Updated: Jul 16, 2021
Key West is at the southernmost point of the Florida Keys and even the continental US! Known for its "One Human Family" motto of inclusion, the beautiful tropical climate, and endless experiences in paradise, it is easy to see why Key West has been a hot spot for tourism for decades now. With the island taking pride in its history, and vibrant nightlife it has long been a safe haven for the LGBTQ+ community and open minded individuals alike.
It is around a 3.5 - 4 hour drive south of Miami. While the drive is very scenic and beautiful, it mostly consists of one way streets on either side which can easily back up with traffic, so plan accordingly and make sure to give yourself plenty of time to/from if you're commuting from Miami. If you didn’t want to make the drive you can also take flights to the Key West International airport which is less than a half hour flight away from Miami.
If you’re driving from Miami International Airport, you will drive LeJeune Road south to 836 West. Take the Florida Turnpike south toward Key West. The Turnpike ends at US 1 in Florida City. Follow U.S. 1 south as far as it goes and you will eventually make it to Key West.
Key West History
Key West is a beautiful island within the Florida Keys where tourists travel from all around the world to visit year after year. It is located close to the equator meaning you can expect tropical climates year round. The architecture, weather, and vibe of this city will have you feeling like you are on some international renowned island. With the word cayo translating to key in spanish, Cayo Hueso is the original Spanish name for Key West. Hueso, meaning bone in Spanish, was for the Tequesta and Calusa native tribes who inhabited the island prior to any western settlers. With Key West being so close to sea level, natives were not able to bury their deceased and were said to have littered the bones of those who passed away across the island as a memorial, hence the Spanish settlers naming it Cayo Hueso.
LGBTQ+ Community and Impact
Key West became a well known LGBTQ+ destination especially during the AIDS crisis throughout the 70s and 80s. Gay men and women across the country were hearing of Key West as being an island of inclusion, charm, and acceptance and they relocated to Key West to live out their days in this beautiful paradise. It is said that the AIDS rate was even higher here compared to New York City or San Francisco during that time which was causing concern from the local governments that it would negatively impact tourism.
Many of these queer people starting forming their own LGBTQ+ community and businesses throughout the island in order to preserve the economy, tourism, and community here. Over time this has continued to grow, making Key West one of the most accepting LGBTQ+ destinations in the US.
Make sure you stop by the Gay Key West Visitors Center and meet Fritzy! Gay Key West Visitors center has over 500 businesses and members in support of the LGBTQ+ community and counting! This is pretty incredible considering Key West is only 2 miles by 4 miles in size. It is so beautiful to see just how the LGBTQ+ community has taken its hardships and put so much love, care, and acceptance in to this island and we hope it continues to set the goals for other cities around the country.
Top Things to Do
Dolphin Watching and Snorkeling w/ Honest Eco Tours
Jump on board of Squid, the first fully electric passenger boat in the USA! On this four hour nature tour with Honest Eco you will start by learning about sustainability, the history of the Key West, marine life, and more! As you take off out of the harbor, your dolphin watching will begin. This tour has over an 85% dolphin spotting percentage which is pretty amazing considering they are wild animals who come and go as they please.
Not only do you get a chance to see dolphins, but you will also be going snorkeling! You will get plenty of time to hop in the water and swim around for a chance to spot sting rays, turtles and many different fish. Fun fact, Key West is home to the third largest barrier coral reef in world (the first being the Great Barrier Reef in Australia), and the largest in the United States!
Jet Ski Island Tour w/ Barefoot Billy's
This 90 minute jet ski tour is the perfect day activity for all you adrenaline junkies! At Barefoot Billy’s they will take you and a group of other jet skiers out on the water and drive around the island. Along the way, you will learn about the island’s ecosystem, the mangroves and get a unique view of Mallory Square from the water. This was my first time being on a jet ski and the instructors made me feel safe and taught me how to drive in no time!
Keep in Mind: Florida State law, all boaters born in 1988 or later must take Florida's Boater's Safety test before your tour. Don't stress, it isn't a hard test! Arrive at least an hour early so you have plenty of time to finish up the test to avoid cutting in to your tour time.
Stroll Around Mallory Square
Key West is known for it's beautiful sunsets and if you are looking for a prime spot on the island to watch, we recommend Mallory Square. Located at the historic waterfront, you can watch street performers, fire dancers, food stands and more every night during sunset. Mallory Square is also home to shops, restaurants and plenty more for entertainment!
Blu Q Sunset Sail
Another fantastic view of Key West's famous sunsets is on the Blu Q Sunset catamaran, an LGBTQ+ favorite activity in the Key West. It has been known as the home on the water for the LGBTQ+ community since 1996! The cruise is BYOB/snacks and you’ll join other queer members for this 2 hour boat ride across the waterway. This catamaran also has the famous “trampolines” which are the nets you can lay out on while you watch the sunset.
Blu Q also hosts a sandbar and snorkeling tour during the day, which is another awesome tour to meet others in the community while enjoying a unique Key West experience.
Kermit’s Key Lime Pie
You will catch on very quickly that every restaurant in Key West claims to have “the world’s best Key Lime Pie" recipe. Take it from us, we tried at least 15 different ones while we were in town! Hands down though, the best one we had was at Kermit's. Kermit's is located in the historic Key West Bight near Mallory Square and is home to the best Key Lime Pie starting in 1993. Not only does this cute shop have the OG pie slice, but you MUST try the Chocolate Dipped Key Lime pie on a stick. No I didn’t stutter…chocolate dipped key lime pie! It is honestly for the best we didn’t try this until our last day in Key West because we would have definitely had about 10 more if we could have!
Kayak the Mangroves w/ Get Up and Go Tours
Located at the Sugarloaf Marina, you can rent a single or two person clear kayaks for 2+ hours and explore with the Get Up and Go tour group. This tour starts only a short 25 minute drive away from Key West and you will get the best seat in the area for getting an up close view of the mangroves! We were taught all about the mangroves and the wildlife around the area. Make sure you keep an eye out! You could get lucky enough to see baby sharks, turtles, stingrays, coral, and other marine/ wildlife.
Ernest Hemingway House Tour
Key West has been called home by many writers, artists, and musicians over the years. This is due to the open minded and creative nature of the city mixed with the tropical paradise vibes. Doesn't that sound like the perfect concoction for inspiration to you too?? On this tour you will get to walk through the home of American Novelist, and Nobel Prize winner, Ernest Hemingway. You will also get a peak at the room where most of his most famous works were written.
Key West Lighthouse & Keeper's Quarters
The current lighthouse opened in 1848 and was operated by a woman, which I am sure you could guess was practically unheard of during the 19th century. Today, the lighthouse stands as a museum and tribute to those who operated the lighthouse over the years and got Key West through wartime and bad weather.
Southernmost point of the US Landmark
Did you know that Key West is the furthest south you can go in the USA? Well, if you do not believe me you can visit the landmark here in Key West that proves it! I still cannot believe that Key West is actually closer to Havana, Cuba than Miami.
Where to Stay
Key West is only 2 miles by 4 miles big and considered a very safe destination, so it is not like you can necessarily choose a "wrong area to stay in" while visiting Key West. However, we definitely recommend staying near the heart of Key West aka "Old Town". Staying in Old Town will give you the true Key West charm with the Conch-Style houses, the tropical forestation, and being within walking distance to all the best things to see!
We could have spent a month at this guesthouse and it would have simply not been long enough. Alexander’s is an award winning LGBTQ+ charming guesthouse located at the heart of Key West in Old Town. The guesthouse is a traditional conch-style home, which is basically a blend of Victorian and tropical architecture. All members of the staff are absolutely amazing and will make you feel like family from the moment you arrive! Alexander's takes pride on inclusivity and making sure their guests feel as comfortable and safe as possible while being their true selves.
Alexanders has a pool and pool bar on site with multiple decks to sunbathe on. They offer free breakfast, snacks throughout the day, and a family happy hour from 4:30-5:30 for you to mingle with the other guests by the pool.
Kimpton Winslow Bungalows
This is your private oasis tucked away for an incredible tropical stay! Kimpton Winslow Bungalows is located in Old Town and just a short walk away from the busy bar street Duval and the gay district. The pathways to your bungalow will make you feel like you are in a jungle, and your private bungalows are quaint and quiet.
They offer a free breakfast bar every morning for its guests and also have two pools on site for you to enjoy some sun bathing during your down time.
Where to Eat
Half Shell Raw Bar
After you finish one of your tours at the marina, make sure you walk right over to Half Shell Raw Bar! This popular restaurant has been thriving since 1972 and offers some of the best seafood in Key West. This is a favorite restaurant by the locals and fisherman and will give you a taste of old Key West. If you are sitting by the pier side, look down at the water from time to time for a chance to see tarpons, manatees and other fish passing through. Our favorite dish was the lobster egg rolls and mussels.
Matt’s Stock Island
Matt's Stock Island Restaurant and Bar is located inside of The Perry Hotel, only a short 15 minute drive outside of Old Town Key West. The patio is romantically facing the pier where you can check out all the beautiful yachts docked up. Matt’s is known for its Grouper Gnudi and woooo it did NOT disappoint. This dish was easily one of our favorites in Key West! Their Key Lime Pie also made it on to Forbes Top 5 Key Lime Pies found in Key West, so you already know you have to leave some room for desserts and give it a taste!
Bistro 245 restaurant at Opal Key Resort & Marina is a beautiful location on the edge of the Gulf of Mexico. Start with a glass of wine and the lobster quesadillas as you watch the sun hide behind the horizon. If you are looking just for drinks, stop by their truck bar and watch their nightly drumming musician. Make sure to make a reservation in time for sunset.
Poke in the Rear
Located at AquaPlex, Poke in the Rear has the best poke bowls we have ever had! Elle's Poke's on Fire is super fresh and tasty, and if you aren’t a big seafood lover try the Short Rib poke. The short rib poke has been on my mind since that first bite it was so delicious!
Fun fact: most of their poke bowls are named after the famous Drag Queens from Key West!
Built in the 1800s and then later turned in to a restaurant in 1979, Bagatelle will have you feeling like you took a step back in time. We picked the perfect view from the second floor patio where we could people watch while we enjoyed our meal. They are known for their lobster mac and cheese and trust me, order it, you’ll know immediately why they are known for it. It is so tasty!
Where to Drink
Drag Show at Aqua Bar
Aqua Bar at AquaPlex has hilariously entertaining and fun drag performances starting at 9 pm. The islands top drag talent perform each night for an experience you don't want to miss. You can make your table reservations online or in person, but just do it ahead of time as the tables sell out quickly!
22 & Co
Glitter cocktails? Tutus lovers? What more could you ask for! 22&Co is an LGBTQ+ owned cocktail bar located within AquaPlex aka right next to Aqua bar and Side bar. You have to try their famous Peanut Butter milkshake it is a boozy delight! PS this place had the cleanest bathroom I had ever seen at a bar, bravo!I
Key West's newly renovated dance bar, Sidebar, is the place to get your dance on. Good music, lights, and fun. With nightly DJs and events you can be sure to have a good night out with friends here!
Marilyns Drag Brunch & Bingo
Who doesn’t love a drag boozy brunch combined with bingo?! Marilyn's is the perfect place to work off your hangover from the night before while you get bottomless mimosas and their tasty cinnamon rolls. Sundays they host drag bingo where one of the famous Key West talent will perform and you have a chance at winning some prizes or a shot or two.
Say hi to Laurie, the best bartender in town for us! (far right pic)
Walk Around Duval Street
Duval street is where all of the popular bar crawling happens. Stretching up to a mile long in Old Town you can walk from bar to bar and check out the scene. You can find plenty of live music, restaurants, and more every night here! Keep an eye out for the history signs as this is a part of Old Town Key West!
Bobby's Monkey Bar
Looking for a late night spot where you can sing your heart out? This LGBTQ+ friendly karaoke bar is the perfect place for you! This spot is a local's dive bar mixed with good music and a whole lot of fun! (Check out the monkey's hanging behind the bar!)
Key West Fun Facts
You pronounce Conch like “Konk” which are the beautiful pink seashells. The local natives are also referred to Conchs, and you can also find Conch-style homes all across the island.
Key West is located at the closest point to the equator in the USA
Key West is closer to Havana, Cuba than it is Miami
We loved these facts and there are plenty more! Check out more of the Key West fun facts here.
With much of Key West's history being influenced by the LGBTQ+ residents over the past decades it is known to be a safe haven for the community. Most bars, restaurants, and excursions will be LGBTQ+ accepting or owned throughout Key West. The island's motto for "One Human Family" represents the importance of love and respect for one another no matter who you are or who you love.
Key West also hosts many LGBTQ+ accepting events every year such as the Pride parade, WomenFest and Fantasy Fest where you can come and celebrate love with all of the other locals and travelers. This island is an excellent vacation spot and we cannot wait to go back!
Huge thank you to The Florida Keys for inviting us and hosting such an incredible trip!