Sailing Charters & Day Sails in the Hamptons

A sailing charter in the Hamptons doesn’t have to mean a giant party yacht or a four-figure bill. Sometimes the day you remember most is the quiet one: a classic sailboat, a small group, and a few hours of wind and open water. That’s what we do at Sag Harbor Sailing. Our Hamptons sailing charters take you out on a 23-foot Pearson Ensign, with a licensed captain at the helm or with you skippering yourself. Whether it’s a half-day escape or a full day on the bay, you get a real sailing experience, not a crowded booze cruise. Just you, your group of up to six, and the East End from the water.

A charter works for all kinds of days. Couples book a relaxed afternoon. Families bring the kids out for their first time under sail. Visitors get a look at the Hamptons that most people never see. However you spend it, it’s a calm, screen-free few hours on the bay.

Types of Charters

Our charters come in a few simple shapes, so you can pick the kind of day you want.

Day Sail w/ Captain

A captained day sail is the easiest option. A USCG-licensed captain handles the boat while you relax, take in the scenery, and sail without any of the work. It’s great for first-timers, families, and anyone who just wants to enjoy the ride. You can take a turn at the helm if you’d like, or sit back the whole time.

Half-Day Charter

A half-day charter is a few hours on the water. That’s usually enough to sail out, find a quiet spot, maybe swim or just drift, and come back relaxed. It’s a good fit for a morning or an afternoon.

Full-Day Charter

A full-day charter is for when you want to range farther, linger longer, and really settle into the rhythm of the water. It’s the better pick if you’d like to reach Montauk or spend the whole day out.

Custom Cruising w/o Captain

If you’d rather skipper yourself, ask us about a self-skippered, bareboat charter, available half-day or full-day. You set your own course around the bay. We’ll go over what’s needed to take the boat out on your own when you reach out.

Whatever you choose, you’re on the same 23-foot Pearson Ensign. What changes is how long you’re out and who’s at the helm.

If you’re new to sailing, they’ll happily explain what they’re doing and let you try the helm. If you’re experienced, they’ll trim for speed and let you enjoy the sail.

We’ve been sailing out of Sag Harbor since 1997, and we’re an ASA-accredited sailing school. So the people taking you out genuinely know how to sail, and how to teach it. Because the boat is small, the day feels personal. You’re not one of forty people on a big deck; it’s just your group and the captain.

Where You'll Sail

Most charters stay in the calm, protected bays around Sag Harbor, on the East End of Long Island. You’ll sail past Shelter Island and the North Haven shoreline, with the historic Sag Harbor waterfront behind you. The water here is gentler than the open ocean, which makes for an easy, scenic day.

On a full-day charter, there’s time to range a little farther. Trips toward Montauk are an option for those who want a longer sail east. Wherever you go, you’re on some of the prettiest water in the region, the same bays that have drawn sailors to the Hamptons for generations.

A charter is also a great way to see this stretch of coast the way it’s meant to be seen: slowly, from the deck of a sailboat, with no traffic and no rush.