Best results for Sailing in Key West FL

Sip and sail into the Key West sunset with live music and an open well bar

Sail Key West on Schooner America 2.0 with complimentary soft drinks

Sail into the Key West sunset with drinks and hors d'oeuvres included

Sail a luxury catamaran at sunset with tapas, drinks, and dolphin watching

Sail Key West at sunset with complimentary champagne and drinks

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

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

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