Five things we love about Key West that keep us coming back again and again

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If you’ve yet to have discovered the balmy, eclectic charm of Key West, add it now to your list of places to visit. If you already have, get back there ASAP.

At the southernmost tip of the Florida Keys, the very end of Route 1, Key West offers a truly laid-back, live-and-let-live atmosphere, where little will raise an eyebrow: People are too busy getting the most out of life, enjoying the sunshine, or mixing their next Margarita.

This LGBTQ hotspot offers a blissful and carefree getaway quite unlike anywhere else in the U.S., with plenty of outdoor attractions for breathing space and totally safe experiences communing with sun and sea that you really can’t get anywhere else in the world.

Here are just five reasons why we love it so much.

The beaches

Key West is 4 miles by 2 miles in size, so you never have to go far to enjoy some sand and surf. LGBTQ visitors tend to favor the palm-fringed Higgs Beach in the Old Town district. Catch some rays from a rented chair on the shoreline or stretch out on the old wooden pier. Not far from Higgs is Fort Zachary Taylor State Park, near the southernmost point of the key. Besides the beach, you’ll also find nature trails and the ruins of a historic fort to explore.

Smathers Beach, located near the small Key West airport, is the largest in Key West and is popular for its super-soft sand.

All the beaches will delight water-lovers. The Florida Keys were formerly coral reefs, and snorkeling along the shore can bring you up close to snapper, parrotfish, lobster, and turtles. If you want to try kayaking, paddle boarding, parasailing, or jet skiing, the beaches and calm, crystal-blue waters of Key West will not disappoint.

If you prefer to kick back and let someone else do the work, you can book a trip on a glass-bottomed boat to explore the reefs, go dolphin-watching, or fishing.

The guesthouses

Key West offers a fabulous array of accommodations, with a unique number of friendly guesthouses where the experience is much more like home away from home than an impersonal hotel brand. Resorts such as the clothing-optional Island House are famed by gay travelers from across the globe, while others flock to the gay-friendly, historic, wood-clad La Te Da Hotel (home to a busy Sunday Tea Dance in normal times), the historic Alexander’s Guesthouse, the Equator Resort, or New Orleans House, which is on Duval Street. All are based in the Old Town part of the city and offer a friendly, personalized welcome.

They all offer pools, hot tubs, and the chance to mingle with guests over evening cocktails and other activities. In fact, we’d say the opportunities for vacation romance are one of the reasons people return to these resorts again and again.

If you prefer bigger hotels, you’ve got those too, with the likes of the Hyatt Key West Resort and Spa or stunning Casa Marina Resort & Beach Club. If traveling with kids, the Havana Cabana at Key West is regarded as one of the best for families.

Want to stay somewhere new? Kimpton Key West is a collection of Old Town boutique-style cottages. Its 44-room Fitch Lodge, 45-room Lighthouse Hotel, and 85-room Winslow’s Bungalows have recently opened. These will be joined in 2021 by Ridley House (the former Cypress House Inn) on February 14, which the brand says will be perfect for, “honeymooners and VIPs.”

Another new opening due in early 2021 is the boutique Capitana Key West, on North Roosevelt Boulevard, close to downtown Duval Street. It will offer a private beach overlooking the Gulf of Mexico.

The pools

Island House (Photo: David Hudson)

Although you have the ocean on your doorstep, many prefer to idle away their time beside the hotel pool. Men’s resort Island House claims to offer the biggest guesthouse pool on the island, with plenty of decking and a private sundeck. There’s even a misting system to ensure cool comfort during the gloriously hot months.

Gay-friendly Equator Resort offers two pools and two hot tubs, with a complimentary happy hour from 5pm to 6.30pm and free, morning yoga. For more strenuous activity, the net across the pool at the all-male New Orleans House has been the scene of plenty of friendly volleyball rivalries.

If you like your resorts big and luxurious, then the Southernmost Beach Resort is an upmarket, family-friendly destination with three pools: A large, ‘Shores’ pool beside the ocean, a smaller adults-only ‘Tranquility Pool’ surrounded by swaying palms, and the smaller ‘Pineapple Pool,’ which offers live music twice a week.

The aforementioned Casa Marina Resort, part of the Waldorf Astoria Group, offers two beautiful, family-friendly tropical pools where you can swim lengths, or enjoy the opportunity to book a poolside massage.

The dining

You’re guaranteed two things from dining out in Key West: great seafood and Cuban-inspired cuisine (Cuba lies only 90 miles south). El Meson de Pepe is an authentic Cuban hotspot, and it’s located on Mallory Square in the Old Town area: a prime sunset-watching location.

Sample conch fritters, coconut shrimp, and lobster pizza at the Seaside Cafe at Mansion, or feast upon the surf’ n ’turf at Prime Steakhouse. For the freshest crab, head to the appropriately named Stoned Crab, next to Ibis Bay Beach Resort in New Town. It has its own fishing boats to deliver fresh catch direct to the kitchen.

Key West offers dining options to suit all tastes and budgets. For a cheaper eat, a must-visit is Harpoon Harry’s (832 Caroline Street), which offers an old-fashioned, American diner vibe and is popular for breakfast with many of those staying at the gay guesthouses. Another breakfast option is Date & Thyme (829 Fleming Street): a natural foods market and cafe that offers acai bowls and smoothies to help fuel your day.

(Photo: Kermit’s Key Lime Pie Shoppe)

And for dessert? What else but some tangy Key Lime Pie. You can buy this at almost every restaurant in the city. Kermit’s Key Lime Pie Shoppe is another iconic, local stop-off point: its frozen, chocolate-dipped Key Lime Pie will satisfy the sweetest of teeth. You’ll find the original location at 200 Elizabeth Street, a short walk from Mallory Square, with a second outlet on the corner of Front and Duval.

The bars and cafés

Bobby’s Monkey Bar (Photo: Supplied)

You’ll find a vibrant bar scene along Duval Street. Because of COVID, it’s currently operating at a reduced capacity and requires mask wearing when not seated. Long-running gay favorites include 801 Bourbon Bar (801 Duvall Street), with its regular karaoke, drag and bingo nights, and the local-friendly, dive-ish Bobby’s Monkey Bar (900 Simonton Street). It has karaoke every night but is currently ensuring people wear masks when singing.

Next door to 801 you’ll find cruisy fun at leather club Saloon1, while Aqua (711 Duval) offers more drag cabaret and dance tunes in a club setting. The biggest late-night destination is probably Bourbon Street Pub (724 Duval), with its army of go-gos and men-only garden bar with outdoor pool and jacuzzi.

If you want to just enjoy a coffee and some people watching during the day, check out Keys Coffee Co., in the old town district at 505 Southard Street. It takes its roasting very seriously, and besides the expected hot drinks, offers nitro cold brew and an amazing iced coconut breve to take away.

There’s also the iconic, waterfront Cuban Coffee Queen (284 Margaret Street), famed just as much for its eye-catching ‘Key West’ mural that absolutely everyone uses as a background for selfies. It’s the perfect place to grab an iced Café con Leche and Caliente Cuban Mix sandwich (roasted Mojo pork with ham, pepper jack cheese, horseradish mayo and jalapenos), before heading to the beach.

Other Cuban Coffee Queen locations can be found at Southard and Duval, and Clinton Square Market.