Thirsty Mermaid
Cozy raw bar and wine spot with super-fresh seafood, creative small plates, and a relaxed neighborhood feel.
Square Grouper
Laid-back local favorite for fresh fish, island flavors, and creative daily specials, with a relaxed vibe that feels more like a neighborhood hangout than a tourist spot.
Island Restaurants
La Trattoria
Classic Italian on Duval with house-made pastas, great wine, and a warm, romantic atmosphere.
Louie's Backyard
Iconic oceanfront fine-dining spot in a historic Victorian home, known for creative Caribbean-inspired cuisine, sunset views over the water, and a romantic, tucked-away back deck.
Seaside Cafe at The Mansion
Beachfront café and bar set on the lawn of the historic Mansion, famous for its lobster pizza, craft cocktails, and laid-back, toes-in-the-sand vibe just steps from the water.
Saluté
Beachfront favorite for sunset views, toes-in-the-sand dining, and classic Key West comfort food.
Smathers Beach
The island's largest public beach, famous for its soft white sand and vibrant water sports scene.
Fort Zachary Taylor
A local favorite known for its natural shoreline and perfectly clear waters ideal for snorkeling.
Key West Beaches
From the hidden coves of Fort Zachary Taylor to the sparkling activities at Smathers Beach, explore the most breathtaking shorelines Key West has to offer. Find your perfect spot for sun-drenched relaxation.
Higgs Beach
Offering tropical charm with a historic wooden pier and plenty of shade under the palm trees.
Simonton Beach
The only downtown beach, perfect for watching boats return to the harbor at sunset.
Cocktail Lounge
General Horseplay & Highnote
A refined haven for spirits connoisseurs, offering artisanal cocktails inspired by Key West’s prohibition-era history.
Cocktail Lounge
Berlin's
An elegant hideaway above the historic A&B Marina, Berlin’s pairs harbor views with craft cocktails, fine wines, and a refined, grown‑up atmosphere—ideal for a quiet nightcap or a special-occasion drink after dinner.
Uncover Key West’s most iconic evening haunts, from refined cocktail lounges to legendary live music venues.
Bars & Nightlife
LIVE MUSIC
The Green Parrot
Step into history where Hemingway once sat. Legendary live performances and an energetic spirit that defines Key West nightlife.
MARTINI BAR
Virgilios
Tucked just off Duval, Virgilios is an intimate martini bar with live music, candlelit tables, and a long list of handcrafted cocktails—perfect for a polished yet laid‑back Key West night out.
Live Music
A monthly stay in Key West offers the perfect rhythm to discover the island’s most iconic stages and intimate live performances.
FEATURED VENUE
Key West Theater
Experience world-class artists in this intimate, historic setting. A perfectly walkable downtown location for our guests, it offers a refined acoustic experience in the heart of the island.
OUTDOOR SERIES
Coffee Butler Amphitheater
Enjoy open-air waterfront shows featuring big-name acts and unparalleled sunset vibes. This premier outdoor venue captures the true spirit of Key West island life.
Fishing Charter
Embark on an elite angling journey through the storied backwaters and deep blue horizons of the Florida Keys. From trophy catches to serene flats, experience the ultimate maritime adventure curated for the discerning sportsman.
Boat Days
Sandbar & Snorkel
Escape to hidden sandbars and vibrant coral reefs for a day of pure island immersion. Dive into crystalline waters or lounge in the shallow surf as we curate a personalized day of relaxation and discovery under the sun.