Sailing in Big Pine Key, FL

Private sailing, ocean scenery, and a setting built around your comfort

Charter a private historic schooner sail with drinks and snacks included

Sail the Florida Keys privately aboard a classic sailboat

Settle into a classic schooner for an intimate Key West sunset

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

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

Sail, snorkel, and seek sandbars aboard a private catamaran

Learn sailing fundamentals aboard Hobie Wave catamarans

Sail a 1939 wooden schooner and take a turn at the helm

Private Key West harbor sail with time at the helm

Sail beyond Key West for snorkeling, kayaking, fishing and lunch

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

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

Private catamaran sailing for sunrise or sunset ocean views

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

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

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

Private sailing with an onboard bathroom and kitchen

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

Sail the ocean in privacy with a full bathroom and kitchen onboard

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

Private sailing with a full bathroom and kitchen

Private catamaran sailing with ocean serenity

Sail Key West waters privately with an onboard kitchen and full bathroom