
CONTACTCAREER OPPORTUNITIESADVERTISE WITH USPRIVACY POLICYPRIVACY PREFERENCESTERMS OF USELEGAL NOTICE
© 2025 Pride Publishing Inc.
All Rights reserved
All Rights reserved
By continuing to use our site, you agree to our Privacy Policy and Terms of Use.
It wasn’t my finest moment. Exiting quaint Key West International Airport, I could still feel the pressure in my head. The sinus infection nearly derailed my trip to the island, but I managed to trundle myself into the plane and then to the taxi to take me to the Gates Hotel, Key West.
It wasn’t until I began to check in for the long weekend that I realized, I’d left my wallet on the plane. “Call immediately,” the man at the check-in desk advised, giving me the number. So I booked it my room to drop my bag and call my airline. “Yes, you’re in luck, we found it before the plane took off,” the agent informed me, but I needed to get to the airport.
Luckily, the Gates, one of the newest properties on the island, is located on the northwest corner, meaning as soon as you enter from the highway after the seven-mile bridge—or a few minutes from the airport. I quickly checked out a bicycle from the concierge and pedaled 10 minutes along the coast. I must say, if there’s one way to get through a prescription-drug stupor, it’s to feel the island breeze on a sunny spring day (although a plunge in the pool would have been just as welcome). After collecting my valuables at the terminal, I took a little more time to take in this corner of the island.
Each time I’ve visited Key West, it feels like it’s been a different era of my life. From childhood trips with my parents (during which I saw two men holding hands for the first time) to clothing-optional adult vacations with my partner and pals, I’ve come to appreciate how it can quickly change my mindset as I adapt to the dropout vibe of the Conch Republic. With the hotel located in New Town, this time I explored from a new side, with excursions into Old Town and meandering along Duval not the main focus. In fact, I never visited one of the great gay bars in the area, although the straight women on the trip did coax me into Aqua for the drag show for the first time—which if you've been you know is mostly packed with boozed-up bachelorette parties. But it was a great lesson learned: Key West continues to change and be whatever I need (or want) it to be.
The Rooms
The Gates has the feel of being an upscale motel, the fact that it's only two-stories and is easy to pull in from the highway, but put that thought out of your mind. The refurbish of the property is immaculate and classy, with attention to all design details. It's easy to fall into kitsch when in Key West, but the hotel manages to balance elegant touches without turning stuffy. For example the artwork found in the rooms and social spaces is all by Florida-based photographer and artist Jorge de la Torriente, which can be found at his De La Gallery in Old Town, and is a contemporary take on the typical blue skies, turquoise water, and palm trees you'll find in most sidewalk shops. I even spoke with a couple who had extended their stay because of the hotel's dog-friendly policy and amenities. So I guess it can easily be a home away from home. In fact, I was lucky enough to get one of the comfy robes, and oit's become a fave keepsake in my bathroom in New York.
Go by Bike
Bicycles make every trip better. It's a travel truism I've discovered over the past few years, so if there's a chance to hop on a bike, I take it. Luckily, the Gates offers city cruisers to rent. Of if you're feeling especially stylish (or are booked in The Scene room), you can also upgrade to one of Lorenzo Martone's colorful statements on two wheels (pictured above).
We took ours on a leisurely trip along the streets on our way to the female-fronted Lazy Dog for a two-hour paddle boarding eco tour. I'd never been on a paddleboard before but the instructions were simple and soon enough we were swiftly making our way through mangroves and searching out marine life. It was exciting for everyone when we saw a small nurse shark (don't worry, harmless) jet by, we tailed a manatee, spotted iguanas, and discovered starfish, sponges, octopus, and tropical fish in the sandy "back country." Afterward we hopped back on the bikes to ride another mile to the Hogfish Bar & Grill, an locals' fish shack that serves great bar food (try the signature fish sandwich), cold beer, and has plenty of seating with marina views. It was a great way to chill out far from the tourist crowds.
Drunk History
The hotel has partnered with Paul Menta of Key West First Legal Rum Distillery to feature a private-label selection of his spirits at its Rum Row bar. Visiting the first legal Key West rum distillery on the island (it opened in 2013 in a former Coca-Cola bottling plant) is another adventure not to pass up. Menta is a character who embodies that Key West feel: smart, friendly, and cool with anyone's quirks. I've been to a few distilleries this past year, but this one offers its own unique backstory, with strange paraphernalia dug up from Prohibition times, and the chef-distilled rum is made with Florida sugar cane. Bartender Robyn Whitehead has crafted a great list of cocktails using the rums, and I was blown away by the "Up in Smoke," which has tobacco on its rim. Make sure not to ingest the brown bits (it's for scent only), but it's a smokey flavor explosion you won't forget.
Chef's Table
The last few times I've visited Key West, I've been surprised to find that the restaurants are serving up incredible dishes with local seafood and fresh ingredients. It's not just conch fritters and mahi mahi sandwiches these days (although those are both fine when you're in the mood). But this trip I had my finest culinary experience, and it was at a place I probably would have never found on my own without someone holding my hand and making it all happen.
Isle Cook is a shop filled with kitchen essentials and gadgets, servicing locals looking for anything from artisinal cocktail mixers. But owners Bill and Eden Brown have gone one step further and set up a demo kitchen, and they offer tasting menus and wine education events from experts who are changing the way locals eat. Chef Michael Schultz prepared a meal that we might not find in any of the nearby restaurants but included some of his favorite imaginative surprises: an "edible Caribbean island" of coconut, blueberry and hearts of palm; a tasting of conch; and a local red grouper paired with plantain gnocchi and a pineapple mojo consommé. Skip the regular dining and options and find a time to graze here (or organize a special event)—you won't be disappointed.
Find out more about the Gates Hotel, Key West at its website.
From our Sponsors
Most Popular
Just in Time for Pride – The 15 Gayest Cities in the World in 2023
April 12 2023 6:47 PM
The 13 Least Visited National Parks
January 07 2023 5:00 AM
Get Soaked! with These 35+ Steamy Pool Pics From This Year’s White Party
May 25 2023 9:29 AM
20 Thirsty Pics of #SniffiesRush Campaign Celebrating Frat Life
December 16 2022 3:19 PM
25 Thirsty Pool Party Pics from White Party Palm Springs 2022
April 14 2023 5:55 PM
Sniffies Reveals Horniest Cities
December 22 2022 4:15 PM
15 Thirsty Pics of Moot Lingerie for Men
March 21 2023 7:41 AM
The 7 Best Nude Beaches for Gays in the U.S.
June 09 2022 4:00 AM
The Most Dangerous (& Safest) Countries for LGBTQ+ Travel
March 22 2023 5:00 AM
Outtraveler: Featured Video
Latest Stories
When love sinks, set sail for the Hudson Navigator
August 15 2025 6:00 AM
Top 10 LGBTQ+ beach towns perfect for Pride and summer fun
June 05 2025 1:54 PM
Gays went feral at an iconic Pride celebration in Pensacola, Florida
May 30 2025 6:00 AM
Out and About with Christian Cooper
May 28 2025 11:07 AM
Small-town charm to big city Pride: exploring LGBTQ+ Ontario
May 07 2025 5:00 AM
'Boys! Boys! Boys!' debuts new podcast
May 01 2025 5:03 PM
Need an escape from American anxiety? Consider Colombia.
July 16 2025 11:47 AM
Checking out: nhow London, the city’s coolest hotel
June 02 2025 8:45 AM
Wilderness, woods, and Wigstock: Drag icons light up the Catskills
May 28 2025 12:17 PM
A Night Out in San Diego: A queer couple’s moonlit travel guide
May 19 2025 12:00 PM
Weekend of pride in Charlotte, N.C.: The ultimate LGBTQ+ guide 2025
May 19 2025 10:25 AM
Asheville, N.C.: where standing out means fitting right in
May 15 2025 9:00 AM
This heavenly hotel in the heart of Hell's Kitchen is the perfect oasis
June 26 2025 6:00 AM
Cruising the world helped this gay couple find lasting love
May 31 2025 2:45 PM
A Day Out in San Diego: A queer couple’s breathtaking travel guide
May 19 2025 12:00 PM
Lesbian Pride: Here's every Dyke March in the U.S. in 2025
May 14 2025 7:44 AM