How many guests can the charter accommodate?

The Full-Day Private Charter is limited to up to 6 guests for a private-feeling sail.

Can I participate in sailing the boat?

Yes — guests are welcome to help raise sails, trim sheets, and learn seamanship under crew guidance.

A curated picnic is available as an add-on; otherwise guests may bring their own provisions and snacks.

What should I do about seasickness?

Bring any personal medications or ginger remedies; the crew can steer for calmer water if needed, but preparation is best.

Where does the charter depart from?

The listing notes Shelter Island Heights as the location; final meeting details are provided at booking or by the operator.

Can you be dropped off at a local restaurant?

Yes — with prior coordination the crew can arrange a drop-off at select local restaurants on Shelter Island.

Sail the Selina II: Private Full-Day Yacht Charter Around Shelter Island & Peconic Bay

On the water off Shelter Island, New York, a day aboard the Selina II delivers classic sailing, quiet anchorages, and panoramic views of Peconic Bay. This full-day private charter leaves from Shelter Island Heights and traces the shallow, glassy waters between the North and South Forks—Greenport, sandbars, marsh channels, and the occasional lobster skiff slide past the rail. The Selina II is a traditional wooden sailing yacht limited to six guests, which keeps the deck uncrowded and the experience intimate: you can learn to raise the sails, stand at the helm, or stretch out with a curated picnic and a book.

Peconic Bay is an estuary system of tidal flats, eelgrass beds, and salt marshes that shape the region’s light and wildlife. Key features on a typical day include the calm coves of Shelter Island, the working waterfront of Greenport, and long stretches of open bay that invite anchoring and swimming. Geology here is glacially scoured coastal plain—shallow shoals and sandy flats—so captains pick their channels carefully; that local seamanship is part of the attraction. On the Selina II you’ll notice teak and varnish, brass fittings, and the tactile rhythm of lines and winches that recall a pre-motor era of New England sailing.

Why book this charter? The small group size, classic craft, and optional hands-on instruction set it apart from larger tour boats. Operators curate optional add-ons—charcuterie boards, bubbly, photographers, even a custom sail message—so the trip can shift from an educational sail to a celebration. The crew’s familiarity with Shelter Island’s anchorages and restaurant drop-offs turns logistics into a relaxed kind of luxury: you spend your day on the water, not worrying about parking or ferry schedules.

Practical notes: the outing runs about eight hours, so expect half a day punctuated by swims and shore stops. The bay’s wildlife includes ospreys and grey seals, and photographers will find low, reflective light midmorning and late afternoon. Families, small groups, and couples appreciate the private-feel and the option to participate in sail-handling. Whether you’re learning points of sail for the first time or want an elegant day afloat, the Selina II offers a hands-on way to experience Shelter Island and the broader Peconic Bay with intimacy and style.

Expect a relaxed, crew-led rhythm: coffee and morning light as sails go up, a midday anchor for swimming and lunch, and a cruise home with late-afternoon breezes. The charter limit of six keeps conversations intimate and service attentive; music via Bluetooth lets you play your playlist against varnished wood. Bring refillable water, reef-safe sunscreen, a light jacket for on-deck wind, and willingness to learn — stepping in to trim a sail gives the kind of perspective only time afloat can deliver.

About Sail Selina NY

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.