Up to 6 Guests • All Ages • 2 Hours
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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Light activity; no special fitness required—accessible to most people who can climb a short ladder and stand on deck.
Wildlife
History
Shelter Island and nearby Greenport have deep maritime roots; Greenport’s waterfront and Mitchell Park reflect a long history of shipbuilding and fishing on the North Fork.
Conservation
Peconic Bay supports eelgrass and scallop habitats—avoid anchoring on eelgrass beds and carry out all trash; small-group sailing helps minimize disturbance.
Sail Selina NY
Up to 6 Guests • All Ages • 2 Hours
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.
Historic Yacht
Selina II
Classic wooden vessel
Location
Shelter Island Heights
Launching point for all trips
Private & Public
Charters & Sails
Small-group experiences
Trips Offered
10 Experiences
From lessons to weddings
Book a 2-hour classic sail, private lesson, or full-day charter departing from Shelter Island Heights — limited daily departures.
Arrive to the correct marina
Confirm your departure point—Shelter Island – Dering Harbor or Greenport Village – Mitchell Park Marina—and arrive 15 minutes early to board.
Dress in layers
Wind and spray can make temperatures feel cooler on open water; bring a windproof layer and a light hat.
Plan for motion sensitivity
If you’re prone to seasickness, take a preventative medication before boarding and sit mid-boat where motion is least noticeable.
Book the limited seats early
With a six-guest maximum, weekend slots fill quickly—reserve in advance, especially for sunset sails or celebrations.
Non-marking deck shoes
Protects the wooden decks and gives grip when moving about the boat.
Windproof jacket
Blocks breeze and light spray during cooler mornings and evenings.
spring
Sunscreen & sunglasses
Essential for sun exposure on open water, especially during midday sails.
summer
Motion-sickness medication
Useful for guests prone to seasickness—take before boarding for best effect.