Quit your job and move to Key West!

At least, that’s the advice of Key West residents David L. Sloan and Christopher Shultz in their iconic book of the same name. Many have followed that advice and it’s easy to see why. Key West and the Florida Keys are a bona fide subtropical gaytopia.

The archipelago reaches its sturdy arm out into the Florida Straits to the furthest point of the US – closer to Cuba than Florida. Its residents – and visitors – are treated to Caribbean climates all year round. Tropical oceans perfect for water sports surround the keys – as do pristine beaches and coral reefs, brimming with sea life every bit as colorful as the islands themselves.

Over the centuries Key West and the Florida Keys have been the port of pirates, famous sailors and later the home of inspirational writers like Ernest Hemmingway. Nowadays, the tranquil setting has nurtured a chilled-out “live and let live” approach to life in its inhabitants. Not to mention a flourishing gay scene away from pesky mainland politics.

There’s no need to go to such extremes as quitting your job though. Our advice would be more like: ‘take a vacation and go on a four-day road trip through the Keys’. And that’s exactly what we did. Learn about our adventures, so you too can follow in our footsteps – or rather car tracks – through Key West and the Florida Keys.   

Key West

Cruising into Key West’s airport on our – alarmingly small – aircraft from the mainland, we were treated to a stunning view of the entire archipelago. Key West sits at the far end of the keys and is one of the oldest cities in the US. It’s also a real visual delight – characterized by its garishly colorful buildings, palm tree lined streets and towering gingerbread mansions.

Where We Stayed

After disembarking, we began our Keys adventure by booking into gay guesthouse Island House Key West for two days. Opening in 1976, Island House was one of the first gay guesthouses in the world. Its thirty-nine rooms were redesigned to perfection in 1999 and are now a study in luxury and comfort. There are large comfy beds, queer art decorating the walls, mood light settings on the mirrors, ceiling fans, light up headboards and snazzy shade control blinds. The resort has a café, a pool with parties every Wednesday and Sunday, a clothing-optional sundeck and a bar with smoking hot bartenders – who definitely know how to handle a good cocktail or two.

What We Did

With our base of action all set, we headed out to explore Key West. The Conch Tour Train is one of the best ways to get the rundown of the main sights of the city. Running twice an hour, it gives a seventy-five-minute sightseeing tour throughout the town, setting you on the right path to where all the key – see what we did there – museums, attractions and historical buildings are.

Another good way to see the city is to – like us – book a bike tour with Key Lime Bike Tours. This was our first time doing a bike tour and we absolutely loved it. By bike you can see the Hemingway House, Mallory Square, the Southernmost Point, Key West Cemetery, the Key Lime Pie Factory and the Key West Lighthouse…to name but a few. The latter being famous for having the first woman lighthouse keeper – talk about breaking the glass ceiling.

As far as museums go, Key West has a lot to offer, from the Shipwreck Treasure Museum to the Ernest Hemmingway House and Museum. The Hemingway Museum is especially a must see. Keep an eye out for the six-toed cats, which are descended from a feline Hemmingway was gifted with by a passing sea captain.

On our first evening we took a trip out to sea on the Land’s End Sunset Sail with Sebago Key West. It’s a relaxing – if a little overcrowded – boating experience with amazing sunset views over the Keys, good food, live music and – most importantly – free flowing drinks.

Where We Ate

Throughout our two days, we ate like pirate kings. Key West has a vibrant food scene with many restaurants to choose between serving fresh seafood, Cuban cuisine, and other international dishes. Conch fritters, key lime pie, and Cuban sandwiches are among the local specialties. One of our favorite eateries was Nine One Five – actually a hotel, bar and restaurant with a British colonial motif split over three buildings. We recommend trying the Devils (bacon wrapped dates), Ahi tuna gravlax, soul mama seafood soup, lobster ravioli and whole yellowtail snapper.

We gleefully devoured meals at a number of other restaurants too – including the nautically themed Boat House at Turtle Kralls (try the mahi mahi sandwich), Half Shell Raw Bar (try the conch fritters and baked oysters samplers), Italian Food Company (try the octopus, woodfire oven-cooked margherita pizza and grilled lamb chops) and Blue Heaven (for a laidback outdoor breakfast surrounded by lush trees).

Where We Drank

As the sun set, we dived headfirst into Key West’s nightlife which is – in a word – vivacious. Most of it centered around Duval Street, where a beautiful plethora of rainbow flags mark the gay bars and clubs. There’s no shortage of gay bars to choose between but we took a personal liking to 801 Bourbon Street Pub for its fun atmosphere, drag shows and karaoke.

The drag queens never seem to sleep in Key West and we also attended a drag cabaret show at Aqua Night Club, where there’s a show and club night every night of the week. Yes, every night.

The Florida Keys

Moving back up the Keys we reached our next base of action, Islamorada – which sounds like the name of a Disney Princess and took us a while to learn how to pronounce (the “s” is silent).

Where We Stayed

Amara Cay Resort is THE place to stay in Islamorada. This little slice of paradise sits right up on the shore and has one hundred and ten suites, boasting some of the best views on the island. We went for an ocean view in our room – even though we suffered the horrific injustice of some of the ocean being blocked by the coast’s gorgeous pine trees. The outdoor spaces around the resort are huge, including a gorgeous pool area – and run right up to the shore. The resort is also a great launching point for water sports like snorkeling, scuba diving, jet skiing and kayaking – which we had a good go at. 

What We Did

A highlight of the area was our trip by car to the Turtle Hospital, a sanctuary for sick and wounded turtles. There were about thirty-six turtles there when we went, some in permanent residence and others to be reintroduced to the wild – including two rather cute baby turtles.

On the topic of cuteness, it’s worth taking a drive around the Big Pine Key area to see the famous Key deer that inhabit the area. These tiny deer are about the size of small dogs and are best seen in either the early mornings or evenings.

Where We Ate

We continued to eat like pirate royalty in Islamorada with many restaurants within easy distance with the resort’s free shuttle service. Our personal favorites being Chef Michales (where we munched on the petite Lionfish “Creole”, Roast Duck and Yellowtail Snapper with Juliette preparation) and the naughtily named Bad Boy Burrito, where the Cayo Hueso and Chicken Chipotle tacos went down easily.

Where We Drank

For nightlife, nothing beats the chilled vibes and craft beers of the Florida Keys Brewing Co. The beer is sold all over Florida, but it is in the keys where it first opened – starting with a home brew kit the owner got for Christmas. Since then, they’ve made around a hundred beers over their nine years in business. All their brewing is done on site, ‘jala-mango’ being their most popular beer. We recommend the lighthouse lager for a typical beer (which donates $1 to fixing up the local lighthouse), jala-mango for a spicy kick or – Auston’s personal favorite – the hurricane Irish red. Whatever you choose, kick back and enjoy in their beautiful beer garden with live music as the sun sets over the Keys.

Key West and the Florida Keys left us with a great taste in our mouths – both literally and figuratively. It’s hard to shake the feeling that, as LGBTQ+ folk, Key West is the place we’d like the world to be with that chilled-out “live and let live” approach to life. As such, we might not be moving there to live, but we will certainly be bringing a piece of it back with us in our hearts…and most assuredly in our stomachs.

This article was sponsored by the Florida Keys & Key West.