Private Sailing Charters in Greenport & Shelter Island, NY
Sail Selina NY offers private sailing charters aboard Selina II — a 1926 Crosby catboat built in Greenport, NY and sailed by the same family for 100 years. All charters are completely private, limited to six guests, and depart from Greenport Village or Dering Harbor on Shelter Island.
Day Sail — Greenport & Shelter Island
A 2-hour private sail across Peconic Bay and Shelter Island Sound. Departing from Greenport Village or Dering Harbor, you'll move quietly under Selina II's 1,000-square-foot gaff-rigged mainsail — no engine noise, no crowds. Guests are welcome to bring food and drinks aboard.
Duration: 2 hours · Guests: Up to 6 (private, your group only) · Departure: Greenport or Shelter Island · Price: $800 to charter the full boat
Sunset Sail — Peconic Bay
Selina II's most-requested experience. As the sun drops over the North Fork, the 1926 catboat moves silently across Peconic Bay — golden light on the water, no other passengers, no interruptions. An ideal setting for a proposal, anniversary, or simply a remarkable evening.
Duration: 2 hours · Guests: Up to 6 · Departure: Greenport or Shelter Island · Price: $850 to charter the full boat
Private Event Charters — Proposals, Anniversaries & Special Occasions
Book the entire vessel for a proposal, anniversary, birthday, micro wedding, or corporate outing. Captain Luna and her crew handle the experience from start to finish. With a maximum of six guests, there is nothing incidental about any moment on board.
Duration: 2–3 hours · Guests: Up to 6 (full boat, exclusive) · Departure: Greenport or Shelter Island · Price: From $800 for full vessel
Wine Tasting Sails — North Fork Vineyards
Sail Selina NY partners with Peconic Bay Winery and Krissie Vineyards for private wine tasting charters on the water. Taste wines from two of the North Fork's most respected producers while Selina II carries you across the Sound. BYOB-friendly on all charters.
Duration: 2–3 hours · Guests: Up to 6 · Price: From $800 — contact for wine tasting packages
Step Aboard a Piece of Maritime History
Indulge your senses with the scent of freshly varnished mahogany and gleaming brass aboard this elegant 1926 wooden yacht—built right here in Greenport at Sweets Shipyard and still lovingly cared for by the same family after 100 years.
After nearly 100 years of sailing history, this storied vessel has returned home to the East End where her story began. As you glide across the bay, your captain shares stories of Greenport’s shipbuilding heritage, the yacht’s family history, and the North Fork’s rich maritime traditions.
Learn why yachts like SailSelinaNY are varnished—not painted—and enjoy a rare, behind-the-scenes look at the art of operating a classic gaff-rigged sail.
When looking for things to do on the North Fork, plan to set sail from the picturesque shores of Greenport and Shelter Island, aboard our historic wooden yacht, and indulge in a classic day sail across the serene waters of Long Island’s East End. Feel the soft breeze ruffle your hair as you pass charming waterfront villages, with the stunning natural beauty of Long Island’s East End unfolding before you. Book your journey now and create memories on the water that will last a lifetime.
What Guests Say:
"My wife and I sailed aboard Selina II in late September and had a fantastic time. The captain shared so much about the history of the boat and the area..." — Guest review, TripAdvisor
James V., TripAdvisor
"The Captain and her mate were so knowledgeable and engaging. We learned so much about the local waters and the history of this incredible vessel..."
Thomas S., TripAdvisor
“We’ve sailed on the Selina II numerous times, and it never fails to be magical. Beautiful boat, beautiful people, and stunning views.”
Jenny W., TripAdvisor
What to Expect on a Sail Selina NY Charter
Every charter runs the same way: Captain Luna Crowley takes the helm, Selina II's mainsail is raised, and the world goes quiet. Here's what's consistent across every sail:
The boat — Selina II is a 100-year-old Crosby catboat, lovingly preserved. Varnished mahogany, gleaming brass, and a ride that feels nothing like anything else on these waters
The Crew — Captain Luna and her mate bring deep local knowledge of Peconic Bay, Shelter Island Sound, and Greenport's maritime history. Guests who want to learn are welcome at the helm; guests who want to simply sit are equally welcome
The pace — unhurried. Two to three hours of quiet water, open sky, and no agenda
The history — guests consistently say they didn't expect the stories: Operation Sail 1976, the Sweets Shipyard, the Frank Mundus legacy. Captain Luna carries that history naturally
The capacity — six guests, maximum. This isn't a compromise; it's the point
Who This Charter Is For
Couples seeking a romantic, private sailing experience on Long Island — proposals and anniversaries especially welcome
Visitors to Greenport and Shelter Island looking for the most memorable thing to do on the North Fork
Guests staying at The Chequit hotel on Shelter Island — priority booking available for hotel guests in 2026
Families and small groups (up to 6) who want a genuinely intimate experience, not a harbor tour
Wine country visitors exploring the North Fork who want to combine sailing with local vineyard tastings
Day-trippers from the Hamptons, Sag Harbor, or NYC — Greenport is 2 hours from Manhattan, 30 minutes from the Hamptons
Frequently Asked Questions — Sailing Charters in Greenport & Shelter Island
How much does a sailing charter on Selina II cost?
Day sails and sunset sails start at $800 to charter the full boat privately for up to six guests. Private event charters and wine tasting packages are priced separately — contact Captain Luna Crowley at 631-500-0763 or sailselinany@gmail.com for current pricing and availability.
How many people can sail on Selina II?
Can I book a sailing charter for a proposal or anniversary?
All Sail Selina NY charters are limited to six guests maximum. This is by design — Selina II is a 1926 historic catboat, and keeping groups small ensures every guest has a genuinely personal experience. You can book individual tickets or charter the full boat exclusively.
Yes. Private event charters are one of Sail Selina NY's most-requested experiences. Captain Luna and her crew are experienced with proposals, anniversaries, birthdays, and other special occasions. With only six guests aboard, every detail of the experience is personal. Book the full boat exclusively for complete privacy.
Is Selina II good for beginners or people who don't sail?
Where do the sailing charters depart from?
Charters depart from Greenport Village and Dering Harbor on Shelter Island, NY. In the 2026 season, Selina II is also docked at The Chequit hotel on Shelter Island, offering priority booking for hotel guests.
What is the best sailing charter on Long Island's East End?
How long are the sailing charters?
Is it BYOB? Can I bring food and drinks?
Selina II is the only 1926 Crosby catboat available for private charter on Long Island. Unlike typical harbor tour boats or modern charter vessels, Selina II is a living piece of maritime history — built in Greenport, restored multiple times, and sailed continuously by the same family for 100 years. Most guests describe it as unlike anything they've done before.
Standard day sails and sunset sails are 2 hours. Private event charters and wine tasting sails run 2 hours. We also have half day and full day charter availability. Custom durations are available — contact Captain Luna for details.
No sailing experience is required. Guests are welcome to try the helm if they'd like, or simply relax and enjoy the ride. Captain Luna handles everything. The boat moves quietly under sail — there's no engine noise and no rough motion that would concern first-time sailors on calm days.
Yes — Sail Selina NY is BYOB-friendly. Guests are welcome to bring their own food, wine, champagne, or beverages. For wine-focused experiences, Sail Selina NY also offers dedicated wine tasting charters in partnership with Peconic Bay Winery and Krissie Vineyards.