Full-Day Private Sailing Charter | Long Island Getaway from Greenport & Shelter Island
Quick Details
Greenport Village or Shelter Island’s Dering Harbor
📍 Departures
8 hours (customizable full-day itinerary)
🕗 Duration
Up to 6 guests – private charter only
🍒 Picnic Lunch
Leave it to us or bring your own
👥 Capacity
🍷 BYOB
Bring your favorite North Fork vineyard wine and picnic lunch (glassware, water & ice provided)
Tour Dering Harbor, Greenport waterfront, Shelter Island coves, and Peconic Bay
🔥 Highlights
Luxury sailing, sightseeing, relaxation, and hands-on sailing (optional)
🌿 Experience
Ideal for anniversaries, birthdays, or group getaways – professional photo add-on available
🏆 Bonus
A Full-Day Private Sail on Peconic Bay
Escape to the sparkling waters of the North Fork aboard SailSelinaNY, a beautifully restored 1926 historic wooden yacht, for an unforgettable 8-hour private charter. Departing from Greenport Village or Shelter Island’s Dering Harbor, begin your adventure with a scenic cruise past working marinas, historic shipyards, and classic waterfront architecture.
This full-day Long Island private yacht charter lets you set the pace—sail, anchor, explore, celebrate, or simply relax as we follow the wind across the shores of the North Fork of Long Island’s East End.
This is the ultimate private sailing tour Long Island visitors dream of — exclusive, customizable, and designed just for your group.. SailSelinaNY is one of the most exclusive boat tours on Long Island, offering private access to the best coastal scenery around Shelter Island and Greenport.
A classic yacht cruise is one of the most memorable parts of a Long Island weekend getaway, especially when you set sail aboard a historic 1926 wooden yacht.
Whether you’re planning a Shelter Island family boat tour, a North Fork family vacation, a romantic anniversary sail, a birthday celebration on the water, or a fun girls’ day out, this private charter lets you relax, explore, and create unforgettable memories on your own terms.
This Greenport yacht charter includes an 8-hour private getaway exploring Greenport’s harbors, Shelter Island’s shoreline, and the North Fork coastline — your chance to experience the water, history, and luxury all in one day.
✨ Reserve your private full-day sail now — spaces are limited each season!
Set Sail Into Adventure
From the moment the sails lift, you’ll feel the crisp salt-kissed breeze, hear the gentle creak of polished timbers, and watch sailboats glide across the sparkling bay. Families love raising the sails, steering the yacht, and becoming part of the sailing experience. Kids learn how sailboats work — while adults can simply kick back, soak in the sun, and enjoy the ever-changing scenery.
Discover secret coves, hidden beaches, and quiet waters where ospreys soar overhead and the charm of the North Fork comes alive. Bring a picnic, your favorite North Fork Vineyard wine, or your go-to snacks — our crew handles the rest. We are here to make your private yacht charter turnkey so you can simply enjoy the serenity as we drift past historic landmarks and beautiful coastlines.
Experience the Day
Morning Sail
Start your adventure exploring the harbors of Greenport and Shelter Island. Feel the morning breeze, breathe in the fresh salt air, and watch the sunlight dance on the water — a truly magical way to begin your full-day family sailing adventure. Enjoy panoramic views across Peconic Bay and Shelter Island Sound — the heart of Long Island’s East End sailing.
Midday Stop
Anchor in a secluded cove for a leisurely break. Swim in calm, clear waters, enjoy a picnic lunch, or sip local Long Island wine while surrounded by the peaceful beauty of Peconic Bay. Kids will love spotting wildlife, learning the ropes, and discovering why this area is one of the top things to do with kids on Long Island.
Afternoon Return
As the sun softens, hoist the sails once more and glide past Shelter Island’s shoreline. The golden light reflecting on the water, the gentle rocking of the yacht, and the laughter of your family make for a perfect close to a day full of memories.