Help raise sails aboard the classic wooden yacht Selina II or relax as the moon lifts over Shelter Island and the North Fork. Two-hour evening sails with optional charcuterie, bubbly, and photographers make this a perfect small-group celebration.
Help raise sails aboard the classic wooden yacht Selina II or relax as the moon lifts over Shelter Island and the North Fork. Two-hour evening sails with optional charcuterie, bubbly, and photographers make this a perfect small-group celebration.
Book with Sail Selina NY
Verified experiences and guided adventures in the surrounding area.
Operated by Sail Selina NY · Shelter Island Heights, New York
easy.
2 hours.
Minimal fitness required—able to step onto a small yacht and stand for short periods; mobility considerations apply for boarding.
The Moonrise Cruise is two hours long, designed to position the vessel for moonrise over open water.
Yes—guests are welcome to assist with raising sails and basic line work under crew supervision.
No specific age provided; families often sail but infants and very young children should be supervised and wear life jackets if required.
Bring medication or acupressure bands; sit mid-ship and stare at the horizon for best results, and inform crew if you feel unwell.
Food and premium beverages are optional add-ons—charcuterie boards and chilled bubbly are available for purchase and should be booked early.
Use the operator referral link to check availability and make reservations; weekend summer sails often sell out, so book ahead.
Shelter Island has long been a working maritime place; classic yachts and ferry routes have shaped local life for centuries, and Selina II continues that wooden-boat tradition.
The operator encourages no-trace practices—avoid disturbing haul-out sites, pack out trash, and minimize single-use plastics on board.
Sail Selina NY operates from Shelter Island Heights, New York, offering passenger sailing experiences aboard Selina II, a restored historic wooden yacht. The business offers scheduled public sails and private charters that include the 2-Hour Classic Sail, Family Sailing Charter, Moonrise Cruise, Romantic Champagne Sunset Sail, Half-Day and Full-Day Private Charters, Private Sailing Lessons, Nautical Wedding Package, private engagement and proposal sails, and bachelorette party experiences. Trips navigate the calm waters of Shelter Island, Peconic Bay, and the North Fork, with routes tailored to weather, tides, and guest preference. Guests may participate in raising sails and steering or choose to relax with Bluetooth music and scenic views. Private Sailing Lessons focus on helm control, sail trim, basic navigation, and safety procedures, suitable for beginners and intermediate sailors. Half-day and full-day charters allow anchoring in quiet coves for swimming, sunbathing, and picnics. The Nautical Wedding Package and private proposal sails are staged aboard Selina II for intimate waterfront ceremonies and announcements. Moonrise and Sunset cruises highlight shelter island and North Fork vistas during golden hours. Operations center in Shelter Island Heights, emphasizing small-group, personalized experiences aboard a classic wooden yacht that preserves maritime character. All offerings are delivered subject to seasonal scheduling and local regulations; trips may be adjusted for weather and sea conditions to ensure guest safety. Selina II’s vintage lines and wooden construction contribute to a classic sailing atmosphere, while Shelter Island’s sheltered bays provide calm conditions ideal for family outings, lessons, and special events throughout the sailing season.
Book with Sail Selina NY