Best results for Sailing in Key West, FL

Sail privately in a clothing-optional setting shaped around your comfort

Spend a private day on a clothing-optional sailing catamaran

Sail the Florida Keys privately aboard a classic sailboat

Learn sailing fundamentals aboard Hobie Wave catamarans

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 1939 wooden schooner and take a turn at the helm

Sail a 1930 schooner into the Key West sunset

Sail Key West aboard a 1939 wooden schooner with captain and crew

Brunch, drinks, and a swim stop aboard a Key West sail

Sunday sailing with brunch bites and bottomless mimosas