Best results for Sailing

Private sailing with dolphin sightings on Saint Helena Sound

Set your own pace with offshore sailing and swim stops

Customize your private sail with ocean cruising or time in the water

Set your own course, with an option to anchor and swim

Private sunset sailing with room below deck for passing weather

Refine your sailing technique and build confidence on the water

Private bachelor sail with drinks, snacks, and daytime or sunset departures

Build your sailing skills with instructor-guided time on Oyster Bay Harbor

Step aboard CHRISTEEN to see harbor sights and learn its story

Build practical sailing skills with hands-on Flying Scot instruction

Sail the Middle River and Chesapeake aboard a private luxury catamaran

Sail privately with your group aboard S/V Endless Summer

Private catamaran sail with an island or swim stop

Celebrate, sail, and spot coastal wildlife on a private outing

Private catamaran sailing with space to swim, paddle, and unwind

Sail Tampa Bay at golden hour aboard a 40-foot luxury catamaran

Private, wind-driven sailing aboard a 48-foot Jeanneau yacht

Private sailing with spacious lounges, swim access, and Sarasota Bay views

Sail Tampa Bay aboard a private 48-foot Jeanneau yacht

Sail into golden hour with four spacious places to gather aboard

Sail, swim, and enjoy massage time on a private ocean spa escape

Private catamaran views of Waikiki’s Friday fireworks

Private Friday-night sail with sunset, city lights, and Waikiki fireworks views

Build windsurfing skills with a lesson designed for young sailors