Key West: A 20-Something Discovers the 'Conch Republic'

After a quick 20-minute flight from Miami I touch down amid swaying palm trees and a balmy early summer breeze. I am greeted by a sign that practically screams at me: 'Welcome to the Conch Republic.' I'm nervous that I've caught the wrong flight, but my tour guide, Stephen Murray-Smith, assures me that I am indeed in the correct location.

The name was coined by the locals after Key West (in tongue-in-cheek fashion) seceded from the Union in the early '80s. This is my first taste of Key West, and I'm already in love with its crazy charm and distinct local identity. It feels like nowhere else in the United States (technically, it isn't), and as Steve reminds me, I am closer to Cuba than the contiguous 48 states.

Clothing Optional: Equator Resort and Island House

After grabbing my luggage from an airport terminal smaller than my living room, I head to Equator Resort, which will be my home base for a long weekend. Equator Resort is one of the few remaining all-male, clothing-optional resorts on Key West, and as such, it offers a unique adult-only experience.

The staff at Equator greets me warmly, and shortly after checking in I hit the ground running and head to the world-renowned Island House Resort for drinks and to see what I might uncover. In a similar vein to Equator Resort, Island House is an exclusively gay male, clothing-optional environment, situated in lush surroundings and sheltered within a secure compound. The guests, in various states of undress, laugh and converse freely, and inhibitions are collectively cast aside. This sense of freedom is a cornerstone of the Island House experience.

I meet up with some other travel writers and after a couple of stops for further libations -- the liquor flows freely in Key West -- we dine at the Pier House Resort's Harbourview Caf, with Alex Velez, the Area Director of Sales and Marketing. Harbourview Caf, situated in an idyllic harbor overlooking the southern Atlantic Ocean, offers world-class and locally sourced seafood with a menu that caters to travellers with deep pockets.

Conversations with Alex reveal a number of interesting anecdotes about the island and its famed history as a gay mecca within the United States. After the colossal cultural shifts engendered by World War II, many closeted gay men fled to the island and made it their home. And in the age of Grindr and declining gay ghettos, Key West has managed to maintain its position as a gay epicenter, despite its location within socially conservative Florida.

Gay Nostalgia in the 21st Century

A night on the town following dinner supports Alex's assertions that Key West is one of the few remaining truly gay destinations. The guys and I find ourselves at Bourbon St. Pub, which hosts nightly performances by twinky go-go boys and offers lap dances for the (rather pricey?) sum of $25 a dance. Bourbon St. Pub also offers a male-only, clothing optional bar out back, with swimming pools, hot tubs and a 'maze', which, as we soon discovered, wasn't just a maze.

This is my first real experience observing cruising culture, and as a millennial that reached manhood in the Internet age, the situation feels almost like a throwback to the 1970s, when the public expression of sex was arguably a defining component of queer culture. Moving on to Saloon 1 at 801 Bourbon Bar we step in to a similar cruisy vibe with the night culminating in a "Biggest Dick Competition," with sub-categories including best balls and best foreskin... I'm not kidding. If you're looking for a raunchy night on the town, a sense of '70s gay nostalgia and a guaranteed hangover, then I promise you'll love both Bourbon St. Pub and Saloon 1 Bar.

Rum Tasting and Ghost Chasing

We all go kayaking the next morning while I nurse a hangover. As Steve aptly stated via text, "I'd had a little too much Key West." I'm back in good spirits after lunch and a mimosa, courtesy of Shore American Seafood Grill at the Hyatt Key West Resort. The restaurant offers some of the best views of the trip -- my eyes feast on crystal blue waters, adorned by golden sands and palm trees -- and the food, once again, is impeccable, specializing in seafood, traditional American fare and their famous fish tacos.

After lunch we spend some time at Key West's only rum distillery -- Key West Legal Rum and are treated to a tour hosted by the chief-distiller, Paul Menta, who meticulously describs the rum production process and its history. And of course, afterwards, there is rum tasting.

We finished our second day with a ghost hunt, led by David Sloan of Sloan's Ghost Hunt. The outing takes us all around the center of town at dusk to some of the island's most 'haunted' locations. Although somewhat absurd at times, the outing is mostly amusing and enjoyable, and I'll admit to being a little spooked on more than one occasion. Whether you're a sceptic or believer, the tour is worth the price for the history.

Sailing the Ocean Blue Q

The following day continues with a common theme of the trip -- socially permissible nudity... this time on the ocean. We board the Blue Q and spend four hours sailing around the southern Atlantic and Gulf of Mexico, stopping to snorkel and catch some rays. Only a handful of guests decide to strip down (my group not included), but the atmosphere, much like at Equator and Island House, is relaxed and devoid of judgment, with a big group of guys of all ages enjoying each other's company. Certainly, the Blue Q trip is a wonderful opportunity to make new friends in a relaxed environment, independent of the nightlife scene.

Safely back on land, we head to Jazz in the Garden at The Gardens Hotel. The resort is a celebrity hot-spot, and stars such as Michael Keaton, Justin Long, and Oprah are long-time fans of the first-class service and idyllic surroundings -- the pool area is stationed in a lush tropical garden, which serves as a home to a varied wildlife.

We concluded the evening with an Italian banquet at one of the island's finest eateries, Abbondanza Family Italian Restaurant. The menu is budget-friendly and the portions are more than generous. This is my favourite restaurant of the trip, and I highly recommend it for Italian food buffs.

Hemingway and Sunsets

On my last day I embark on a tour of Ernest Hemingway's house. The literary giant called the island home and his gorgeous property has been transformed into a museum dedicated to his work and memory. The house is well worth a visit if you're looking for an intellectual break from the go-go boys and dance music.

I spend the afternoon enjoying wine and making/tasting chocolate at Lush Bar, with wine and chocolate connoisseur, Mark Certonio. I soon learn that I am unable to make a half decent chocolate bar and as Mark emphasizes, an immeasurable amount of care and detail must go into the chocolate-making process. The day ends with a Wind and Wine Sunset Sail. A palpable highlight of the trip, it offers some exquisite views of the island at sunset.

As the sun sets over the small, yet vibrant island, I reflect on some of the core themes of the trip and reach the conclusion that this is a truly gay cultural destination that, in many ways, feels as though it has been preserved in time. Certainly, as much as I have entertained the notion of moving there permanently, a part of me feels as though Key West is perhaps a little too far removed from real life, and this is undoubtedly a drawback for some, as well being a huge appeal for others.

There is also something conspicuously exclusive about the island -- nothing is particularly cheap, and it seems to cater to tourists more than locals.

And yet, as a young, gay, 20-something, Key West is also an immensely exciting destination. The sense of freedom and erotic abandon is a novelty, perhaps less prevalent in larger cities in the north and west nowadays, and something that I am grateful to have experienced.

Key West Pride Week

If you are considering visiting this small piece of paradise, Pride Week could be an opportune time. Held from June 11th through the 15th, this year's event promises to be spectacular. My tour guide and friend, Stephen Murray Smith, explains what guests can look forward to during the world renowned Key West Pride Week:

"It is Pride month and time for you to step outside the box, leave the real world, and celebrate Pride on an island closer to Cuba than the United States. Spend your days on and under the water on one of our gay only or gay-welcoming boats and your evenings at poolside BBQ and splash parties, watching the sun set on a dinner cruise with live music, a tropical buffet and libations. Our bars will blow out the doors with special bar-top dancers, pride themed drag shows, and you can attend a one-of-a-kind disco wedding shower/dance party for Jeffrey and Bradley at the 801 Bourbon bar.

"Alexander's Guesthouse is throwing a special 'For the Girls' beach party at Higgs Beach by Salute Restaurant, while the Fury Ultimate Express invites men to board their Cruzan Cat power Catamaran for a clothing optional day parasailing, riding jet skis, kayaking, swimming, and playing on their giant water toys.

"On Sunday, Rob Smith, a decorated War Veteran who served 12 years in the army both in Kuwait and Iraq, is both an author, a public speaker, and LGBT activist headlines our Pride as the Grand Marshal. Our Pride parade is a colorful promenade starting at the Truman Annex and winding through Old Town and down the length of Duval Street. Elected officials both gay and allies of our community join the parade alongside guesthouse and bar floats, our Fantasy Fest King and Queen as well as other royalties, and a section of the Sea-to-Sea Rainbow Flag will be proudly carried for all to see."

Visit www.keywestpride.org for more information.