2-Hour Long Island Sailing Tour | Greenport & Shelter Island Yacht Experience
East End of Long Island’s North Fork Sailing Tours from Greenport & Shelter Island
Historic 1926 wooden yacht
Built in Greenport, sailed beautifully by the same family for 100 years.
Depart from both harbors
Greenport Village or Shelter Island.
Perfect for Getaways
Hamptons, Sag Harbor, and NYC day trips.
2-hour sail in Greenport & Shelter Island
Choose individual tickets or book the whole yacht
Luxury small-group experience
Max 6 guests per sail
Hands-on or hands-off
Try the helm or relax in the captain's chair
Sail The East End & Dering Harbor
Calm waters, stunning shoreline views.
A must-do experience on Shelter Island + the North Fork
Ready to embark on an unforgettable adventure? Step aboard and become a valued member of our crew on this two-hour classic sailing tour, where you can opt to help raise the sails and experience the thrill of traditional yacht sailing firsthand.
Or, if you prefer to just relax and take in the views, settle into your traditional captain’s chair, breathe in the salt air, and lose yourself in the natural beauty of Greenport’s waterfront, Dering Harbor’s endless boat collection on Shelter Island, and the open waters of the idyllic Peconic Bay.
Our Shelter Island boat tours are one of the most popular Sailing Tours Long Island offers, combining historic charm with hands-on sailing, perfect for couples, families, and small groups.
Unique, upscale, and intimate, SailSelinaNY limits her passengers to just six guests, creating an exclusive and relaxed atmosphere where every sail feels like a private adventure. Book your North Fork sailing charter today!
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.
Your North Fork Sailing Experience
Departing from either Greenport Village docks or Shelter Island’s Dering Harbor, your personalized tour showcases the North Fork’s charming waterfronts, cedar-shingled homes, and scenic harbors.
We’ll pass the Shelter Island Ferry, spot ospreys nesting along the channel, then head into Peconic Bay to raise sail and follow the wind wherever it takes us. Whether you’d like to participate as crew or simply sit back, relax, and soak in the sea air, we’re here to make your SailSelinaNY sailing experience truly unforgettable.
Among Long Island sailing tours, SailSelinaNY stands out for its intimate group size, historic yacht, and personalized storytelling about Greenport and Shelter Island. Looking for a North Fork coastal adventure? Discover an East End sailing experience unlike anything else. Limited to 6 guests per sail — book early to secure your spot!
The Top-Rated Sailing Experience on Long Island’s East End
My wife and I sailed aboard the Selina II in late September and had a fantastic time. The captain shared wonderful stories about the boat’s history, and the crew made us feel at home. We caught a beautiful sunset—just magical.”
James V., TripAdvisor
The Captain and her mate were so knowledgeable and engaging. We learned so much about the local waters and enjoyed a relaxing afternoon on the bay. Highly recommend!
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 - Relaxation, Romance & VIP Service on the Water
-
Our lovingly preserved 1926 catboat offers a luxurious, comfortable sail. Guests consistently praise her pristine condition and classic beauty.
-
Our welcoming crew enhances every trip with local knowledge, sailing expertise, and personal hospitality.
-
What began as a passion project has evolved into something more. We’re proud of where we’ve been and even more excited for what’s ahead. What sets us apart isn’t just our process—it’s the intention behind it. We take time to understand, explore, and create with purpose at every turn.
-
Hear fascinating tales of Greenport’s shipyards, Shelter Island’s history, and the North Fork’s deep sailing legacy.
-
Sailing with us helps preserve a living maritime treasure—a one-of-a-kind link to Long Island’s yachting past.
Guests often tell us this feels like one of the best boat tours on Long Island, thanks to the small-group setting, historic yacht, and personalized storytelling on every sail. As one of the top Greenport yacht charters, SailSelinaNY offers a unique experience aboard a fully restored 1926 wooden yacht – perfect for families, couples, or friends looking for a classic sailing adventure.
Who This Exclusive Cruise is For
Couples looking for a romantic getaway
Families wanting a peaceful sail
Small groups of friends looking to reconnect
Babymoons -peaceful, gentle, and perfect for those unforgettable pre-baby memories
Mini Moons, for a quick East End getaway after your special day
Weekend coastal retreats near the Hamptons, NYC, and the North Fork
The perfect setting for anniversaries, birthdays, engagements, girls’ getaways, and even babymoons—quiet sails, calm waters, and a peaceful atmosphere for celebrating life’s biggest moments.
Whether you’re planning a Long Island weekend getaway or a day trip to the North Fork, a sail aboard SailSelinaNY is the perfect way to experience the East End from the water. Our 2-hour classic sail is the perfect Hamptons day trip add-on, giving you a chance to leave the crowds behind.
Looking for something else? Try our evening Sunset Sails and Moonlight Sails or Private Charters
Amenities Designed for East End Leisure & Luxury
Weather
Safety first—sails may be canceled for bad weather at no charge. We sail in light mist but not in heavy rain.
Beverages
Sodas available for sale, bottled water complimentary. 🍷 BYOB no cork fee, super nice, so bring a cooler if you like!
Swag
Visit our SailSelinaNY Ship’s Store for embroidered hats, polos, hoodies, wine glasses and can koozies—available online or onboard.
Seating
Cushioned settees and vintage captain’s chairs ensure comfort and visibility. Guests may also sit forward on the cabin top if sure-footed.
Attire
Wear comfortable, soft-soled shoes; bring a camera and light jacket in spring or fall.
Safety
All modern safety gear onboard, tastefully concealed to preserve her vintage charm.
Max 6 Guests
Children of all ages welcome! Coast Guard–approved life jackets available for all sizes.
Cancellations
Private charters up to 72 hours. Individual bookings refundable up to 24 hours prior.
Restroom
Clean marine head onboard; shoreside restrooms also available before departure.
Accessibility
Crew assists guests as needed. Two easy steps into the cockpit; boarding generally level with the dock.
Parking
Convenient parking at Mitchell Park Marina in Greenport or near Shelter Island docks.
Location
Greenport & Shelter Island are just a short ferry ride from Sag Harbor, a perfect day trip from the Hamptons, an easy day trip from NYC and super accessible for Long Island couples. Taking a 2 hour sail with SailSelinaNY is one of the many things to do during your Shelter Island vacation.
Experience one of the best boat tours on Long Island by choosing the most intimate Sailing Tours Long Island offers aboard a 1926 historic wooden sailing yacht, and pick the best with our top-rated Shelter Island boat tours for sailors of all ages.
Ready to experience Long Island’s most exclusive sailing adventure? Choose a shared or private two-hour cruise aboard SailSelinaNY, our family boat built in Greenport and still sailing strong 100 years later.
Please note: If you are not booking a private charter, this sail requires two or more people. Amusement tax and crew gratuity added on.