Rental Boats

All boats will be captained by a USCG licensed captain.

Bareboat Sailboat Rentals in the Hamptons 

Want a bareboat sailboat rental in the Hamptons, just you and the boat? You are in the right place. At Sag Harbor Sailing, qualified sailors can rent a 23-foot Pearson Ensign and sail it themselves. No captain, no set route. Drive in, park for the day or overnight, take the helm, and pick your own destination on the protected East End bays. Nowhere else in the Hamptons makes self-skippering this easy. 

The first question most people ask is simple.

Am I allowed to take a boat out on my own? Here is the honest answer. You do not need a formal license, but you do need real skill. To rent without a captain, you should be able to rig the boat, leave the dock, sail a course, and return to the dock without help. That is the bar. Before your first solo rental, our staff confirm you are comfortable handling the Ensign. It is a quick, friendly check, not a test designed to trip you up.

If you trained elsewhere or earned an ASA certification, even better. ASA 101 is a great way to reach this level, though it is not strictly required. What matters is that you can handle the boat safely and confidently on your own. If you are close but not quite there, we will point you to the next step rather than send you out unprepared. Want the full rundown on handling the boat solo? See our guide to the 23-foot Pearson Ensign bareboat rental for specs and what to expect on your own.

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Now the boat. You sail a 23-foot Pearson Ensign, a stable, forgiving keelboat that is easy to read. It seats up to six people and has a head on board. The deep, weighted keel keeps it steady, even when the breeze picks up. It is a clean, simple boat to single-hand or sail with a small crew. Every rental includes life jackets and basic safety gear. You bring sunscreen, a hat, water, and soft-soled shoes for the deck.

Here is what sets a Sag Harbor rental apart. You drive right to the dock at 51 Pine Neck Avenue and park for the day, or even overnight. Load your gear, step aboard, and go. There is no marina shuffle and no waiting on a crew. When you are done, you bring the boat back to the same dock. It is about as simple as self-skippering in the Hamptons gets.

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Where can you go?

That depends on your time and the wind. In a half day, you can sail the calm water around Shelter Island or trace the North Haven shoreline. A full day opens up Peconic Bay and the wider Twin Forks. You might pass Cedar Point Lighthouse in Northwest Harbor or the wooded edge of Mashomack Preserve on Shelter Island. Because you stay on sheltered bays, the water is calmer than the open Sound or ocean. That makes solo sailing a lot more relaxing. 

The best part of going without a captain is the freedom. You set the pace and the plan. Drop anchor in a quiet cove for lunch. Chase the wind across the bay. Turn back early or stay out until the light fades. No one is rushing you to a schedule. It is your boat for the whole day.

Let's talk price. Bareboat rentals start at $475, plus fuel and any extras. Full payment is due when you book. We will give you a clear all-in total and explain the security deposit before you sail, so nothing is a surprise at the dock. Call (631) 725-5100 for current rates and deposit details. If you plan to sail often, the Commodores Club lowers your per-trip cost for the whole season.

Not ready to solo just yet?

No problem. You have a few good options. Book a captained sailing charter and let our captain do the work while you learn the boat. Take a private lesson or earn your ASA 101 first. Or join the Commodores Club once you are cleared to self-skipper. There is a path for every skill level, and you can move up at your own pace.

When you arrive, we have the boat fueled and ready at the dock. A short walk-through covers the safety gear and the day's wind and weather. Then the bay is yours. Ready to sail on your own? Call (631) 725-5100 or check availability online. Summer dates fill fast, so book ahead. 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.

 

 

FAQS

Pearson Sailboat Without Captain

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23' Pearson Ensign Without Captain - Natasha Image 1
23' Pearson Ensign Without Captain - Natasha Image 2
23' Pearson Ensign Without Captain - Natasha Image 3

23' Pearson Ensign Without Captain - Natasha

Location Sag Harbor
$475 + Fuel, Staff & Gratuity
Length 23
Capacity 6
Crew No Captain
Trip Type Day
More Info

All boats will be captained by a USCG licensed captain.

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