Best results for Sailing in Key West, FL

Adults-only Key West sunset sail with champagne and gourmet cheese

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

Private Key West sunset sail with your music and a flexible start time

Sail Key West waters on a private 4-hour charter for up to six guests

Spend a full day sailing from Key West with up to 6 guests

Charter the 54-foot Schooner Valora for a private sail in Key West

Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

Private sail to a shallow-water anchorage with time to lounge on a Lilypad float

Private 2-hour Key West sunset sail with captain and mate

Private Key West harbor sail with time at the helm

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

Sail Key West at sunset with complimentary champagne and drinks

Choose your boat and learn to sail with a private instructor in Key West

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

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

Sail, swim, and brunch with bottomless mimosas on SV Argo Navis

Private 3-hour Key West sunset sail with time to snorkel

Sail into the Key West sunset on a private 3-hour catamaran charter

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

Private 2-hour sail on a 1939 wooden schooner in Key West