You don’t need to own a yacht to spend a day on the water in the Hamptons. With our Hamptons sailboat rentals, you can step aboard a classic 23-foot Pearson Ensign. Sail the calm bays around Sag Harbor with a captain at the helm, or take the tiller yourself. Sag Harbor Sailing is a family-run, ASA-accredited operation. We’ve been here since 1997. We keep it simple. You get a well-kept fleet, flat pricing, and room for up to six people on every boat. So whether you’d like a captain aboard or you’d rather sail it yourself, there’s a boat ready for you.

Our Sailboat Fleet

Our fleet is built around the 23-foot Pearson Ensign. It’s a classic keelboat: stable, roomy, and easy to enjoy. You don’t have to sail often to feel at home aboard one. Each boat seats up to six people. That makes it a good fit for a couple, a family, or a small group of friends.

These are real sailboats, not motor boats or party boats. You’ll feel the wind and hear the water. You’ll also see Sag Harbor from a view most visitors never get. Boats in our fleet include Natasha and Little Julf. Guests often tell us how well-kept they are.

You can view each boat and book it directly. Choose the 23' Pearson Ensign rental with a captain aboard, or rent without a captain and take the helm yourself. Every boat is owned and cared for by our team. Our captains are licensed by the U.S. Coast Guard.

With a Captain or Without

One thing sets us apart from the big charter yachts in the Hamptons: choice. You can rent the same 23-foot Pearson Ensign two ways.

With a captain, a licensed skipper handles the boat. You relax, take photos, or pick up a few sailing tips at your own pace. This is the easy option for first-timers, families with kids, and anyone who just wants to enjoy the ride. Our captains know these waters, so they’ll find the calm, scenic spots.

Without a captain, you rent the Ensign on your own. You set your own course around the bay. Both options come at the same flat day rate. So you can pick the experience you want, not the one that fits a budget. Not sure which suits you? Just ask when you book, and we’ll point you the right way.

Who Comes Aboard

Our Hamptons sailboat rentals work for all kinds of days out. Couples book a quiet afternoon on the bay. Parents bring kids who light up the moment they help steer. Friends split a boat for a relaxed group outing. First-time sailors ride along with a captain. Lifelong sailors take the helm and go.

Because the Pearson Ensign holds up to six, it suits small groups better than big parties. If you want an intimate day on a real sailboat, this is it. Planning a larger team outing instead? Ask us about our corporate sailing events.

How Booking Works

Booking is done online, and most boats can be reserved instantly. You pick your boat, your date, and how long you’d like to be out. We offer two trip lengths. Choose a 3 to 4 hour sail, or a longer 6 to 8 hour day.

Day rentals of the 23-foot Pearson Ensign start at $475, plus fuel, staff, and gratuity. That add-on covers the fuel you use, the crew’s time, and a tip for good service. It’s worth factoring into your budget, and we’ll walk you through it when you book.

We take cash, credit cards, debit cards, and mobile payments like Apple Pay and Google Pay. Appointments are recommended, since dates fill up fast on summer weekends.

Weather happens. If conditions keep us off the water, your booking earns a rain-date credit. It’s good for 28 months, so you won’t lose your day. Booking early has a perk too. From January through March, you can reserve with a 50% deposit.

Where You’ll Sail

Sag Harbor sits on some of the calm, scenic water of the East End of Long Island. Most sails stay in the protected bays around the village. The wind is steady and the water is gentle. It’s a relaxed place to learn, or to simply unwind.

From the water you’ll take in Shelter Island, the North Haven shoreline, and the historic Sag Harbor waterfront. Our booking options also include trips toward Montauk, for those who want to range a little farther. These are bays and harbors, not the open ocean. That’s part of what makes a day here feel easy rather than rough.

Wherever you go, you’re sailing the same East End waters that have drawn boaters to the Hamptons for generations.

WATER TOY OPTIONS

We Include with your Rental:
Life Jackets, Noodles

Optional Items Are:
Snorkel, Fishing Gear, Seabobs, Sun Chill Floating Lily Pad, Water Skiing (2 hours), Wake Boarding (2 hours) & Tubing (2 hours)

Save With the Commodores Club

Planning to come back? Our Commodores Club is worth a look. Members who sail more than three times in a season earn seasonal savings. That adds up quickly if sailing becomes your summer habit. It’s a simple way for regulars, families, and returning renters to get more time on the water for less. The club runs out of our home base at the Yacht Hampton Boating Center on Pine Neck Avenue in Sag Harbor. Ask us about joining when you book your next sail.

Want to learn the ropes before you rent on your own? Our sailing lessons are a good place to start.

Ready for a Day on the Water?

A sailboat rental in Sag Harbor is one of the simplest ways to enjoy a Hamptons summer. Pick your boat, choose with or without a captain, and we’ll take care of the rest. Call or text us at (631) 725-5100 with a question, or to lock in your date. You can also book online any time. Our season fills up quickly, so the sooner you reach out, the better.

SAILBOAT RENTALS IN SAG HARBOR — OUR FLEET