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Endeavor Sailing Excursions
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Traveler Overview
  • Excellent91%
  • Very good4%
  • Average1%
  • Poor3%
  • Terrible1%
Travelers talk about
“captain jim”(21 reviews)
“sunset cruise”(6 reviews)
“his son”(3 reviews)
The Endeavor has been offering sailing excursions in Nantucket Sound for 30 years. Voted by Yankee Magazine as "Best in New England", the Endeavor operates from May-October. Per person fares start at $45.00. Private charters are available for an...more
Slip #1015, Straight Wharf, Nantucket, MA 02554
+1 508-228-5585
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Reviews (62)
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All reviews captain jim sunset cruise his son family run highlight of our trip great fun sails sailboat sailed skiing crew island stories jetties whales boats whaling
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1 - 10 of 62 reviews
Reviewed October 11, 2018 via mobile

Captain Jimmy is a wonderful, jolly, and salty sailor! Couldn’t have asked for a better Captain. BUT Ben was the star of the show! One look at Ben and you just know, you are safe in his hands. His eyes are like the ocean, one...More

Date of experience: October 2018
4  Thank djnyy2
Reviewed October 10, 2018 via mobile

Had a great time on the Endeavor sunset cruise. The captain and staff were helpful. The ability to bring your own wine/ snacks was a real plus. The highlight of our visit to Nantucket

Date of experience: September 2018
Thank Steve S
Reviewed October 8, 2018

Took a private sail with four others on my first sail ever. Crew was superb and very welcoming and easy to talk to. I learned some things and got to participate in controlling the boat. The boat was hand built by the captain which I...More

Date of experience: September 2018
Thank Getaway817942
Reviewed August 31, 2018 via mobile

Our only other sailing experience is on the larger sailboat in Bar Harbor. Both are fun. This is a smaller boat. I think it is a 200 year old commercial fishing design. Totally different than motor boating. Hard to get a feel for what it...More

Date of experience: August 2018
Thank w945106
Reviewed August 28, 2018

If you go with the tour, you are going to be cramped. If you rent on your own, you have enough space, but the 1.5 hr tour is really just a straight line sail out past a few jetties and back. Nothing to see. You...More

Date of experience: July 2018
Thank Scott M
endeavorsailing, Owner at Endeavor Sailing Excursions, responded to this reviewResponded October 5, 2018

Hi Scott, Our sailing route is dependent on the wind direction so our guests have the most time under sail and not motoring. You went past Brant Point Lighthouse, the homes and beaches along the waterfront, Coatue which is conservation land and great bird habitat...More

Reviewed August 27, 2018

We had pretty high expectations after seeing the Endeavor glorified on a blog that one of us follows, and then reading so many positive reviews here. Frankly we were underwhelmed by the whole experience. We appreciate that it's small, family-run and low key, but it...More

Date of experience: August 2018
Thank Nina_and_James
Reviewed August 27, 2018

We took the sunset trip. We reserved it about a month ahead of time. You are not guaranteed a sunset of course but this is a really great and fun way to see the island and experience the ocean. The sailboat has an older feel...More

Date of experience: August 2018
Thank cq94
Reviewed August 5, 2018

My family recently went out on the Endeavor on our Nantucket trip and had a wonderful time. Not only was the boat ride itself spectacular but Captain Jim and his daughter were so sweet. They were very accommodating and talkative, giving us great information about...More

Date of experience: July 2018
Thank lembrichtaylor
Reviewed July 22, 2018 via mobile

We have sailed on the Endeavor many times but our last sail on July 14, 2018 may have been our best to date . Our family sailed with Captain Jim and his daughter, Lisa, to celebrate my husband’s birthday. We chartered the boat and took...More

Date of experience: July 2018
Thank PattiGram
Reviewed July 4, 2018 via mobile

We heard from a number of visitors that the Endeavor Sailing excursion was among the most fun activities on Nantucket. We were not disappointed; Captain Jim was super knowledgeable and provided some great commentary about Nantucket and sailing. One of the few reasonably priced excursions...More

Date of experience: July 2018
Thank 237mohamede
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