Discover amazing Key West activities and premium in-home experiences.
Key West is a coastal destination in Central Florida, where you'll find sun-soaked beach days, fun for families. Whether you're seeking relaxation, exploration, or local flavor, this vibrant spot has something for everyone.
Enjoy a private six-hour cruise with captain, mate, fuel, and gear provided
Customize your private 4-hour cruise for up to 6 guests with crew, fuel, and gear included
Enjoy cold A/C, a smooth ride, and comfortable deep-sea fishing for all levels
Fish the reefs for snapper and grouper with bait, tackle, license, and a helpful crew included
Enjoy a four-hour private cruise to mangrove sandbars with snorkeling, paddle boards, and a catered Cuban lunch.
Discover mangrove islands and pristine sandbars on a comfortable 25-ft Sea Ray with captain and fuel included
Enjoy a customizable cruise through Florida Keys sandbars with snorkel gear and coolers included.
Spot playful dolphins and snorkel vibrant reefs on a small-group Key West cruise
Savor fresh sushi and drinks as you glide past Key West landmarks at sunset
Taste Key West favorites and trace Hemingway’s footsteps on a guided 2-hour stroll
Follow Buffett's story through Old Key West with local guides, pie, and drinks
Explore Hemingway's Key West haunts while savoring local food, cigars, and rum on a four-hour guided walk
Circle Key West on new jet skis with 5–6 scenic stops and lively guide insights.
Soar up to 300 feet above Key West on a 10–12 minute parasail flight guided by a USCG-certified crew
Snorkel Key West’s vibrant reef aboard a fast catamaran with breakfast and post-trip drinks.
Captain a two-person boat to secluded sandbars and mangrove islands.
Swim at a secluded sandbar and watch playful wild dolphins up close, with lunch and unlimited beer and wine included.
Paddle mangrove tunnels then relax on a secluded sandbar with lunch and unlimited drinks
Enjoy unlimited drinks, appetizers, and live music aboard a catamaran while you watch the famous Key West sunset.
Snorkel two vibrant reefs, then unwind with unlimited drinks aboard a sunset catamaran
Spend a full day on the water with 11 activities, lunch, drinks, and a parasail flight
Enjoy 8–15 minutes of parasailing with smooth boat takeoff and panoramic Key West views.
Paddle mangrove tunnels, then unwind at a secluded sandbar with lunch and unlimited drinks
Sail past Key West landmarks on a 105-ft schooner while enjoying complimentary soft drinks and expert crew narration.
Sip complimentary champagne as you watch a legendary Key West sunset aboard the elegant Schooner America 2.0.
Snorkel two reef sites, then enjoy an all-you-can-eat Low Country seafood boil with premium open bar
Cruise to an iconic sandbar aboard a spacious tiki boat for 3.5 hours
See coral reef life through glass viewing windows from an air-conditioned catamaran
Experience parasailing, jet skis, banana boat, and an ocean waterpark in one action-packed outing
Ride a guided 28-mile loop past Mallory Square and the Southernmost Point
Explore Key West on a guided 28-mile jet ski tour with experienced guides
Snorkel North America’s only living coral reef with gear, instruction, and included drinks
Enjoy a Key West sunset with live music, appetizers, and complimentary beer, wine, champagne, and margaritas
Watch wild dolphins and snorkel the backcountry with gear, guidance, and complimentary beverages on a fast catamaran
Snorkel two reef sites on a fast catamaran with gear and drinks included
Snorkel North America’s only living coral reef with gear, instruction, and drinks included
Snorkel North America’s only living coral reef, then enjoy a sunset sail with reggae and complimentary drinks
Soar above Key West for gentle takeoffs, expert crew, and panoramic views
Fish calm flats and backcountry for tarpon, permit, and bonefish with a licensed captain
Reef fishing aboard a spacious vessel with AC galley and restrooms, ideal for families, friends, or corporate groups
Key West is the southernmost point in the continental U.S., where turquoise waters, pastel architecture, and a quirky, laid-back vibe create one of Florida’s most iconic destinations. It’s a place where history, art, and ocean adventure blend seamlessly into every block and every sunset.
Start your day with Cuban coffee and a bike ride past colorful conch houses and banyan trees. Tour Hemingway’s house, snorkel at Fort Zachary Taylor, or set out on a boat for a day of reef diving. As the sun sets, Mallory Square comes alive with street performers and live music, followed by fresh seafood, craft cocktails, and dancing under the stars.
Greetwell guests in Key West can enjoy private sunset sails, in-home chef experiences featuring island flavors, or wellness services like massage and guided mindfulness walks along the beach. Whether you’re here for the parties or the peace, Key West lets you do island life your way.