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Sag Harbor Sailing Lessons and Rental

How This Sag Harbor NY Company First Set Sail

Sag Harbor Sailing opened its doors in 1997 when owner Jim Tompkins began with a few boats at the marina in Sag Harbor and the idea to offer boating customers a chance to sail themselves. Now, two decades later, his son Mark and co-owner Bob Sullivan, report having had hundreds of students graduate from Sag Harbor Sailing’s award-winning educational sailing programs, thanks to Jim’s original vision.

Sag Harbor turns guests into sailors

Students 8 to 80 Have Sailed Through Their Sag Harbor Sailing Programs

Bob Sullivan’s students of all ages have graduated to solo sailing from instruction they’ve received from the school that today is relied upon by almost 500 companies to perform team-building competitions. On the non-corporate side, Sag Harbor sailing is host to a sea of summer family gatherings planned around a sailing experience.

Opportunities are available for kids and adults to sail

Sag Harbor Sailing Offerings

If you’re thinking about having an experience on the water away from the hustle of New York City or wherever you call home, then a Sag Harbor Sailing adventure may be just what Captain Bob ordered. Great for a family outing or gathering with friends, sailing around sunset beach, to Peconic Bay or Shelter Island gives the occasion a beautiful backdrop that is the perfect setting for blissful bonding.

Take dad, the wife, the kids out for a sail


Sailing around The glorious Hamptons

How to Navigate the Best Sailing Trip

Yes, it can be overwhelming, as there are a variety of sailboats and outings to choose from. That’s why Captains Bob and Mark are on hand to steer your party towards the best sailing experience possible. Take a look at some of your options and talk it over with the trip masters.

A seasoned instructor makes a sailboat feel like home

Sailboat Rentals

Below are some of the offerings for boat rentals or water rental equipment:

  • Rental for Pearson Ensign – Enjoy your sailing adventure with this keelboat that has an outboard engine and room for 6 passengers. With this rig, you can easily explore the beauty of the shorelines of Long Island, sail to Shelter Island, explore Peconic Bay or any of the fabulous destinations along the water. As with all boats, you can choose to add a captain while you take in the fresh air and scenery.
  • Rental for Catalina Sloop 27’ – This boat rental is a perfect option for your more ambitious adventures, with one stateroom and room for six passengers. There is a range and icebox, cooking utensils and serving ware, plus a private head containing cold water for a shower. The helm is well-equipped with a complete instrumentation that includes a depth finder. For Catalina Sloop 27′, you can also opt to add a captain as your navigation crew.
  • Rental for Catalina Sloop 34’ – Bigger is simply better for larger groups. The 34′ Catalina features 2 staterooms and its helm is well-equipped with GPS, auto-pilot, and instrumentation.

What size sailboat works for your trip?

Come to Sag Harbor NY for Sailing Lessons Too

If you want more information about how you can learn about proper sailing, we’ve listed some of the courses most popular with our guests.

  • Private Lesson – 4 people can participate in this private session that focuses on the basics of proper sailing, navigation of a boat or yacht. Pro instructors are the only ones conducting private lessons for this training.
  • ASA Course for Beginners (ASA 101) – Graduates from this course are able to sail a 23’ boat in length in light to even moderate winds and sea weather conditions without supervision. You may want to enroll in this Sag Harbor course if you’re looking to have a perfect sailing experience with a captain along to better enjoy a charter with your loved ones and friends.
  • ASA Certification Course for Intermediate Level (ASA 103) – Successful captain graduates from this course can safely cruise in both regional and local waters as both crew and skippers on an auxiliary powered 27’ sailboat, in modest winds and weather conditions. It’s an accomplishment not to be modest about and one that will enhance every charter experience on the water by a nautical mile.

Certify to sail in mild or wild weather conditions


It may take more than one trip to get a high level certification

More Hamptons Charters

There are so many activities to enjoy in these waters in and around Sag Harbor, including sunset boat charters, sails to swimming spots and tours of the region’s landmarks, dining cruises, and a whole lot of fishing excursions to East Hampton, Long Island Sound and Montauk Bay just to name a few.

Sail in some of the most beautiful waters in the country


Add a dining excursion or two to your trip

Once you get into the swim of things with your friends or family, you will be able to navigate your Hampton’s cruising options, with the help of the many friendly boat rental owners instructors, captains and overall staff at the ready to help mark your summer with magnificent memorable sails.

Kids jump at the chance to jump into the Atlantic


Sag Harbor, the best place to sail in the country

For more information about sailboats, yachts, and services, visit the Yacht Hampton website.

Copyright 2021