How many guests can come aboard?

Up to six guests sail on the 23-foot Pearson Ensign, plus your captain. The smaller group keeps the day relaxed and personal. Call (631) 725-5100 to book your charter.

How much does a sailing charter cost compared with a crewed yacht?

Our charters start at $475 plus fuel, staff and gratuity, with the captain included. Crewed luxury yachts here often price by quote and run well over a thousand dollars for a few hours. You get real sailing for far less.

Where can we go on a half day versus a full day?

A half day reaches Shelter Island and the North Haven shoreline. A full day opens up Peconic Bay and the Twin Forks. Your captain sets the route based on the wind. All of it stays on calm, protected bays.

Do you run sunset charters?

Yes. We offer sunset charters through the season, from mid-May to the end of September. It is a quiet, scenic way to end the day on the water. Call (631) 725-5100 to check sunset dates.

What is your weather and cancellation policy?

We do not sail in rain or during a small craft advisory, and we usually decide about two hours before your trip. If we cancel for weather, you get a rain-date credit good for 28 months. Your safety always comes first.

Hamptons Sailing Charters from Sag Harbor

Looking for Hamptons sailing charters that are about the sailing, not just the party? Come aboard with us. At Sag Harbor Sailing, a charter means real time under sail on a 23-foot Pearson Ensign, with a USCG-licensed captain at your side. No giant party boat, no engine droning the whole way. Just wind, water, and the quiet of the protected East End bays. It is an intimate day on the water for up to six guests.

So what is a charter with us, exactly? You book the boat and a captain for a half day or a full day. Your captain handles the sailing, so you can relax. Or you can take the helm and learn as you go. The choice is yours. The 23-foot Pearson Ensign is a stable, classic keelboat. It seats up to six people and has a head on board. We also run sunset charters through the season, when the light over the bay is at its best.

Types of Charters

A typical charter is easy and unhurried. You arrive at our dock at 51 Pine Neck Avenue. Your captain greets you, runs a quick safety check, and helps everyone aboard. Then you head out of the harbor and raise the sails. From there it is wind and water for the rest of your trip. You can help trim the sails, take a turn at the helm, or simply sit back and watch the shoreline slide by. Our Hamptons sailing charters stay on protected water the whole way.

The Boat and Your Captain

The boat is part of the appeal. The Pearson Ensign is a classic American daysailer with a deep, weighted keel, so it stays steady even in a fresh breeze. The open cockpit seats your whole group within easy talking distance. A small cabin holds a head, so you can stay out for a full day in comfort. It is the kind of boat that makes new sailors feel safe and lets experienced hands enjoy a clean, simple sail.

Where will you sail?

It depends on how long you are out. In a half day, you can cruise the calm water around Shelter Island or follow the North Haven shoreline. A full day opens up Peconic Bay and the wider Twin Forks. Your captain knows these waters and picks the route that fits the wind and your group. When should you go? Mornings bring the calmest water and lightest wind, which suits families and first-timers. Afternoons fill in with a steady sea breeze for a livelier sail. Evenings settle down again for the sunset trips. Tell us what you want and we will point you to the right slot. Along the way you might pass Cedar Point Lighthouse in Northwest Harbor, the wooded shoreline of Mashomack Preserve on Shelter Island, or the quiet beaches of North Haven. You stay on sheltered bays the whole time, so you skip the open-ocean swell.

Policies

Deposits

Full payment is due at booking. Dates/times can be changed when you notify us in writing of your request >90 days before sailing date. If booking in January, February or March we allow 50% deposit these months. Kindly text any request at time of booking.

Weather & Cancellations

We have a no-rain and small craft advisory policy so we do not set sail if it is currently raining or rain is imminent in the forecast. We also obviously care about your safety, so we will not set sail in inclement weather and during any small craft advisory. We will generally make those decisions 2-hours before sailing time. If our captain decides not to set sail that day, due to rain or if a small craft advisory is in effect, you will have the option to receive a rain date for a period of 28 months. This allows you 3 summer seasons to reschedule. We will apply your payment and you will receive that credit to sail again within the next 28 months.

Once a client books a boat we notify all subsequent inquiries that “the boat is taken and unavailable”. For this reason we do not offer any refund on cancellations. If you cancel a reservation up to 90 days before your sail date, we do allow a no-cost change of date. Inclement weather as stated above is the sole reason for any cancellation.

Please click the “Booking Calendar” link above, check availability, and book away!

Cleaning Fees

Any vessel returned that requires additional clean up will be charged $50.00.

Late Fees

Any vessel returning to dock after the agreed upon return time will be charged $75 and charged $75 again for every hour thereafter.

How to Book a Charter

Who charters with us? Couples wanting a quiet afternoon. Families with kids. Small groups marking a birthday or an anniversary. Anyone who would rather feel the boat move under sail than ride a crowded motor yacht. Because the group is capped at six, it never feels packed. You get room to spread out and a captain who actually talks to you. Companies book us for small team outings, including Fortune 500 groups that run sailing regattas with us. A charter also suits a proposal, a family reunion, or a first-timer who wants to try sailing before signing up for a full course.

Sag-Harbor-Sailing-Rentals_KEY_luffing-the-jib

Let's talk price, because most competitors won't. Charters start at our day rate of $475 plus fuel, staff and gratuity. That add-on covers your captain and the boat's running costs. We will give you a clear all-in total when you book, so there is no surprise at the dock. Call (631) 725-5100 for current charter rates and to check open dates. If you plan to sail more than a few times, ask about the Commodores Club for season-long savings.

What is included? You get the boat, your USCG-licensed captain, and life jackets and safety gear. Bring a cooler, sunscreen, a hat, and soft-soled shoes for the deck. Leave the heavy planning to us. We sail out of the Yacht Hampton Boating Center at 51 Pine Neck Avenue in Sag Harbor, from mid-May through the end of September.

Booking is simple. Pick a half day or a full day, choose your date, and we confirm your captain and your all-in total. Full payment is due at booking. You can change your date at no cost up to 90 days before you sail.

Ready to book? A captained sailboat charter from Sag Harbor is one of the best ways to see the Hamptons from the water. Call (631) 725-5100 or check availability online. Summer weekends book up early, so reserve ahead. We will help you plan the perfect day on the bay.

Water Toys & Gear

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)

Spend a Day on the Water

A Hamptons sailing charter is one of the simplest, most relaxing ways to enjoy summer out here. Pick a half-day or full-day, choose a captain or skipper yourself, and we’ll take care of the rest. Call or text us at (631) 725-5100 to ask a question or book your sail. We’d love to show you the Hamptons from the water.