Sailing in Big Pine Key, FL

Private catamaran sailing with a full bathroom and kitchen

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

Sail Key West waters on a private catamaran timed for sunrise or sunset

Spend a private day on a clothing-optional sailing catamaran

Sail the ocean on a private catamaran with a full bathroom and kitchen

Spend the day sailing Key West waters aboard a private catamaran

Sunday sailing with brunch bites and bottomless mimosas

Sail Key West’s historic waterfront aboard a hand-built 86-foot schooner

Private catamaran celebration with bubbly, wines, and party platters

Sail Key West on Schooner America 2.0 with complimentary soft drinks

Sail a 1930 schooner into the Key West sunset

Sail into Christmas morning with brunch, mimosas, and Key West views

Hoist sails and take the wheel aboard a 2-masted schooner

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

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

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Sail Key West's night waters beneath the full moon aboard a 105-foot schooner

Sail Key West aboard a 1939 wooden schooner built for General George S. Patton

Charter a sailboat in Key West for up to 42 guests

Sail Key West’s waters aboard a 105-foot schooner with Christmas brunch and drinks

Sail Key West’s Atlantic coast at sunset aboard a historic schooner

Join Key West schooners in a monthly race to Sand Key Lighthouse

Take the helm or relax beneath the sails on a private classic schooner

Sail into Key West sunset views with holiday treats aboard a 105-foot schooner