Sail Aboard Endeavor

Nantucket’s Oldest Sailing Charter

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Sail with Experience

The Endeavor, a United States Coast Guard certified vessel, is the longest operating sailing charter on Nantucket. Captain James Genthner, licensed by the United States Coast Guard, has over 40 years of experience sailing the pristine waters of Nantucket.

Captain Jim offers private charters and per-person fare sailing trips around the waters of Nantucket Island. He can acquaint you with Nantucket's maritime history and sights along the waterfront. Sailing excursions are offered from May through October.

Novice and experienced sailors of all ages can help the crew set sail or simply relax and enjoy the ride. Guests are welcome to bring aboard refreshments. Captain Jim built Endeavor, and if you wish, he will share his knowledge of traditional boat building. Captain Jim and Sue Genthner live on Nantucket year-round with their children Lisa and James.

Discover the Authentic Nantucket

The picturesque waters and shores of Nantucket Island are seen from the deck of the Endeavor. Enjoy one of our daytime or sunset sails.

 
 
 
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DIP YOUR TOES IN • 1 ½ HOUR

Daytime Sail

Enjoy the views as we sail past Brant point lighthouse on a morning or afternoon sail. Captain Jim is happy to share island history and tales from his four decades of sailing in Nantucket Sound.

 
 
EVENING ADVENTURE • 1 ½ HOUR

Sunset Sail

Our Sunset Sail is the best way to take in one of Nantucket’s spectacular sunsets! Start your night out with a peaceful cruise, then check out one of downtown’s many award-winning restaurants.

© Liza Gershman

© Liza Gershman

 
 
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GROUPS + CUSTOM EVENTS

Private Charters

Private Charters are the perfect way for family and friends to spend time on the water together. We can help you celebrate that special occasion or provide a unique venue for photos or corporate meetings.

IDEAL FOR:

  • Family reunions

  • Proposals + elopements
    (yes, you can get married aboard Endeavor!)

  • Photoshoots – families, couples, apparel, products

  • Bachelor & bachelorette parties

  • Birthdays, anniversaries, graduations

  • Plus, it’s the only way to bring your pup aboard!

 

What People are Saying

ENGAGEMENT

“Sixteen years ago, my husband chartered this boat to ask me to marry him. It was amazing! Now...for our 15th anniversary, we are going back out on the boat. This boat (and the island) is amazing!”

– SHANNON

WONDERFUL TIME

“We chartered the boat and took along our four grandkids ranging from 5-9 years old and we all enjoyed the sail… Sailing on the Endeavor is one of Nantucket’s greatest offerings and gives you a great “ offshore” perspective. Trust me, you will love it!

– PATTI

BEAUTIFUL NIGHT

“This was the best sailing trip! Great sunset, Captain Jim was fantastic – he knew lots of history of the island and told great stories. Perfect weather and incredible sunset!”

– SANDY

READ MORE REVIEWS ON TRIPADVISOR
 
 
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Find Us

We’re conveniently located right on Straight Wharf, just steps from Main Street.

Slip #1015
Straight Wharf
Nantucket, MA 02554

(508) 228.5585
endeavorsailing@gmail.com