Historic wooden yacht charters, lessons, and sunset cruises on calm Peconic Bay waters.
Choose from classic 2-hour sails, family charters, moonrise and sunset cruises, private lessons, and bespoke event packages.
boat-charters · Shelter Island Heights
Board Selina II for a relaxed, two-hour sail around Shelter Island and Peconic Bay. Small-group, hands-on sailing on a historic wooden yacht with optional charcuterie, bubbly, and photography add-ons.
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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Classic wooden vessel
Launching point for all trips
Small-group experiences
From lessons to weddings
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sail Selina NY listing.
Sail Selina NY offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Book a 2-hour classic sail, private lesson, or full-day charter departing from Shelter Island Heights — limited daily departures.
boat-charters · Shelter Island Heights
Board Selina II for a two-hour, family-friendly sail on Shelter Island and Peconic Bay. Small groups, optional hands-on sailing, and curated add-ons make this historic wooden-yacht cruise perfect for celebrations or a relaxed afternoon on the water.
boat-charters · Shelter Island Heights
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.
boat-charters · Shelter Island Heights
Master sail trim, helm control, and basic navigation in a private two-hour lesson on Peconic Bay. Learn hands-on aboard a historic wooden yacht out of Shelter Island Heights with instruction tailored to beginners and intermediates.
boat-charters · Shelter Island Heights
Toast the sunset aboard Selina II: a two-hour private wooden-yacht sail across Shelter Island’s calm Peconic Bay, ideal for proposals, anniversaries, or an intimate evening with bubbly and golden-hour light.
boat-charters · Shelter Island Heights
Step aboard Selina II for a private four-hour sailing escape through Shelter Island coves and the North Fork. Swim, sunbathe, learn to trim sails, or simply savor a curated picnic as the captain sets the pace.
boat-charters · Shelter Island Heights
Spend a private day aboard Selina II, a classic wooden yacht cruising Shelter Island and Peconic Bay. Swim, learn to sail, enjoy a curated picnic, and explore quiet anchorages with a maximum of six guests.
boat-charters · Shelter Island Heights
A private two-hour sail from Shelter Island Heights designed for proposals and intimate celebrations—customizable add-ons like flowers, charcuterie, and a photographer make this a turn-key, private experience on Gardiners Bay. Book sunset slots early for the best light.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.