Here’s Your Checklist for a Fun Key West Getaway

Here’s Your Checklist for a Fun Key West Getaway

In Key West, they salt margaritas, not sidewalks.

~ Zë

While Key West is known for being one of the most queer-friendly cities for nightlife, entertainment, and cuisine in the US, there are also plenty of opportunities for enjoying some romantic downtime with your significant other. 

Whether you’re on your honeymoon, celebrating an anniversary, or just need some days away with your honey, this checklist has all you need to plan your next getaway to the Conch Republic.

Where to stay

Alexander’s Guest House. Photo: Nick Doll Photography

From resorts to hotels to guesthouses, romantic-ready accommodations are abundant in Key West. Choose from one of the following for some sweet R&R.

  • Silver Palms Inn: If you ever had the pleasure of booking a room at the lesbian-owned and -operated Pearl’s Guesthouse in its heyday, you’ll be pleased with a stay at the Silver Palms Inn, run by former Pearl’s manager Mey Espinoza. Enjoy the tropical vibes in the delightful guestrooms (or outside by the pool), and make sure to rent one of their colorful bikes to aid in your Key West exploration.
  • Alexander’s Guesthouse: One of the most LGBTQ+ friendly lodgings in Key West (and annual host hotel for WomenFest), Alexander’s Guesthouse is a quiet little oasis you’ll love making memories in. This 21+, conch-style home features a relaxing pool, Jacuzzi, lending library, and two clothing-optional sundecks because, hey, vacation!
  • Pier House Resort & Spa: Impress your beloved with a room or suite at this luxury resort. It’s got everything you need for a romantic getaway, from a private beach to a poolside bar, an entertainment center, multiple onsite restaurants, and, of course, The Spa at Pier House where you can both get pampered with a slew of signature treatments.
  • Kimpton Key West: For a deliciously relaxed vibe, check into the Kimpton Key West. Try a room at the boutique, adults-only Ridley House, or opt for one of the more private Winslow Bungalows, and make sure to enjoy the amenities including pools, bikes, and yoga mats — all included.

Starting your mornings right

Photo: Farknot Architect/Shutterstock

Whether it’s a coffee, smoothie, or snack (or all of the above — we won’t judge), you’ll want some sustenance to fuel your Key West adventures. Here’s where to find it.

  • The Koffie House: Located inside one of the oldest brick houses in Key West, this health-conscious coffee shop offers a vegetarian and vegan-friendly food menu alongside coffee and espresso drinks, cold-pressed juices, teas, and smoothies.
  • Cuban Coffee Queen: This quirky Cuban cafe has three locations: a walk-up on the waterfront for couples on the go, one at the Clinton Square Market, and a newer location near Duval Street with a dine-in option. All serve breakfast and lunch as well as Cuban-inspired snacks, energizing café con leche, and other Cuban coffee drinks, smoothies, and more.

Outdoor adventures

Photo: Varina C/Shutterstock

With so many things to do in the great outdoors, those fresh sea breezes will start to feel like your second skin in Key West. Get your heart pumping on, under, and even above the water, or just kick back and relax while sightseeing.

  • Sunset Watersports: Experience everything Key West’s outdoors has to offer with Sunset Watersports. Book a tour of the Florida Keys National Marine Sanctuary by jet ski, snorkel North America’s only living coral barrier reef, soar to new heights by parasail, or kayak your way through mangroves — and leave with lasting memories.
  • Key West Conch Train: For something more low-key, hop aboard the charming Key West Conch Train. Operating since 1985, this world-famous train takes guests on a 75-minute tour of Old Key West with multiple stops along the way — a great option for seeing the island without too much walking.
  • Dry Tortugas National Park: Impress your significant other with an all-day adventure at Dry Tortugas National Park. Explore historic Fort Jefferson; enjoy snorkeling to view coral reefs, fish, and other sea animals; go bird watching; or just spend time on the beach. Getting there is an adventure in itself — the park is only accessible by boat or seaplane.

Indoor entertainment

Photo: Mike Freas/Florida Keys News Bureau

If you need a respite from the heat or happen to hit a rain day, take it inside and get some culture while you’re at it. 

  • Tropic Cinema: This Art Deco-inspired theater shows indie, classic, and international films. Check their calendar while you’re in town for info on special events, including talks with directors, concerts, and more.
  • Key West Butterfly & Nature Conservatory: There’s a bit of magic in being in a room filled with hundreds of delicate butterflies hovering and swooping all around you. Enjoy the quiet calm of this small conservatory together, where you’ll also see colorful birds and an array of flowering plants.
  • Tennessee Williams Museum: Tennessee Williams (of A Streetcar Named Desire fame) made Key West his home for over 30 years. Stop in and learn more about one of the first openly gay American playwrights at this museum housing first-edition plays, photographs, and other artifacts.
  • Peruse (and potentially purchase) local art: Key West is a haven for artists of all kinds. Pop into one of the many local galleries, including Art on Duval, 7 Artists & Friends, and The Studios of Key West, for the chance to snag some original souvenir art.

Savoring a romantic sunset

Photo: Bob Krist/Florida Keys News Bureau

Visitors come from all over to catch the Key West sunset. Here are the best ways to do it.

  • Venus Charters: If you’re interested in stepping off the main island, hop aboard a Venus Charters private sunset cruise. This lesbian-owned charter boat company will take you and your significant other out to sea for one truly unforgettable sunset. Pack a picnic and something bubbly to toast with!
  • Mallory Square’s Sunset Celebration: For first-timers in Key West, Mallory Square’s Sunset Celebration is a must. This daily event features live music, entertainment (think high-wire acts, jugglers, etc.), food and vendors, and unobstructed views of the sun sinking into the Gulf.
  • Fort Zachary Taylor Historic Park: The southernmost state park in the continental US is home to a well-preserved pre-Civil War fort, hiking and biking trails, and a nice stretch of beach from which to quietly take in the sunset. It’s a great alternative for those who’d rather end the day with their toes in the sand.

Ending the night right

Photo: Mike Freas/Florida Keys News Bureau

After a full day of exciting adventures inside or out, it’s time to put that cherry on top and enjoy the Key West nightlife.

  • Dinner at Latitudes: If you’re after a romantic evening overlooking the sea, book a table at award-winning Latitudes. This elegant restaurant is open for breakfast, lunch, or dinner, but it truly sparkles at sunset and beyond.
  • Better Than Sex Dessert Restaurant: For a sweet way to end your evening, pop into this intimate, dessert-centered spot. Get close at your private table and enjoy treats with risqué monikers (Kinky-er Cream Pie, anyone?) alongside wine, beer, or cocktails to wind down for the night.
  • LaTeDa Cabaret: If you’re not ready for the night to end, catch a lively show at the ever-popular LaTeDa Cabaret. Pop in for a nightcap at the piano bar, or book tickets in advance for the best drag cabaret in the Keys — either way, you can’t go wrong!

Now that we’ve whet your appetite for Key West romance, it’s time to plan your getaway. 

This post is proudly produced in partnership with the Monroe County Tourist Development Council.