Some of the best days in the Saling East End happen on the water.
You don’t need your own boat to go sailing in the Saling East End here. All season long, public day sails, sunset cruises, and private charters set out from the harbors of the North Fork, the Hamptons, Shelter Island, and Montauk.
Some people want to help with the sails. Others just want to sit back and enjoy the ride.
Did You Know?
In the 1800s, Sag Harbor was one of the busiest whaling ports in America, sending ships on voyages that could last two to four years as they circled the globe. Today those same harbors are still some of the easiest places to get out on the water.
If you want a sunset cruise or a private charter, there are a few ways to get out on the water.
Choose Your Adventure
Day Sails & Sunset Cruises
Some trips sell seats by the ticket, while others let you book the whole boat.
Private Yacht Charters
Charter a crewed motor yacht for a celebration, a proposal, or a day exploring the bays in style.
Where to Set Sail
The East End’s sailing scene clusters around a handful of historic harbors, each with its own character.
Greenport
Greenport Harbor is one of the main places to leave from if you’re heading toward Shelter Island or Peconic Bay.
Shelter Island
Set between the two forks in Shelter Island Sound, the island is both a destination and a departure point. Several charter fleets are based here, and the protected water around Dering Harbor makes an easy, scenic first stop under sail.
Sag Harbor
With its maritime history and protected waters, Sag Harbor is a natural place to start a sunset sail or a harbor cruise.
Montauk
Ocean cruises and eco-tours provide another unique way to experience the easternmost point of Long Island from the water.
Under Sail: Day Sails & Sunset Cruises
These trips run under sail: schooners, catboats, and catamarans. Some sell tickets by the seat, the easiest and least expensive way aboard; others charter the whole boat for your group. Several do both.
Greenport – Sail NoFo offers private afternoon and sunset sails around Greenport and Shelter Island from Friday through Sunday, with longer overnight trips midweek.
Layla Sailing, a women-owned charter crewed entirely by women, keeps trips to six guests and runs a handful of special pop-up sails and one-time experiences throughout the season.
East End Charters sails two vessels from May through September: the 72-foot schooner Bonnie Lynn, which carries up to 32 guests and also sells tickets to two-hour public sails several times a week, and the 57-foot wooden ketch Surprise, a private trip for up to six.
Greenport & Shelter Island – Sail Selina NY runs short sails on Selina, a wooden catboat built in Greenport in 1926, for up to six guests at a time.
Sag Harbor – SailHamptons runs a Coast Guard certified sailing fleet led by the 74-foot Bermudian schooner Luna, which takes up to 41 guests, alongside the mahogany trimaran Cosmos. Both private charters and ticketed sails are available.
Montauk – Sailing Montauk runs seasonal sails aboard Mon Tiki out of Montauk Harbor, including sunset trips.
Motor Yacht Charters
If you would rather have speed, space, and a cabin than canvas overhead, these fleets charter crewed motor yachts by the half or full day, each with a licensed captain.
Shelter Island – Charters in The Hamptons, family-run since 2016, keeps a fleet of more than 20 powerboats, including 57- and 62-foot Pershing yachts, with pickups at Greenport, Sag Harbor, and Montauk.
Sag Harbor – Yacht Hampton runs one of the area’s largest fleets, from intimate day boats to overnight yachts, for sunset cruises and dock-and-dine outings, departing Sag Harbor, East Hampton, and Montauk.
The Hamptons – East End Yachts offers premium crewed yacht charters across the Hamptons. Most book by the half or full day and can be tailored to birthdays, proposals, corporate outings, or simply a day exploring the bays.
Local Tip
Sunset sails are among the East End’s most popular experiences during the summer season, so booking in advance is recommended.
Make a Day of It or an Overnight
The East End rewards a full day on the water but the region really opens up when you stay the night. Trading the drive home for a sunset dinner, a quiet morning harbor, and a second day to explore is what turns a good outing into a true getaway.
Greenport
Board a morning or sunset sail out of Greenport Harbor, then wander the village’s shops and waterfront restaurants. Stay the night at a harbor inn and catch the ferry over to Shelter Island in the morning.
Sag Harbor
Take a sunset cruise from Sag Harbor, then trade the dock for dinner in one of the East End’s most storied villages. Book a room in town and spend the next day among its whaling history, galleries, and beaches.
Shelter Island
Sail into Dering Harbor and enjoy lunch overlooking the water, then let the island slow you down, an overnight at a historic inn and a quiet morning by the water before the day-trippers arrive.
Montauk
Set out on an afternoon or sunset sail from Montauk Harbor, explore the town’s restaurants and beaches, and make it an overnight so you can end the day watching the sun drop from Montauk Point.
Make It an Overnight
Whichever corner of the East End you explore, there’s a place to wake up nearby and a night here is what makes the trip worth extending. Explore where to stay across the East End →
Before You Go
- Reserve sailing excursions and charters well in advance during the summer season.
- Check wind and weather conditions before heading out.
- Confirm your departure marina and parking ahead of time, especially in Sag Harbor and Greenport.
- Wear appropriate footwear and sun protection.
- No experience is needed for most cruises and charters, your captain and crew handle everything.
Experience the East End Under Sail
However you spend it, a first day sail, a lazy sunset cruise, a private charter with friends, a day under sail has a way of pulling you back. Slow down, breathe in the salt air, and let the harbor you set out from become the reason you return.
Rather get on the water yourself? Read Explore the East End by Water for kayaking, paddleboarding, and surfing across the East End.