get tapas with locally sourced ingredients, like the sweet corn “cachapa” pancakes, pollo tacos, and shrimp seviche, and cocktails like the Guavaloma made with Rosaluna mezcal, guava grapefruit syrup, grapefruit soda, and grapefruit sugar.
  • Monte’s Coconut Grove – Located on the marina, Monte’s Coconut Grove is the place to get fresh seafood in a tropical setting. Step under the thatched rooves of this tiki hut setting and order some Conch Fritters that are fried in spicy batter with cocktail & tartar to start along with some Gulf Oysters. For your entree, you can’t beat good old-fashioned fish and chips, or step it up with the Mahi Sandwich. But honestly of you just ate oysters and drank mango margaritas I wouldn’t blame you either.
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Even the lifeguard shacks in Miami are beautiful! (Photo Credit)

Where to Stay in Miami

Whether you want to be close to little Havana under a mango tree, or right on the beach, Miami has options!

  • This charming garden cottage is super cozy, cute, and magical – your very own private plant paradise. Located right by the city center and Little Havana, you can explore the city and then come back to your own secluded haven, eating outside under a mango tree. The inside is just as cute and colorful with a queen-sized bed and a kitchen.
  • This super modern and stylish one-bedroom apartment is located just a 5 to 10-minute walk to all the best of South Beach. Besides a kitchen to cook in, this building also has its own shady pool, certain to keep you cool on hot afternoons!
  • For an awesome budget option, this condo in an actual Art Deco building may be small but you have the beach at your fingertips! And you can’t beat staying in a piece of history.

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A large rainbow flag flies at the 12th Street Beach, South Beach, Miami
Yes, we say gay in Florida! (Photo Credit)

Fort Lauderdale: A Gay Getaway

Though only about 45 minutes away from Miami, Fort Lauderdale is a super hot spot for LGBTQ+ travelers. Even their current mayor is gay! If you want some good old-fashioned gay fun (yes, we say gay here!) Fort Lauderdale is the place to see excellent drag, check out the gay bars, and of course, sandy (gay) beaches.

The City of Fort Lauderdale is named for the second Seminole fort built to fight the Seminole Tribe in 1838, as European colonizers stole their land and drove them out. The city today is nicknamed “The Venice of America”, due to the 300 miles of canals and channels which are called the Intercostal Waterway.

So grab your cutest outfit, your dancing shoes (or flip flops), and let’s explore Fort Lauderdale.

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Sebastian Street Beach is the gayest beach in Florida, maybe the world! (Photo Credit)

Things to do in Fort Lauderdale

Fort Lauderdale is all about fun, drinks, and beach time! If this sounds like spring break, you’re not wrong, as Fort Lauderdale was where spring break originated in 1938! Talk about a party town.

  • Visit the Gay Beach – Fort Lauderdale is know, as so much of Flordia really, for their beaches, and they have 23 miles of beaches crammed into 36 square miles of city. That’s a lot of beaches! Sebastian Street Beach is known as the gay beach, and is a great place to people watch and meet other couples both locally and on vacation.
  • Check out some gay history – Fort Lauderdale is home to not one, but two gay museums. The first is the Stonewall Museum & Archives, where you can learn about the Stonewall Riots that became the catalyst for the gay liberation movement. Here you can see photographs, clippings, and memorabilia from the riotd as well as modern gay ephemera. The other is the World AIDS Museum and Educaiton Center, where you can learn the sad story of the AIDS epidemic, the pitiful government response, and the hope to stamp out HIV/AIDS once and for all in the future.
  • Check out the canals and channels on a sightseeing cruise – If you’re visiting Fort Lauderdale for the first time, you may be curious about the “Venice of America”. The city has 165 miles of navigable waterways, and looking at photos of the city it does all seem to be floating on water! Luckily you can take a 90-Minute Narrated Sightseeing Cruise, where you’ll cruise along the New River past Millionaire’s Row and learn about the area.

Where to Eat & Drink in Fort Lauderdale

In Fort Lauderdale, you can keep it gay all through dinner, and for drinks afterward! Not only that, you can have dinner and a drag show – it’s true!

  • Lips Drag Queen Show Palace, Restaurant & Bar – Dinner theatre can only be better when drag queens are involved, and Lips just does that! Wednesday through Sunday they do a different show with a different menu each day, like “Glitz & Glam” on Friday and Sunday, “Dragalicious Brunch” on Sunday with bottomless mimosas, and even a “Taboo 21+” show late Saturday nights. Talk about dinner and a show, hunty!
  • Rosie’s Bar and Grille – For a big gay time in a casual atmosphere, check out Rosie’s Bar and Grille. Sit on their outdoor patio surrounded by lush foliage under colorful umbrellas and rainbow lanterns, sipping on fruity drinks like their Watermellon Basil Martini, an Orange Bubble Crush, or a Blue Wave. Foodwise, they have awesome burgers, sandwiches, nachos, and much more!
  • Check out the Wilton Manors Gay Bars – Wilton Manors is the main gayborhood of Fort Lauderdale, though technically it’s actually its own city! Along Wilton Drive, the main gay thoroughfare, you’ll find bars like Infinity Lounge for an after-work drink, Hunters for dancing, and The Pub for amazing drag shows. This strip is easily walkable, and just make sure you’re respectful if you’re not a queer person entering a queer space!
A private pool on my weekend getaway? Don’t mind if I do! (Photo Credit)

Where to Stay in Fort Lauderdale

Staying in Fort Lauderdale for the weekend has options – whether you need the beach within walking distance, or the bars of Wilton Manors!

  • This central Wilton Manors studio apartment is right in the heart of Wilton Manors, making bar hopping/crawling easy and safe! The apartment is modern and clean, and the best part is your own private pool in the backyard surrounded by palm trees and flowers.
  • For that beach life, check out this super chic apartment that is right on the scenic Intercoastal Waterway. When you’re not watching the boats roll by from your spacious apartment, you can cool off in the pool or walk a block to Fort Lauderdale beach!

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38 Enchanting Things to Do in Savannah, Georgia

st pete beach florida
St. Pete Beach is the best beach in America you say? Don’t mind if I do… (Photo Credit)

St. Petersburg: A Beach Lover’s Getaway

St. Petersburg — or St. Pete, for short — has a beach for every occasion. With top-rated beaches stretching 35 miles along the Gulf of Mexico, you can visit a different world-class beach every day. With lively urban beaches — and the open-air bars, volleyball games, and vibrant energy that come with — quiet, undeveloped island beaches, and everything in between, you’ll want to pack plenty of sunscreen (and a boogie board) for your weekend in St. Pete. 

That’s not to say there isn’t plenty more to do if you need a break from the sun (St. Pete averages 360 days of sun per year!). Cultural attractions — like the Salvador Dali Museum and the Chihuly Collection — and an exciting food scene can punctuate your fun in the sun.

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All this nature is right at your fingertips in Fort de Soto Park! (Photo Credit)

Things to Do in St. Petersburg

Sandals? Check. Sunblock? Check. Let’s look at the best beaches and natural activities in St. Pete!

  • Hit One of America’s Favorite Beaches – Rated the #1 beach in the US by Trip Advisor in 2021, St. Pete Beach is everything a beach should be. White, sugar sand; unbelievable sunsets; clear, emerald water, and — of course — beach bars. Spend the day soaking up the sun, splashing in the surf, and marveling at the undeniable beauty of this Gulf Coast beach. And at the end of the day (heck, whenever you want), head to one or two of the open-air beach bars — Jimmy B’s has live music and a sprawling, beachside patio.
  • Enjoy Beaches and History at Fort De Soto Park and Egmont Key Fort De Soto Park encompasses five islands and lots of shoreline in the Gulf and Tampa Bay. You can hike, bike, relax on the beaches, and even explore the historic fort — completed in 1900. You can even take the ferry over to Egmont Key, a secluded island where you can hike, swim, or snorkel among old fort ruins. Look at you, Indiana Jones!
  • Explore an Undeveloped Island – If you plan for a day trip, Caladesi Island State Park (which requires a ferry ride) is a quiet island, perfect for a relaxing day spent swimming or bird-watching. If you want to escape the beach for a bit, there’s a wonderful nature trail that will take you through the heart of the island to historic ruins. This trail goes to the Scharrer Homestead ruins, which is what remains of a late 1800s house, where Henry Scharrer, a Swedish immigrant, used to live. You can also rent a kayak on the island and kayak one of the paddling trails through the shallow, clear water.
  • See Florida Wildlife by Paddleboard – What better way to experience Florida’s wildlife than by a peaceful paddleboard tour? You don’t have to be a pro to take this tour — in fact, newbies are welcome. After learning the basics of how to navigate your board, you’ll head out on the bayou in search of manatees, dolphins, and a diverse array of birds. 
doc crow's st petersberg florida
Talk about lunch with a view, Doc Ford’s Run Bar and Grille is its own paradise! (Photo Credit: @docfords)

Where to Eat & Drink in St. Petersburg

St. Pete has so much to offer in the food and drink scene, from the typical fresh seafood, to custom-made cocktails with a rotating menu. Here are some of the best places to eat and drink in St. Pete:

  • Doc Ford’s Rum Bar and Grille – Located on the St. Pete Pier, Doc Ford’s Rum Bar and Grille sits right on the water giving you excellent views of Tampa Bay. Get the Macadamia Nut Crusted Grouper, which is served atop an exotic mix of quinoa, jasmine rice, arugula, red peppers and yellow squash then complimented with a “Toasted Rum” coconut sauce. They also have, as the name suggests, plenty of rum drinks, so try their signature Sanibel Sunset with Calypso Spiced Rum and Don Q Coconut Rum with a splash of Amaretto, orange juice, pineapple juice, and grenadine.
  • Noble Crust – Nobel Crust isn’t your typical pizza joint, rather they call it “Deep South Italian”, mixing southern fresh ingredients with Italian recipes. Here you can get starters like the decadent F.G.B.L.T. which is fried green tomatoes, Tabasco-honey glazed pork belly, and pimento cheese. And of course, you have to get one of their fire oven pizzas, like a traditional margehrita or something more exciting like the Peach + Burrata with pesto, Gorgonzola, caramelized onion, fresh peach, torn burrata and balsamic honey.
  • The Mandarin Hide – If you want a break from the beachside tiki bar and want to go all out on some of the city’s best cocktails, head to the Mandarin Hide. This little cozy, dark cocktail lounge with sparkling chandeliers is known for its expert mixologists and its Insta-worthy (and equally delicious) drinks. Each Tuesday they create an entirely new cocktail menu, so while I can’t tell you what will be on it when you visit, you know it’s going to be new and amazing. They even have aged cocktails. This place is legit, ya’ll!
St. Pete Beach at twilight with a colorful sunset in St. Petersburg, Florida
Just think, you could be overlooking sprawling beaches at sunset! (Photo Credit)

Where to Stay in St. Petersburg

Since St. Pete is so much beach, you’ll definitely have the opportunity to be a beach bum for the weekend! Here are some great beach options for your getaway:

  • This blue beach condo is overlooking the Gulf of Mexico and is just steps from the beach. You can sit on the balcony and drink as the sun goes down (or rises, if that’s your thing) and cook in the nearly full-sized kitchen.
  • Though this colorful condo is not facing the beach, you’ll be there in just a few steps. This rental is also bigger, giving you a separate living room/kitchen and bedroom if you want to spread out a little more.

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Lightner Museum, St. Augustine, Florida-Blog Photo-2
The Lightner Museum in St. Augustine is just the tip of the historic city iceberg. (Photo Credit)

St. Augustine: A History Lover’s Getaway

St. Augustine is not only Florida’s oldest city, it’s also the oldest continuously occupied European settlement on the continent, i.e. the country’s oldest city! It goes without saying that history (and ghosts!) abound here.

St. Augustine sits on Florida’s northeast coast, where Pedro Menendez — sent by King Phillip II of Spain, landed in 1565. The king sent instructions to gain control of the area, which had previously been inhabited by the Timucua Native People, and establish it as a military outpost and Catholic missionary base. 

Today it’s a city full of beautiful Spanish colonial architecture, gorgeous natural parks, and historical attractions. Get ready to eat classic Florida fare, lay on the beach, relax in nature, and get the heebie-jeebies in this historic and haunted city. 

Castillo de San Marco National Monument st augistine florida
Exploring the Castillo de San Marco National Monument is like stepping back into the 17th century. (Photo Credit)

Things to Do in St. Augustine

There is a lot to do in St. Augustine, so it was tough to narrow it down. But you’ll definitely want to get a heavy dose of history and spooky time in this centuries-old coastal city.

  • Explore the Castillo de San Marcos – Built in the late 17th century, the Castillo de San Marcos is the country’s oldest masonry fort built by the Spanish to protect themselves from pirates, Native American tribes, and other imperial powers. Come see the 20-acre fort, with its 33′ tall walls peppered with holes from invasions. Since the fort was built with coquina, a type of sedimentary rock made of shells and dead marine life, the fortress never cracked, rather absorbed cannonballs which can still be seen in the walls today.
  • Marvel at the Historic Lightner MuseumSince we are talking about the country’s oldest city here, St. Augustine has a lot of museums. One of the most fascinating, and certainly the most beautiful, is the Lightner Museum, which is housed in the old hotel Alcazar, a Spanish Renaissance Revival style building built in 1887. So let’s just say it’s ornate. Inside it’s kind of what you’d imagine an eccentric Victorina collector would have – gilded-age cases displaying shells, rocks, Native American artifacts, old instruments, Tiffany glass, and oh, a mummy and a shrunken head.
  • Get Scared on a Ghost Tour – Since St. Augustine is such an old city, it’s no wonder that it is filled with plenty of stories of those who have never crossed to the other side and still reside in this historic place. Take an hour and a half long walking ghost tour which will take you to the Old Fort and cemeteries, or, if you like to mix scary stories and booze, take the two-hour “Spirits with the Spirits” tour to get your buzz and boo on.
octopus dish at odd birds in st augistine florida
Odd Birds also has some odd dishes, like their Jimmy Grilled Out made with octopus! (Photo Credit: @odd_birds)

Where to Eat & Drink in St. Augustine

Just because you’re in the oldest city doesn’t mean you have to eat old-style food! St. Augustine has some modern easts in some beautiful spaces. Some of our favorites are:

  • The Floridian – The Floridian is just that – Florida-themed to the gills! Inside there are plenty of plants and tiki-inspired decor, as well as a beautiful patio to eat outdoors. They say their food is “innovative southern fare for omnivores, herbivores, and localvores.” Try the Not Your Momma’s Meatloaf Sandwich or the Fish Camp Fancy Sandwich, and you can bet every bite is local and fresh!
  • Odd Birds Cocktail Lounge & Kitchen – This super kitschy, tropically delightful restaurant and bar is the place to get special cocktails like The Wild Moon Child, with Tequila Blanco, Strawberry Syrup, Cynar, Pineapple Juice with a dash of Lemon Juice or an Espresso Martini to pep you up. Food-wise, they have signature entrees like their Jimmy Grilled Out with grilled octopus, papa bravas, chimi, vinaigrette, and nata.
  • Cousteau’s Waffle and Milkshake Bar – If your sweet tooth gets a hankering, head to Cousteau’s Waffle and Milkshake Bar in historic downtown St. Augustine which is just as divine as it sounds. Get a waffle like the Whirly Bird topped with fresh cinnamon apples, vanilla ice cream, caramel drizzle, and bourbon whipped cream, or a milkshake like the Pele Dos Santos with vanilla ice cream, fresh bananas, and Nutella. Or get both!
St. Augustine, Florida sunset with sailboats on the water
St. Augustine, Florida sunset with sailboats on the water.

Where to Stay in St. Augustine

St. Augustine, being an old, old place, requires you to stay in some historic and charming old places yourself! Here are some fantastically adorable options to get your in the spirit:

  • This gem in the historic district is so effing cute you’ll want to call it home before you leave. This first-floor apartment has one bedroom, a kitchen, and plenty of space. Sit on the screened-in porch and watch sailboats in the harbor and shrimp boats bringing in their catch, and watch the sunset paint the sky.
  • This 1920s 900sq/ft apartment is huge, gorgeous, and bright and is the perfect place to make your “home” for your weekend getaway. You’ll be under a mile from the Castillo de San Marcos and all the best St. Augustine has to offer.

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33 Quirky Things To Do In Key West, Florida (& Massive Travel Guide)

Paradise beach at Fort Zachary Taylor Park, Key West. State Park in Florida, USA.
Paradise beach at Fort Zachary Taylor Park, Key West. State Park in Florida, USA.

Key West: A Tropical Lover’s Getaway

Key West, Florida may be one of the most unique places in America: roosters roam the streets, drag queens rule the nightlife, and Cuba’s close proximity colors its history. The entire island is a colorful, tropical feast for the senses. Is this paradise? I thought it would be less …. weird?

To really appreciate Key West in all of its quirky glory, you also have to get to know its long history of pirates, bootleggers, and nonconformists; its resident ghosts and grave-digging iguanas; and the resident animals like six-toed cats who call it home. It’s also the southernmost point of the US, so it makes sense it’s the last on our list!

We also have a whole post about things to do in Key West if you’d like to learn even more!

Ernest Hemingway House in Key West, Florida

Things to do in Key West

Key West is where famous writer Ernest Hemingway once lived, where you can snorkel, and the sunsets are ones to remember!

  • Visit the Hemingway House & Museum – The Hemingway House & Museum is in Old Town Key West, and this yellow, airy, many-windowed home is in the French Colonial style with many art deco accents on the inside. This is a really big attraction on Key West for good reason – Hemingway was a prolific writer during the 1920s and 30s, and he wrote two of his most famous books in this very house: A Farewell To Arms and To Have and Have Not. Ernest Hemingway lived in Key West for years, making the island his permanent place of residence in the 1930s, and is the man who I have decided to fully blame for all the cats on the island (according to the official website, more than forty cats, who are all named, live here).
  • Snorkel at Fort Zachary Taylor State Park: The only reef you can reasonably swim to in Key West is the one in Fort Zachary Taylor. The admission for pedestrians is $2.50 and you can spend the entire day here – there’s not only swimming, but the park is known for having many tropical species of birds you can see like the Roseate Spoonbill. These reefs may be your best chance to catch a glimpse at the elusive sea turtle as well! Since you will be on your own in this reef, make sure you bring your own snorkeling gear or rent one at the park (either way, pack anti-fog spray).
  • Take a Sunset Cruise – A sunset cruise cannot be missed in Key West, and they normally give out free beverages – because Key West is always down to party – and are the absolute best way to see the sunset. Most of these tours are about two hours long, returning at around 7pm. Note that since these are sailboats, the downstairs space of the boat is pretty much just a bathroom and not a space to hide from the sun, so if you burn as badly as I do make sure you bring sunblock! If you’re traveling with your partner, book an intimate cruise like Danger’s Charters Wind & Wine Sunset Sail Sitting on a boat and watching the sunset together is such a romantic way to spend time with each other! For a livelier evening, Cool Key West is a great choice, with local musicians playing and plenty of free drinks.

Where to Eat & Drink in Key West

Key West, besides being a veritable paradise, has some delicious food options to match. And some drinks with character!

  • Grab Breakfast and a Show at Blue Heaven – Blue Heaven is really easy to miss (look for the sign on a gate behind some bushes), but eating at this outdoor restaurant feels like you’re inside a jungle shaded by massive banyan trees, banana palms, and colorful hibiscus flowers. The restaurant is home to cats, chickens AND baby chickens, so you just might make some animal friends while you eat! Try their Lobster “BLT” Benny – a spin on the classic BLT but with fresh lobster. Blue Heaven also has a Rooster Graveyard, which contains the remains of cockfighting roosters and some of Blue Heaven’s more recent rooster residents. Every morning Blue Heaven hosts local musicians playing calming music to help you start your day on the island, so grabbing breakfast here is sure to get you in the island spirit.
  • Get a Drink and See a Drag show at 801 Bourbon Bar – 801 Bourbon began in 1987 as a piano bar, but as time went on, the focus became less on the piano and more on the drag performances. Just one thing: at 801, the queens don’t lip-sync! They are great singers and you can listen to them sing and dance before the comedy portion of the show. Fair warning: if you’re in the front rows, you’ll probably get teased by the queens. But hey, getting made fun of by a drag queen in front of a live audience is a gift.
  • Dessert that’s Better than Sex: Better Than Sex is THE romantic dessert date spot to go to. While it has recently expanded out of state, this is the original and where the owners reside, so you should stop here at least once to get some sweets. I am a big lover of dessert, and let me be the bearer of good news: Better Than Sex has desserts that make me weak in the knees. Most of the desserts have fun names, like the Kinky-er Key West Cream Pie, a good locally-themed choice. Their cake is also amazing – fluffy slices piled high with icing – with delicious caramel and raspberry drizzles that, I am not ashamed to admit, I happily drown my cake in. Yum!
The backyard of an AirBnb in Key West Florida with a hot tub.
There are plenty of little paradises you can rent in Key West! (Photo Credit)

Where to Stay in Key West

One key thing to note, though: although there are plenty of home rentals on the island, local regulations require a 28-night minimum stay. So if you’re not a remote worker looking for a month in paradise, you’ll want to book a hotel, resort, condo, or properly licensed vacation rental.

  • The charming Wicker Guesthouse is located just one block from the Ernest Hemingway House, with a tropical garden and an outdoor pool. Rooms include microwaves and a small fridge, you can rent bikes on-site, and you’re only a 10-minute walk from South Beach.
  • The Secret Garden offers a charming private oasis, with two bedrooms, a fully stocked kitchen, and access to a shared pool.
miami beach florida-Blog Photo-2
Get ready for beach time! (Photo Credit)

What to Pack for Weekend Getaways in Florida

Here’s what to pack in your luggage to bring with you to the beach:

  • Several Swimsuits: There’s a good chance you’ll be jumping into the water every day, so you’ll want to bring along multiple pairs of swimsuits so you always have something dry to put on! I’m a size 16/18, and my favorite swimsuit is this one, which I literally have in 3 different colors. It’s amazing. It’s perfect. It’s a freakin’ steal! I also love this suit, and this is my favorite one piece. For more swimsuit picks, check out my guide to swimsuits for curvy girls.
  • Travel Towel: There is absolutely no guarantee that the towels at your accomodation are going to fit around your waist. Frankly, they rarely fit around my left thigh. Plus, they’re heavy and bulky and you can get in trouble for bringing them out of the hotel. So just to be safe, I always bring my own travel-friendly, lightweight, quick-drying travel towel!
  • Travel Clothesline: Newsflash: your hotel’s moist, dark bathroom is the absolute WORST place to hang your clothing up to dry. Instead, hang this tiny travel clothesline up somewhere that gets plenty of airflow and sun, like on a curtain rod in front of the window! Your wet swimsuit and travel towel will be dry in no time.
  • Sand Repelling Beach Mat: I hate sand SO MUCH and this mat is made with magical sand-repelling qualities. If sand doesn’t make you want to go live in an igloo forever, you can always just use your towel as a mat instead!

On beach days, we pack up our day bag with all of our beach gear and a full bottle of cold water to stay hydrated (our insulated water bottle keeps water cold for an unbelievably long time). And of course, lots and lot of sunscreen – don’t forget to re-apply!

For more beachy packing tips and curvy-girl specific suggestions (ahem: do you have chafe balm yet??) head over to our beach vacation packing guide!

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About the Author: Richie Goff is a Louisville, Kentucky native with a great love of the outdoors. When he is not growing flowers for fun, he is the Editor-in-Chief of Practical Wanderlust and Let’s Go Louisville. He has been a friend of Lia’s since high school, and they have taken plenty of their own disaster-prone adventures together!


Which of these weekend getaways in Florida excites you the most? What are you most excited to do? Drop us a comment below!

Looking for more Florida inspiration? Check out our other posts:

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Our Top Travel Tips & Resources

Here are our favorite travel tips & resources for saving money and planning travel logistics! For more tips, check out our travel tips resource page or our guide to planning a trip.

  • Booking Flights: To score flight deals, search on Google Flights or Kayak. Money-saving tips: fly mid-week or on the weekend; fly carry-on only on a budget airline; and take red-eyes or early morning flights.
  • Accommodations: We usually stay in budget-friendly vacation rentals, boutique hotels or private rooms in hostels. We use Booking.com to book hotels (we love their flexible cancellation policy) and Hostelworld to book hostels (low deposit, easy change/cancellation, and excellent reviews). For vacation rentals, we prefer to book using VRBO because they’ve got lower fees and better support than Airbnb, and we’re not fans of Airbnb’s unethical track record. You can also book vacation rentals on Expedia and Hotels.com. We also use TrustedHousesitters as both hosts (for our home and our fur-child) and travelers!
  • Travel Insurance: We always, always, ALWAYS buy travel insurance for international trips, and we STRONGLY suggest it – visit our Travel Insurance Guide to find out why. We recommend either World Nomads or SafetyWing for international travel insurance. SafetyWing is one of the few policies that covers Covid-19, and they have excellent monthly policies that are perfect for Digital Nomads and long term travelers!
  • Travel Credit Card: We book all of our trips on our favorite travel credit card. Not only do we earn cash back that we can spend on more travel, but the card offers fantastic travel perks like travel insurance, trip delay and cancellation coverage, lost baggage reimbursement, and rental car coverage, which helps protect us on our travels. Learn more here.
  • Vaccines & Meds: We use the travel guides on the CDC website to research recommended medications and vaccines for international trips. We always recommend getting every vaccine recommended by the CDC! You can get them at your primary care doctor’s office or a walk-in pharmacy.
  • Tours: We love booking guided tours, especially food tours and walking tours, to get a local’s perspective and a history lesson while sight-seeing! We book our tours using Viator and GetYourGuide.
  • Transportation: We use Rome2Rio to figure out how to get from place to place, and book local transportation online using Bookaway wherever we can. When we book a rental car, we use Kayak to compare rental companies and find the best deal.
  • Luggage Storage: Whenever we’re checking out early or taking advantage of a long layover, we use LuggageHero to safely store our luggage while we’re running around. Use the code PRACTICALW for 2 hours of free luggage storage on us.
  • VPN Service: A VPN keeps your digital information (like website login details, bank info, etc) safe, even when you’re connected to an unsecured network while traveling. Plus, it lets you use Netflix & other streaming sites abroad! We use NordVPN. Use the code WANDERLUSTPROMO when you sign up!
  • What to Pack: Here are the travel essentials that we bring on every trip. We also have packing lists for hot weather, cold weather, and many more. Take a look at all of our packing guides!


Richie Goff

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