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Blue Flamingo Resort Key West
Blue Flamingo Resort Key West is best for travelers who want a relaxed, mixed gay/straight resort with pool parties and on-site dining. It's family-friendly and moderate price, with two restaurants and themed parties. The 24-hour open hours mean you can check in anytime. The property has a swimming pool and gym, but Yelp reviews average just 2.6/5, so keep expectations measured. There's no confirmed neighborhood detail, but the resort's layout is designed for outdoor seating and socializing.
Ernest Hemingway Home & Museum
Unlike typical writer's homes that feel like sterile archives, the Ernest Hemingway Home & Museum in Key West is lively with over forty polydactyl cats roaming the grounds. This museum in Old Town offers guided tours through rooms where Hemingway wrote some of his most famous works. The lush gardens and quirky cat residents give it a whimsical feel. It's open daily from 9am to 5pm. Regulars know mornings are quieter before crowds peak. You'll want to check the weather, as much of the tour is outdoors. If you're exploring queer arts in Key West, nearby Tropic Cinema often screens independent films with LGBTQ+ programming.
Carriage Trade House
The sign goes up when they're open, and until then you just have to wait. Carriage Trade House serves one meal a day, take it or leave it, and locals happily line up for it. This LGBTQ-owned Key West institution has been operating on its own schedule for years, making every visit an adventure. There's no phone, no website, and definitely no reservations. First come, first seated inside a tiny space that feels like a well-kept secret. If they're closed, try Blue Heaven nearby for a different Key West classic.
Key West Rainbow Crosswalk
Old Town's Duval Street corridor is home to the Key West Rainbow Crosswalk, installed in 2015. These four permanent rainbow crossings at Duval and Petronia mark the center of the city's LGBT entertainment district. The crosswalk is a colorful symbol of Key West's long history of supporting diversity. It's a free, accessible landmark you can visit any time.
"Off The Hook" Grill
In Old Town Key West, "Off The Hook" Grill is an LGBTQ-owned and women-led seafood spot with an oceanside setting. Its tagline 'Seafood and eye candy' hints at the vibe: great food and friendly service. Open seasonally, it serves American seafood platters and sandwiches during a limited schedule. The hours shift across the week: Mon, Tue, Thu, Fri 4pm-9pm; Sat and Sun 10am-9pm; closed Wed. Yelp notes suggest it may be permanently closed, so check before heading out. Regulars praise the happy hour and outdoor seating.
Tropic Cinema
This volunteer-run movie house is more than a place to catch the latest flick, it's a cultural hub of Key West. Tropic Cinema brings quality movies to people who long for something more than Hollywood blockbusters. Plus, the popcorn is absolutely delicious! Located in Old Town, it's a favorite among locals and visitors alike. Check their hours from 1pm to 11pm daily.
Cuban Coffee Queen
Cuban Coffee Queen is open daily from 6:30am to 7pm, making it an ideal stop for breakfast or an afternoon pick-me-up. This waterfront cafe in Old Town is famous for its eye-catching 'Key West' mural, a popular selfie backdrop, and serves up iced café con leche and 'Caliente Cuban Mix' sandwiches. It's a casual, trans-friendly spot that draws a mixed crowd. You'll want to grab your coffee to go and head to the beach, or sit outside and enjoy the view. The BIPOC-owned cafe is a local staple for a quick, affordable bite. For a longer meal nearby, consider Blue Heaven for a more leisurely brunch.
Truman Little White House
Crowds here are a mix of history buffs and curious travelers, drawn to the winter retreat of the 33rd president. Truman spent 175 days of his presidency at this Key West compound from 1946 to 1952. The house is preserved as a museum, offering a glimpse into his life and work. You'll find it on the Naval Air Station, adding a unique military backdrop. Guided tours run daily from 9:30am to 4:30pm. Upgrade to a 'white glove' VIP experience for a deeper look. Pair your visit with the Key West AIDS Memorial nearby to round out a day of local history.
Little Pearl
Little Pearl stands out in Key West's dining scene with a four-course prix fixe menu that changes with the seasons. The focus is on day-caught seafood and Asian-fusion flavors, served in an upscale yet relaxed setting. With a solid 4.4/5 rating on Yelp from over 440 reviews, it's a refined choice for a special night out. Reservations are essential given the fixed seatings from 5pm to 9pm nightly. The wine bar is a nice spot to start before settling in for your meal. For a more casual vibe nearby, you might check out Blue Heaven, but Little Pearl delivers a polished, intimate experience that's hard to beat.
Sandy's Café
The crowd at Sandy's Café is a mix of locals and visitors grabbing a quick bite. This family-run Cuban café has been serving Key West since 1984. Known for the Cuban Mix Sandwich, it's a budget-friendly spot with two walk-up windows. You'll find it at the crossroads of White and Virginia Streets in Old Town. The Santiago family keeps things casual and fast. Grab a sandwich and a Horchata to go. For a sit-down meal, nearby Santiago's Bodega offers a different vibe.
Berlin's Cocktail Bar & Lounge
Tucked behind A&B Lobster House in Old Town, this speakeasy-style cocktail bar has been a local retreat since the late 1940s. Plush leather chairs and jazz music set the tone for a classic martini lounge experience that feels a world away from Key West's busier streets. Berlin's opens nightly at 5pm with a casual, bar-food menu for those who want to eat while they drink. The crowd here skews local, making it a quieter alternative to Duval Street's party scene.
Parrot Key Hotel & Villas in Key West
Parrot Key Hotel & Villas sits along Key West's secluded northern shore, redesigned in 2018. It's a luxury hotel on the water, offering a pool and free shuttle to Smathers Beach. You're close to all the action without the chaos. The property is in New Town, away from the crowded Old Town. Regulars like the quiet location and easy shuttle service. It's a solid choice if you want a relaxing base with quick access to Key West's highlights. If you're looking for something more resort-oriented, consider Cheeca Lodge & Spa for its private beach and spa amenities.
Barbary Beach House Key West
Yelp reviewers give Barbary Beach House a 3.6 rating over 41 reviews. This pet-friendly hotel in Key West's New Town neighborhood offers a lagoon-style pool and easy access to Smathers Beach. Guests can dine at Drifter’s Cover Restaurant for fresh local seafood. The hotel operates 24 hours daily, so check-in is flexible. It's a solid choice for travelers who want a mix of pool time and beach proximity, all while bringing their furry friends along.
Red Shoe Island Bistro
Red Shoe Island Bistro serves up fresh Key West seafood with a European twist, drawing a mixed gay and straight crowd of locals and travelers in their 20s to 40s. It's a fast-casual spot with a lively vibe, tucked away in Bahama Village. Dinner runs 6pm to 9pm daily, so plan your evening accordingly. Yelp reviewers give it a stellar 4.8 out of 5, and the casual setting makes it easy to pop in with a group. You'll find a mix of 20-somethings through 40-somethings here, plus plenty of tourists mixing with locals. For a classic Key West experience, nearby Blue Heaven offers a different but equally beloved take on island dining.
The Green Pineapple
The Green Pineapple is an LGBTQ-owned women-led boutique on Duval Street that also houses a yoga studio and a plant-based cafe. It's a rare triple-threat space where you can shop for women's clothing and accessories, take a class, and grab a vegan bite all in one stop. Yelp data suggests the venue may be permanently closed, so call ahead before visiting. If it's open, regulars say the cafe's plant-based options are a quiet contrast to Duval's bustle. Head there mid-morning for a calm shopping or yoga session.
22&Co
22&Co is easily Key West's most inclusive, most glitter-filled LGBTQ+ bar, with a tutus-for-everyone policy. Decor reminiscent of unicorn vomit and creative martinis make for a fun night and great photos. The crowd skews 20-somethings and mixed, with women-led ownership. Open daily from 2pm (noon on weekends) until 2am on Duval Street. No cover confirmed.
Keys Coffee Co.
You might expect a coffee shop on Duval Street in Key West to cater mostly to tourists grabbing a quick caffeine fix. Keys Coffee Co. takes a different approach: it's women-led and roasts its own coffee, turning out a lineup that includes nitro cold brew and the local favorite iced coconut breve. The vibe is casual and unpretentious, more about quality than flash. They're open daily from 7am to 2pm, making it an ideal morning stop before the heat sets in. If you're in the mood for a bigger breakfast, you're a short walk from Blue Heaven, another local staple worth the wait.
Kojin Noodle Bar
On Duval Street, Kojin Noodle Bar serves noodles, ramen, and Asian fusion dishes. It has a 4.6 Yelp rating from 141 reviews. The space feels casual and welcoming.
Kojin Noodle Bar
Kojin Noodle Bar on Duval Street is known for its house ramen and dragon bowl, with a mural by local artist Jesse Carson. This casual cafe has a Yelp rating of 4.6 from 141 reviews. It's open daily from 11am, with Sunday starting at noon. A quick stop for noodles on your Key West visit.
Books & Books @ The Studios of Key West
Book lovers and Judy Blume fans will find a special spot in Books & Books @ The Studios of Key West. This nonprofit, independent bookstore was co-founded by Judy Blume and her husband George Cooper, a project born from a group of local bibliophiles. It's a casual, all-ages space with a budget-friendly price tag, reflecting a women-led, community-focused ethos. The shop sits on Duval Street, making it an easy stop while exploring Key West. As a locally-owned, independent bookseller, it offers a curated selection you won't find at chain stores. It's a place to browse, chat with staff, and support a good cause.
The Perry Hotel Key West
What sets The Perry Hotel Key West apart from other Key West hotels is its location on Stock Island, just one bridge from the historic Old Town. This waterfront oasis offers a genuine resort experience without the crowds of downtown. You can fish the backcountry, dive the Vandenberg, or lounge poolside. Homemade rum is available steps from your door. The hotel has outdoor seating and a swimming pool. It's a moderate-priced option in the $$$ bracket. For a change of scenery, nearby Gilbert's Resort offers another laid-back waterfront spot. This is a quiet escape for travelers who want to be close to Key West action without being in the middle of it.
Key West AIDS Memorial
One reviewer described the Key West AIDS Memorial as 'a beautiful and poignant spot,' with names etched into granite along the pier walkway. This outdoor tribute sits in a tropical setting near the ocean, offering a quiet place to reflect. The names of those lost to AIDS are inscribed on Zimbabwe granite slabs embedded in the path approaching White Street Pier. The site is free and open to all, blending remembrance with the natural beauty of Key West. It's a peaceful stop during a beach stroll, especially at sunset when the light hits the granite. The memorial is accessible 24/7, as it's part of the public walkway. For more local LGBTQ+ history, continue to the Key West Rainbow Crosswalk nearby.
Latitudes
The crowd at Latitudes leans toward well-dressed 20-somethings to 40-somethings, pairing a romantic upscale vibe with sunset views over the water. You'll find a fusion of American classics, fresh seafood, and tapas-style small plates, plus a Sunday brunch that draws a loyal local following. The outdoor seating is the main draw here; it's quiet and serene, with the gentle sound of waves. Reservations are recommended for dinner, especially if you want a prime sunset table. Check ratings and hours.
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