Best results for Sailing in Key West, FL

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

Learn at your own pace with private instruction on the water

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

Sip bubbly and sail into the Key West sunset aboard a spacious catamaran

Private catamaran sailing with champagne, wines and a gourmet cheese buffet

Sail, snorkel, and seek sandbars aboard a private catamaran

Private Key West sailing with snorkeling, sandbars, and dolphin searches

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

Customize a private day on the water with snorkeling and onboard lunch

Sail Key West waters with drinks, onboard gear, and a freshwater rinse

Toast the sunset with champagne aboard a private 47-foot sloop

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

Sail, snorkel, and explore Key West waters on your private catamaran

Sail, kayak, and snorkel Key West's shallow waters on a private cruise

Sail Key West’s reefs, barrier islands, and mangroves

A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

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

Settle into a classic schooner for an intimate Key West sunset

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