Family Sailing Charter | Long Island from Greenport & Shelter Island, NY
Quick Details
📍 Location
Departs from Greenport Village or Shelter Island’s Dering Harbor
Approximately 2 hours (longer sails available upon request)
⏱ Duration
Up to 6 guests — perfect for families or multigenerational groups
👨👩👧 Capacity
All ages welcome — infant, youth, and adult life jackets provided
🎂 Ages
No sailing experience required (participation optional)
⛵ Experience Level
Bring your favorite North Fork wine or snacks; glassware and water provided
🍷 BYOB
Connect your family playlist via Bluetooth
🎶 Music
Keep an eye out for ospreys, fish, and dolphin in season
🐐 Wildlife
Bring your camera — this vintage yacht makes the perfect family photo backdrop! Serious Christmas Card possibilities
❓ Tip
For families our private boat tours on the North Fork provide the perfect blend of relaxation, sightseeing, and hands-on sailing aboard a historic family yacht.
💡Option
A Family Adventure on the Water
Looking for unforgettable family sailing in Greenport or thoughtful North Fork family vacation ideas? Step aboard SailSelinaNY — a historic wooden yacht lovingly restored from 1926 — and treat your loved ones to an experience they’ll talk about for years.
For families seeking a Long Island private charter experience, SailSelinaNY offers a safe, comfortable, and completely customizable way to explore the bay together.
If you’ve been searching for meaningful family activities on Long Island, this private sailing charter offers something far more special than a typical day at the beach or a crowded attraction.
Departing from either Greenport Village or Shelter Island’s Dering Harbor, this private family charter offers a two-hour journey across the shimmering waters of Peconic Bay, perfect for families seeking something meaningful, engaging, and truly local. SailSelinaNY has been in the same family for 100 years!
This is one of the most memorable Shelter Island boat tours for kids and parents alike.Create memories that will last a lifetime aboard a classic 1926 yacht.
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 waterswhere ospreys soar overhead and the charm of theNorth Forkcomes 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.
Where Family Time Meets the Magic of the Bay
From the moment you step aboard, the warm scent of varnished wood, the creak of handcrafted timbers, and the gentle lift of the sails transport you to another era. Kids love helping raise the sails, spotting osprey nests, and learning how wind meets water — making this one of the most engaging Greenport kid’s activities on the North Fork.
Whether you’re:
introducing little ones to sailing lessons for kids,
planning a relaxed Shelter Island family boat tour,
searching for truly unique things to do with kids on Long Island, or
simply wanting to reconnect to loved ones as you glide across the bay……SailSelinaNY offers a peaceful, screen-free adventure that brings families closer together.
Parents love this option as one of the most memorable Sailing Tours Long Island families can experience together.
Curious Crew?
Visit the birthplace of Peter Pan in America and hear how Shelter Island inspired the real-life Neverland—complete with pirates, fairies, and flying imagination.
Step into the world of the Grand Sachem of Long Island, the legendary leader of the Native American peoples who protected these waters centuries ago.
Search for pirate treasure! Shelter Island is one of the rumored hiding spots of Captain Kidd’s buried loot. (Keep your eyes peeled—you never know what’s still out there!)
See the Devil’s Footprint, a mysterious boulder imprint said to bring good luck to anyone whose foot fits inside it. Spoiler: every foot fits.
Meet the fish that fed an entire industry—until it was banned! Discover the amazing story of the inedible menhaden and why it mattered so much.
What Makes This Experience Family-Friendly
Private & Personalized:
With a maximum of six guests, your family has the entire boat to yourselves.
All Ages Welcome:
We provide Coast Guard–approved infant, toddler, youth, and adult life jackets so everyone stays safe and comfortable.
Hands-On Fun:
Children 12 and under can help steer under the captain’s supervision and teens 13 and older can help raise the sails, take the helm, or simply enjoy spotting wildlife like ospreys and cormorants.
Educational & Inspiring:
Learn about Greenport’s shipbuilding legacy, the boat’s century-old story, and the basics of wind, navigation, and sailing—an experience that turns curiosity into wonder.
Book your private North Fork family activity today and set sail on an adventure your kids will remember forever.