The Gates of Key West

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 to nifty cooking utensils. 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 consomme. 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.