Why Key West Needs to be in Your 2020 Travel Itinerary

I think it’s safe to say that most of us would love to spend the new year in some type of tropical destination that caters fully to gay men! At the southernmost point in the United States sits an island perfect for a quick vacation getaway with a big hint of gay! Key West is littered with tourists who drive down the scenic highway from Miami or those who jump off a cruise ship docked in port, but a growing number of those visitors are LGBTQ. One of those visitors was yours truly! I took a four-day vacation to sunny Key West to see just what all the talk was about.
After landing and a quick taxi ride into town, I got dropped off at Island House, a clothing-optional resort nestled away in the lush greenery of the island. The faint sounds of a rooster in the distance signaled I wasn’t in Atlanta anymore. As I entered the facilities, I was greeted promptly and immediately felt right at home. There’s something magical about a space where gay men can unapologetically be with other gay men. I mean, fully nude with raging hard-ons and no one bats an eyelash. It’s almost a rite of passage when you visit a clothing-optional gay resort. There are plenty around the country, from west to east coast. Since 1976, The Island House has offered a getaway for gay men of all ages to strip down into their most comfortable clothing without fear of ridicule. It’s not the only gay clothing-optional resort on the island. Equator Resort also gives visitors a chance to mingle with other gay men. I’ve stayed at both and can say each has its own unique experience.
On this trip, I’m meant to write about my adventures in hopes that others reading this article will make the move and travel down to Key West. I don’t think I need to do much convincing especially when it comes to visiting this tropical destination. The gay men flock here by the boatloads and even the bike loads, as the previous weekend before I arrived was a huge bike race from Miami to Key West. A few men from Fort Lauderdale staying here made small talk with me, welcoming me with their open arms and manhood. The resort boasts two hot tubs (one indoors), sauna, steam room, small gym, full bar, 24-hour restaurant, a dark room play area, and enough housing to make this place a busy destination year-round.
Peak season starts right after the Thanksgiving holiday and goes until late-March, but locals I talked to say it’s pretty busy all year! Restaurants like the Hot Tin Roof were a must-stop on my trip. One, because of the absolutely delicious food and two, the extremely attractive wait staff! Restaurant manager, Mark Englehart doesn’t consider this a gay restaurant but his staff does a great job welcoming in the diversity. He’s lived in Key West for 20 years, managing the Hot Tin Roof for nearly 12 years.
“You have a safe, friendly community here. You can be gay, hold hands here and not be harassed. There is a sense of acceptance here which is what I would say is a pro here,” he said to me. “Our staff is all very good looking men, so that’s a bonus here plus the delicious food. Our attitude here is very pro-Gay.”
The restaurant overlooks the water where boat watching is a prime part of the dining experience. One of those boats you might catch a glimpse of is called the Blu Q Catamaran. I wasn’t able to take the excursion on this trip but have been on a previous trip to the island. It’s an all-Gay excursion with a ship-boy who prepares a meal with champagne while the catamaran sails into the shallow crystal blue waters surrounding the island. We went snorkeling and kayaking all before heading back to Key West with the breeze in our hair. It’s a must-do when you visit the island and a perfect way to make new friends.
The gay nightlife in Key West offers bars, clubs, drag-shows and a female-impersonator singer like you’ve never seen before. The first sentence in his bio on his website says this, “Christopher Peterson is a master of impersonations, both visually and vocally, and his comic timing is impeccable.” I’ve now seen him myself and I can say he’s visually, vocally, and comically stunning!

A friend I made at the Island House joined me for the evening show after dinner downstairs at the very gay LaTeDa restaurant. We sat in front with a key lime pie martini in hand and a packed house behind us. Christoper sang all of the greats: Cher, Bette Midler, Judy Garland, Barbra Streisand, and Liza Minnelli all while adding in whimsical banter from his childhood and beyond.
Down the street from LaTeDa sits the center of gay Key West, the Bourbon Street Pub. It’s a New Orleans-themed video bar featuring go-go dancers, live DJs, five bars, and a ‘male-only’ clothing optional garden bar with a pool and jacuzzi. A few doors down sits Aqua Bar and Nightclub, known for its iconic drag shows downstairs and high-intensity dance parties upstairs.
That’s a lot for one night in Key West which is why I recommend taking an extended vacation to experience all the island has to offer! Greg Troba, Key West’s LGBTQ representative has called the island home for years and says it’s a perfect place for a quick getaway.
“I wanted a place where I could walk or bike, year-round warm weather, and an LGBTQ community,” he told me as we dined underneath the stars at LaTeDa. “And it’s incredibly laidback. There’s not a lot of this gay or straight, everything is mixed and everyone mingles together!”
He’s seen the island evolve, but knows it’s never lost its gay edge. He compares it to destinations like Palm Springs, California, and Provincetown, Massachusetts. And if you’re looking for a quick New Years’ getaway, there’s one thing that Key West offers that you don’t want to miss come midnight on New Year’s Eve: a big red high heel!
Thousands of people flock to Key West for the 22-year tradition which involves a red fiberglass high heel measuring 8-feet-long with a 4-foot high heel. Created by Joseph Schroeder who opened Bourbon Street Pub 23 years ago, the tradition packs out all corners of Duval Street with a mixture of gay and straight visitors and locals.
You can find families with kids straddling the streets next to rowdy bachelorettes, leather daddies, drag queens and every other walk of life you can imagine in this inclusive island tradition of celebration, according to South Florida Gay News. For many gay locals, that’s the definition of what Key West is and it’s why Key West should be on your list of destinations in 2020! I recommend and I approve!