Best results for Sailing in Key West FL

Sail to a Key West sandbar with snorkeling, snacks, and sunset views

Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

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.

Sip fine wines on a relaxed schooner sail at sunset with craft beers and gourmet bites

Charter a private historic schooner sail with drinks and snacks included

Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

Private 2-hour sunset sail for up to 30, with wine, beer, and hors d'oeuvres included

Charter a sailboat in Key West for up to 42 guests

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Enjoy a Key West sunset with live music, appetizers, and complimentary beer, wine, champagne, and margaritas

Relax on a 2-hour noon catamaran cruise on West Grand Traverse Bay

Sail the Nauti-Cat on a 1.5-hour kids cruise in Traverse City

Sail a luxury catamaran along Palm Beach and savor a scenic two-hour sunset cruise.

See wild dolphins, snorkel with turtles, and enjoy lunch on a 3-hour West Oahu sail

Unwind on a West O‘ahu sunset cruise with panoramic views, drinks, and light bites included

Sail Kaanapali and snorkel top West Maui reefs with breakfast, lunch, and open bar

Sail West Grand Traverse Bay on a 2-hour happy hour cruise

Sail West Grand Traverse Bay at sunset with a champagne toast

Sip cocktails as the sun sets on a 2-hour West Maui sail with open bar and appetizers

Enjoy a 2-hour sunset sail with catered dinner and a complimentary premium bar

Sail Provincetown Harbor and Cape Cod Bay on a private 6-hour charter

Savor a buffet dinner and open bar aboard a luxury catamaran at sunset

Glide across West Bay at sunset as you savor local food and drinks

Sail from West Bay Beach for lively afternoon winds and scenic peninsula views

Experience a relaxing afternoon sail with regional food and open bar