Sailing in Stock Island, FL

Sunset catamaran sail with live music, appetizers, and included drinks

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

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

Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

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 a 1930 schooner into the Key West sunset

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

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

Private catamaran celebration with bubbly, wines, and party platters

Sail a restored 1925 schooner at sunset with drinks and charcuterie

Charter a sailboat in Key West for up to 42 guests

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

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

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

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

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

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

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

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

Sunday sailing with brunch bites and bottomless mimosas