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Road trip across the Florida Keys to Key West | A Gay Couple on the road

Road trip across the Florida Keys to Key West | A Gay Couple on the road

Wake up to the crowing of free-range roosters, eat key lime pie for breakfast, sunbathe naked by the pool at the world’s best gay resort, snorkel the world’s third-largest tropical coral reef, and watch the sunset over the Gulf of Mexico. The Florida Keys archipelago is considered one of the most fantastic, LGBTQ+, and gay-friendly destinations in the USA. As an openly gay couple traveling, we spent ten days on the islands and in Key West. As well as hitting the gay bars and drag shows in Key West, we also enjoyed parasailing, snorkeling, and kayaking as part of a visit to this water sports and seafood paradise.

paid collaboration with the Official Florida Keys Tourism Council –

Photo with a Mural: Grettings from Key West, Florida - and the Cuban Coffee Queen © Coupleofmen.com
Greetings from Key West in Florida – and from the Cuban Coffee Queen © Coupleofmen.com

As a gay couple traveling in the Florida Keys

Having visited Orlando and the south of Florida with Miami and Fort Lauderdale in previous years, the time had finally come for us to visit Key West and the group of over 200 coral islands that make up the Florida Keys. “Key Largo, Montego … Off the Florida Keys (…)” – With Kokomo by The Beach Boys on the radio, we drove towards the sun and the southernmost point of the United States of America in our rental car, singing and with the windows open. When we reached the Overseas Highway, the southernmost section of U.S. Highway 1 in Florida, with Key Largo, we were surrounded only by the sea, the Gulf of Mexico on the right and the Atlantic Ocean on the left. So, our adventure in the gay friendly Florida Keys could finally begin…

Wasser, nichts als Wasser - Blick über den Overseas Highway 1 in Florida © Coupleofmen.com
Sea, nothing but blue sea – and the view over the Overseas Highway 1 in Florida © Coupleofmen.com
Flying with KLM Royal Dutch Airlines © Coupleofmen.com

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Islamorada: First stop on the Keys

About halfway between Miami and Key West, after a good two hours of driving on the hectic highways of South Florida, we reached our first stop on our road trip through the Florida Keys: Islamorada. The 28 km-long community, nicknamed the “Village of Islands”, comprises six successive islands and is best known as a fishing and water sports resort. But for us, there was only one thing to do on this sunny day: to arrive. To wit: Check into the hotel, put on our swimming trunks, and head for the pool! Mild, turquoise, crystal clear water in the pool and the bay under palm trees… Yes, we could enjoy ourselves here at the southern tip of the Florida peninsula.

Gay Florida Keys Couple Selfie Hotel Pool Islamorada © Coupleofmen.com
Welcome to the Paradise of the Gay Florida Keys © Coupleofmen.com

Postcard Inn Beach Resort and Marina – Islamorada

The resort is situated next to a small harbor, right on the sea. We summer holidaymakers were accommodated in an ocean-view room with two queen beds. Here we spent relaxing hours by the pool, with the best summer hits playing from the speakers throughout the resort. From the balcony, we had not only a spectacular view of the azure blue Atlantic, but also a fantastic sunrise the following day.

We planned our dinner at the restaurant “Ciao Hound Italian Kitchen & Bar“, with delicious pasta dishes that we can also recommend to vegetarians.

Marathon: Second stop in the Keys

After a wonderfully relaxing night with open windows and the sound of the sea as natural lounge music, the following day was all ours. Hand in hand, we sat on the balcony, watching the spectacular sunrise. Countless seabirds gave us a good morning concert. Even a pelican plunged into the water, only to emerge quickly with a fish in its beak. How quickly the light changed… The calm sea was particularly remarkable. We could barely see a wave. Suddenly, out of nowhere, the fin of a Caribbean or nail manatee emerged from the sea. Just one? No, three of them were playing in the shallow water near the shore while other early risers took the opportunity to capture some holiday memories on their mobile phones.

Meet and Greet mit einem Manatee in freier Wildbahn © Coupleofmen.com
Meet and Greet with a “Manatee” in the wild © Coupleofmen.com

Visiting the Turtle Hospital on Marathon Island

Unfortunately for us, it was already time to leave with our bags packed. After we checked out, we were on the Overseas Highway heading south again. We had an appointment at the hospital. Not just any hospital. But at the Turtle Hospital. The Turtle Hospital on Marathon Island is a non-profit organization dedicated to rehabilitating endangered sea turtles. Curious about the work of the small NGO, we arranged to meet Bette Zirkelbach at the hospital’s entrance.

Karl vor dem Eingang des Turtel Hospitals in Marathon © Coupleofmen.com
Karl in front of the entrance to Turtel Hospital in Marathon © Coupleofmen.com

“Take as many photos and videos as you need. Nature needs our help – and we need the help of our visitors. Not only do we rescue injured and sick turtles. We’re also dedicated to finding the cause of life-threatening diseases that are on the rise in Florida’s highly populated areas.”

Bette Zirkelbach

As soon as we enter the former motel building, which is located directly on the Overseas Highway, we are taken on a little tour through the history of reptiles in Florida by educational posters and huge actual turtle shells. We were impressed and couldn’t wait to learn more from Bette about this special place of animal conservation.

Daan studiert die Informationen zu den verschiedenen Schildkrötenarten in Florida © Coupleofmen.com
Daan studies the information about the different species of turtles in Florida © Coupleofmen.com

The work of the Turtle Hospital

At the Turtle Hospital, turtles injured by motorboats or suffering from fibropapillomatosis (a disease caused by herpes viruses) are treated and operated on. They can be rehabilitated and, ideally, released back into the wild if possible. We were able to see this firsthand. Behind the entrance building, there are extensive saltwater tanks and a pool where the shell-protected patients are preparing for or recovering from surgery. Here we had the opportunity to get up close and personal with these fascinating sea creatures. But caution was advised: Turtles are susceptible to their environment, and touching them by unauthorized people is punishable by law.

Gay Florida Keys Turtle after surgery with Bette Zirkelbach © Coupleofmen.com
A turtle after an operation with Bette Zirkelbach © Coupleofmen.com

“All healthy animals we encounter in the wild should be left undisturbed. However, if a turtle can no longer dive, is bleeding or has some other injury, the coastguard should be called. It is important not to leave the animal alone because currents can quickly transport the animals further along the coast. If the turtles are small enough, we will explain on the phone how to bring the animals safely on board. If the animals are too big, we take over the job.”

Bette Zirkelbach
Gay Florida Keys Turtle hospital Turtle Selfie with Bette Zirkelbach © Coupleofmen.com
Turtle selfie with Bette Zirkelbach at the Turtle Hospital © Coupleofmen.com

If you think the Turtle Hospital is a government organization, you are mistaken. Apart from donations, which have to be raised through hard publicity work, the protection of the sea turtles depends mainly on entrance fees from tourists and income from tours and educational projects. We take the advice of biologist Bette Zirkelbach to heart. And so should every traveler, not just to the Florida Keys, but in general. The motto is: take pleasure in admiring the beautiful creatures from afar. But that’s about it. Touching or feeding them is strictly prohibited!

On the following page, you will find the most important telephone numbers where you can get help in a turtle emergency: Sea Turtle Emergency >

Isla Bella Beach Resort – Marathon

Palm trees as far as the eye can see. Tucked away in the center of an artificial palm forest, we stayed at the Isla Bella Beach Resort. The spacious suites with sea views are decorated all in white and gave us a real summer holiday feeling. Of course, this also applied to the hotel’s swimming pools and the possibility of renting bicycles for two hours free of charge.

For dinner, we had a reservation at the restaurant “Mahina” with had a view over the adjacent bay. This a tip for lovers of fish dishes – but not necessarily suitable for vegetarians.

Gay Florida Keys Hand in hand in front of the Isla Bella Resort in Marathon © Coupleofmen.com

Sunset from the historic Old Seven Mile Bridge

As tempting as the resort’s pools were, we opted for a different, exceptional excursion. Equipped with a camera and our tripod, we set off to explore a section of the famous Old Seven Mile Bridge on foot. The bridge, which runs parallel to the Florida Keys Overseas Highway in the Middle Keys, offers a spectacular view of the Gulf of Mexico. We were lucky: a sea turtle emerged from the water to our right after just a few minutes, only to disappear back into the depths. Seeing a distant relative of Crush from “Finding Nemo” in the wild was a fantastic feeling. We walked hand in hand across the bridge, which pedestrians and cyclists almost deserted. As a bonus, we managed to get some unique photos of our first sunset in the Gay Florida Keys.

Gay Florida Keys sunset on the Old 7 Miles Bridge © Coupleofmen.com
Sunset on the historic 7 Miles Bridge © Coupleofmen.com

Kayak Tour with Big Pine Kayak Adventures

After a restful night, we headed south the following day with a coffee to go (in the metal cup we brought with us from Amsterdam, of course). Half an hour later, we found ourselves on the island of Big Pine Key in a red kayak from Big Pine Kayak Adventures. We love being outdoors and learning firsthand about the fragile ecosystems of this world.

Daan kayaking through the Mangroves with Big Pine Kayak Adventures © Coupleofmen.com
Daan kayaks through the mangroves with Big Pine Kayak Adventures © Coupleofmen.com

And so, we discovered mangrove jellyfish, crabs, and sea anemones from the kayak. And we were lucky: Horseshoe crabs were also among the marine creatures we encountered. Again, the motto here was: observe live animals, but don’t touch them! At the end of our adventurous tour through the dense mangrove forests on the way to the kayak harbor, we spotted a bald eagle circling above our heads. What an insanely beautiful nature day!

Gay Florida Keys Kayak tour with Big Pine Kayak Adventures Skeleton of a Horseshoe Crap © Coupleofmen.com
Daan holds the abandoned exoskeleton of a horseshoe crab in his hand © Coupleofmen.com

Tips for your kayak adventure

Sunscreen 50+ is an absolute must! Even when the sky is cloudy or the wind is brisk, the Caribbean sun can really sunburn us Europeans. We recommend packing plenty of water and a few snacks, such as nuts.

Travel planning with TripAdvisor: Big Pine Kayak Adventures >

Gay Florida Keys Kayak tour with Big Pine Kayak Adventures © Coupleofmen.com
Kayak tour with Big Pine Kayak Adventures © Coupleofmen.com

The last leg of our gay road trip through the Florida Keys to Key West was just a 45-minute drive. Then we would finally reach the famous island city of Key West. But before we crossed the last bridge, we made a short detour to Stock Island. This island off the coast of Key West has a large marina for pleasure boats. The Perry Hotel & Marina is located here and is a popular accommodation for boating enthusiasts and sports fishermen.

The Perry Hotel on Stock Island © Coupleofmen.com
Outside of The Perry Hotel on Stock Island © Coupleofmen.com

Key West: Cocks, Water Sports & Seafood

Once mentioned in the same breath as the great city of New York, the westernmost inhabited city of the Florida Keys was an important hub for shipping traffic from the Caribbean and South America towards Europe (and back). Thanks to that, Key West owes its wealth to the coral reef and the shoals, which are dangerous for sailing ships – “thanks to shipwrecks!”. Today, the Key West Shipwreck Museum stands as a testament to this part of Key West’s turbulent history on the waters. Besides “treasures” from sunken times, we had a fantastic view over Key West from the museum’s tower.

View of Key West from the Shipwreck Museum © Coupleofmen.com
View of Key West from the Shipwreck Museum © Coupleofmen.com

But the first to greet us in the parking lot in front of our hotel was not a pirate or a sailor (unfortunately), but a rooster. Descendant of roosters from the times of Cuban cockfights, the rooster patrolled the footpath with a proud chest as if it were the most normal thing in the world. We did the same. And so, after checking into our hotel, we strolled through the so-called old town of Key West, the “Key West Historic District“, with big grins on our faces.

We didn’t expect to find such beauty in the streets and over 2,485 conch-style buildings that form the Key West Historic District. These include New England cottages, Victorian Conch-style houses, and buildings with Caribbean influences, such as those from the Bahamas. Nestled among lush tropical plants, mansions, and smaller wooden houses line the narrow streets. It is a feast for the eyes, with plenty of paths to explore on foot. Highlights include the Ernest Hemingway House, the Harry S Truman Little White House, and the Key West Lighthouse.

Sunset scenery at Mallory Square of Key West © Coupleofmen.com
Sunset scenery at Mallory Square of Key West © Coupleofmen.com

“The Best Gay Resort in the World”

THE place to stay in Key West for gay travelers: Nudist-friendly, excellent cuisine, pool, sauna, steam room & more – read our review to learn everything about “The Best Gay Resort in the World”, the Island House in Key West.

Gay men only clothing optional Resort Island House Gay Couple in Bed © Coupleofmen.com

Bike Tour of Key West with Key Lime Bike Tours

But not just on foot. In the style of our adopted hometown Amsterdam, we were keen to explore Key West by bike the next day. After all, Key West is a famous cycling city in the USA. And even the usually car-loving Americans seem to take bicycles into consideration on this island. 😉 And so, we cycled with Key Lime Bike Tours from Ann Street through the historic center, past the cemetery of Key West, to the southernmost point of the USA.

Exploring Key West by bike with Key Lime Bike Tours following the Guide © Coupleofmen.com
Explore Key West by bike with Key Lime Bike Tours © Coupleofmen.com

Even though that special point of interest, in the form of a giant red, brown, and black striped concrete buoy, is a popular photo motif, and the queue of tourists waiting for THE snapshot was correspondingly long, we contented ourselves with a photo as we drove by.

Most Southern Point of continental USA in Key West © Coupleofmen.com
The southernmost point of the continental USA in Key West © Coupleofmen.com

Back from our tour, we indulged in our first slice of key lime pie. This popular and delicious pie is made with lime juice, egg yolk, sweetened condensed milk, and a meringue crust from egg whites. You must try this local specialty at least once in the Florida Keys! We recommend the chilled version at Key West Key Lime Pie Co. Yum!

Travel planning with TripAdvisor: Key Lime Bike Tours >

Bike Selfie in Key West with Key Lime Bike Tours © Coupleofmen.com
Bicycle selfie with Key Lime Bike Tours in Key West © Coupleofmen.com

Parasailing with Fury Water Adventures Key West

When in Rome … After our aerial excursions to Namibia for skydiving, Switzerland for paragliding and Illinois, USA, for a sunrise balloon ride, we couldn’t miss a parasailing trip in Key West. We were excited when we spotted parasailers from the car, even though flying over the water behind a boat is definitely the least dangerous recreational kite activity we have tried together so far. So, in the early afternoon of a sunny Saturday, we found ourselves at the dock with three other couples, a photographer, and the captain of the Fury Water Adventures boat.

Boat in front of Parasailing with Fury Water Adventures in Key West © Coupleofmen.com
Boat in front of the parasailing chute with Fury Water Adventures © Coupleofmen.com

After a short briefing, we left the harbor at high speed before one loving couple after another was strapped into the harness and rolled into the sky at a height of around 100 meters. Then it was our turn. Karl was particularly nervous, but once in the air, all fears flew away. The silence up here and the view of the turquoise sea and the various islands off the coast of Key West was simply breathtaking… and the little foot bath at the end of the flight was a welcome refreshment.

Tips for your parasailing adventure

Sunscreen 50+ is a must, as the reflection of sunlight increases the risk of sunburn. We also recommend bringing plenty of water and a change of dry clothes. You can also take a GoPro, but it should be worn on a strap around your neck or on your head.

Travel planning with TripAdvisor: Fury Water Adventures Key West

Parasailing-Abenteuer mit Fury Water Adventures in Key West © Coupleofmen.com
Parasailing adventures with Fury Water Adventures in Key West © Coupleofmen.com

All Men’s Day Trips (clothing optional) with Blu Q

Honestly, we couldn’t stay away from the water every day we were in Key West. And we didn’t have to! Blu Q – the self-proclaimed “home on the water for gay men” – has been running sailing trips out of Key West since 1996. We were particularly attracted to their nudist-friendly, clothing-optional day trip, which included snorkeling and kayaking. Two days later, we stood with eight other young men on the Blu Q catamaran in the historic harbor of Key West’s old town.

Blu Q Catamaran for the All Male Sailing Tour around the Florida Keys © Coupleofmen.com
Blu Q Catamaran for the All Men Sailing Tour around the Florida Keys © Coupleofmen.com

Here we were greeted by the outrageously handsome captain and his sexy first officer. Woof! After a short briefing, we left the harbor. Shoes off, Prosecco in the coolers, it was time to meet the bearded like-minded people our age.

Captain and first Mate of the Blu Q All Male Sail © Coupleofmen.com
Captain and First Mate of the Blu Q All Male Sail in Key West © Coupleofmen.com

Once out of sight of the other boats, we could finally remove all our clothes and enjoy the freedom of standing completely naked on the catamaran in the wind as we cruised between the small islands off Key West. As luck would have it, one of the travelers, Chris, had a drone with him. He used it to get some spectacular video footage of us, which we will post on our Instagram @coupleofmen. A great day, totally relaxed, naked, and free. By the way, Blu Q also offers sunset cruises, which we want to try next time!

All Male Sailing Tour: Snorkeling around the Blu Q Catamaran © Coupleofmen.com
All Male Sailing Tour: Nude snorkeling around the Blu Q catamaran © Coupleofmen.com

Tips for your All-Male Sail Adventure

Sunscreen 50+ is a must, as sun reflection and nude snorkeling increase the risk of sunburn. If you want to drink more than just chilled water, bring your own (alcoholic) drinks (ice and coolers are provided).

All Male Sailing Tour with Blu Q Group Photo © Coupleofmen.com
Special souvenir photo from the “All Male Sailing Tour” with Blu Q in Key West © Coupleofmen.com

Beach day under palm trees at Smathers Beach in Key West

Palm trees, sun, beach, and sea – the perfect image for many visitors to the Florida Keys. But did you know that all the sand and palm trees in Key West and the Florida Keys are cultivated artificially? The sand is imported from the Bahamas and other places. Nevertheless, one of our favorite beaches is Key West’s Smathers Beach in the southern part of the city. The fine sandy beach is lined with coconut palms for about 800 meters. This is an excellent opportunity for a souvenir photo!

Couple of Men Florida Keys Beach Key West © Coupleofmen.com
Couple of Men visiting the gay and LGBTQ+ friendly Florida Keys and Key West © Coupleofmen.com

Our Restaurant recommendations for Key West

For lovers of seafood and fresh fish, the Florida Keys is a gourmet paradise. Karl also had the opportunity to try the famous, mild, and sweet-tasting Key West Pink Shrimps. We recommend the quaint Half Shell Raw Bar. On the island of Sunset Key, off the city’s coast, is the famous Restaurant Latitudes, which can only be reached by boat shuttle. Although we missed the sunset, which is considered particularly beautiful from here (note: book well in advance!), we spent a pleasant, balmy evening under palm trees. With two vegan dishes, Daan could also enjoy a local culinary highlight.

Karl enjoying his fresh fish dish at Sunset Key Restaurant Latitudes © Coupleofmen.com
Karl enjoys his fresh fish dinner at Sunset Key restaurant Latitudes © Coupleofmen.com

We usually had breakfast at our resort. But on our third morning, we had a breakfast date with the mayor of Key West. Teri Johnston is the first openly lesbian and only the second woman ever to be elected mayor in Florida history. With fresh coffee, a vegetarian omelet for Daan, and delicious Eggs Benedict with lobster for Karl (our special tip), we sat in the morning sun at the Banana Cafe on Duval Street. Friendly, curious, and with a calm disposition – we listened with great interest to Teri’s stories about the history and LGBTQ+ friendliness of the city, her rainbow family, and the plans for an even queerer city.

Gay Florida Keys Breakfast in Key West with major Teri Johnston at Banana Cafe © Coupleofmen.com
Breakfast in Key West with Mayor Teri Johnston on the rooftop terrace of the Banana Café © Coupleofmen.com

Did you know that in 2003, LGBTIQ+ activists carried Gilbert Baker’s world’s longest rainbow flag through the streets of the island city at Key West Pride? Not only that, but it connected the Atlantic Ocean to the Gulf of Mexico, earning it the name the “Sea-to-Sea Rainbow Flag.” It is a truly inspiring and educational conversation about what it’s like to be LGBTQ+ or gay in Key West and the Florida Keys. We said goodbye with this beautiful selfie. Thank you for an exceptional breakfast!

Key West, the capital of the “Conch Republic”

Another special feature of Key West is the fact that the island town and some Florida Keys broke away from the rest of the USA and formed their republic, the “Conch Republic“. Flags and posters referring to this micronation were everywhere. Until now, the people of the Florida Keys hold on to the free ideas and flair of the past. In conversations, they rave about their personal reasons and happiness for calling Key West and the gay and LGBTQ+ friendly Florida Keys their home. As a gay couple traveling, we also felt the unique atmosphere of being different from the rest of the USA.

Evening Walk at our first night around the Key West Harbor by sunset © Coupleofmen.com
Strolling in Key West harbour on our first evening at sunset © Coupleofmen.com

Spectacular sunset in Key West at the end of our trip

The sun is a constant companion in the Florida Keys – from sunrise over the Atlantic to sunset over the Gulf of Mexico. A special place to end a sunny day in Key West is the Sunset Celebration in Mallory Square. Every day between 4.30 pm and 7.30 pm, tourists, dozens of street performers, local street vendors, and musicians gather in the public square to await the famous sunset.

Performances at Sunset Celebrations at Sunset Pier in Key West © Coupleofmen.com
Performances and live music at the Sunset Celebrations at Sunset Pier © Coupleofmen.com

We also let ourselves be swept away by the atmosphere before grabbing a little corner on the Sunset Pier. Here we had enough space to enjoy the sunset arm in arm. And as the sun slowly slipped behind the horizon, we managed to take some very romantic snapshots. Bye, bye Gay Florida Keys and see you next time!

Romantic Gay Couple Sunset Photo at Mallory Square © Coupleofmen.com
Romantic sunset photo at Mallory Square in Key West – Gay Florida Keys © Coupleofmen.com

Now it is time for your gay adventure in the Florida Keys and Key West

The time in Florida on the Florida Keys flew by. Sunshine, salt water on the skin, and varied activities accompanied by good food: The Florida Keys exemplify a sun-drenched and, at the same time, LGBTQ+ friendly holiday in the southeast of the USA. Our experiences were overwhelmingly positive: holding hands in public (even at night), sharing a kiss, or asking for a double bed when checking in at the hotel – we encountered no difficulties and enjoyed our gay adventure in the Florida Keys to the fullest.

Our tips for the Keys are meant to provide you with ideas and inspiration. We are unable to guarantee that this will be the case when you travel to Florida. Of course, we have researched carefully, and all experiences, opinions, and photos in this article are authentic.

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We would especially like to thank the Official Florida Keys Tourism Council, KLM Royal Dutch Airlines as well as the Island House in Key West for the invitation, the support, and the opportunity to experience the Keys in such a free and authentic way.

Would you like to learn more about us gay travel bloggers and experience our queer adventures together with us? Then stay tuned and follow us on Facebook, Twitter, YouTube, Pinterest, and Instagram! See you in Florida, the Florida Keys or on one of our next Gay Pride trips worldwide!

Karl & Daan.