Half-Day Private Sailing Charter
Long Island Yacht Cruise from Greenport & Shelter Island
Quick Details
Greenport Village or Shelter Island’s Dering Harbor
📍 Departures
4 hours (customizable half-day itinerary)
🕗 Duration
Up to 6 guests – private charter only
🍒 Picnic Lunch
Leave it to us or bring your own
👥 Capacity
Bring your favorite North Fork vineyard wine and picnic lunch (glassware, water & ice provided)
🍷 BYOB
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
Capture stunning family or couple photos aboard this historic 1926 yacht
💡 Great Idea
A Half-Day Private Sail on Long Island’s North Fork
Step aboard our classic 1926 wooden sailing yacht, lovingly built at Sweets Shipyard in Greenport and cared for by the same family for nearly a century. Your half-day private sail offers four hours of relaxation, exploration, and adventure on the sparkling waters of the East End of Long Island NY.
SailSelinaNY is one of the most exclusive boat tours on Long Island, offering a private yacht experience that blends luxury sailing, hidden coves, and unforgettable coastal scenery.
Cruise past Greenport’s working waterfront, explore the hidden coves and picturesque beaches of Shelter Island, and soak in the rugged, natural beauty of the North Fork coastline. Whether you’re seeking a romantic anniversary sail, a girls’ day out, a family adventure, or simply a unique North Fork experience, this private charter lets you set your own pace and create lasting memories.
Set Sail Into Adventure
Relax on deck with the warm sun on your face and the fresh salt breeze in your hair, or join the crew to raise the sails, steer the yacht, and learn hands-on sailing techniques. This is a true luxury yacht charter experience designed for guests who want privacy, space, and a personal connection to the water. Your captain will share stories of Greenport’s shipbuilding heritage, the yacht’s storied history, and the maritime culture that has shaped Long Island’s East End.
After 25 years sailing the Chesapeake Bay, the historic SailSelinaNY has returned home to Long Island’s East End, continuing a legacy of craftsmanship, adventure, and family tradition that spans four generations. Now, she welcomes guests aboard to experience the timeless joy of classic sailing NoFo (on the North Fork) in Greenport, Shelter Island, and beyond.
Midday Picnic & Relaxation
Pack a light picnic or bring along a bottle of your favorite North Fork wine or local craft beer—your crew takes care of the rest. Stretch out on deck, savor local flavors, and watch the water shimmer around you. This four-hour cruise strikes the perfect balance of adventure and relaxation—ideal for anniversaries, birthdays, family getaways, or a memorable girls’ day out. Take a deep breath, slow down, and simply enjoy the moment.
Guest Experience
🌊 Sensory-Rich Sailing
Hear the gentle creak of polished timbers, feel the wind in your hair, and breathe in the salt air as you glide across Peconic Bay.
🍇 Local Flavors
Pair your picnic with Long Island wines from nearby North Fork vineyards.
👩 Expert Captain
Learn about sailing and maritime history while enjoying a fully personalized experience.
Among private boat tours on Long Island, SailSelinaNY stands apart for its historic yacht, small-group exclusivity, and personalized captain-led experience.