We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Endeavor Sailing Excursions

Slip #1015, Straight Wharf, Nantucket, MA 02554
+1 508-228-5585
Review Highlights
Great sunset sail!

We had a wonderful time with Captain Jim on his beautiful boat. We were celebrating a friends... read more

Reviewed 2 October 2016
via mobile
Great sail for a 7th grade trip

Captain Jim was outstanding for our 7th grade class trip. He explained the basics of sailing, some... read more

Reviewed 4 September 2016
Rick D
Milford, New Hampshire
via mobile
Read all 47 reviews
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
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 outing with family and friends or as an activity for corporate meetings. Reservations are suggested.
  • Excellent92%
  • Very good4%
  • Average0%
  • Poor2%
  • Terrible2%
Travellers talk about
“captain jim” (14 reviews)
“great sunset” (4 reviews)
Slip #1015, Straight Wharf, Nantucket, MA 02554
+1 508-228-5585
Write a Review
Reviews (47)
Traveller rating
Traveller type
Time of year

1 - 10 of 47 reviews

Reviewed 2 October 2016 via mobile

We had a wonderful time with Captain Jim on his beautiful boat. We were celebrating a friends birthday with a pre-dinner cocktail sail. We were able to bring lots of wine, cheese and laughs, and Captain Jim and his assistant tolerated our frequent photo taking...More

Thank RTTejas
Reviewed 4 September 2016 via mobile

Captain Jim was outstanding for our 7th grade class trip. He explained the basics of sailing, some geography of the island and the ocean and history of the area. Great interactions with the kids. Really well done.

Thank Rick D
Reviewed 29 August 2016

We booked Endeavor Sailing for a bachelorette group and I must admit, had some hesitations of the size of the boat since we were 13 girls! To our surprise, the boat felt as big as any other we've ever been on. Since we were floating...More

Thank heather b
Reviewed 15 August 2016

We were very much looking forward to a sail with this company. However, our flights were changed due to circumstances beyond our control and we would no longer be on the island in time for the sail. Unfortunately, due to the company's cancellation policy, we...More

4  Thank Explorer0912
Reviewed 6 June 2016

We all loved this excursion. Captain Jim was knowledgeable and entertaining. The kids got to help raise the sails and steer the boat. 1-½ hours was the right length of time for our kids. It was great.

2  Thank Linda B
Reviewed 23 May 2016

From start to finish this company was top notch. Sue was more than helpful and patient throughout the booking process. She helped me decide on which cruise and time would best fit our large family. Capt. Jim was great. He knows his island, is humble...More

2  Thank Shaktitourist
Reviewed 23 September 2015

Glorious sunny sail on Vintage Schooner with friendly and informative Captain at the helm. Guests were encouraged to help with the sails. Wonderful 2 hours on Nantucket Bay while learning of its history. Occasional sightings of whales or seals were mentioned, but none observed on...More

1  Thank MyWildIrishRose
Reviewed 23 September 2015

Beautiful way to see Nantucket shoreline from the sea, much as Whalers would have done 150 years ago. Guests are encouraged to work the sails and "lower the boom". May see a few seals or whales too, but not guaranteed. Just a great way to...More

Thank MyWildIrishRose
Reviewed 9 September 2015

Captain Jim was a great host. He was very generous in his replies to our "land lubber" questions and his explanations of the sport of sailing. We sailed just before sunset and throughout the cruise watched the sun slowly drop beyond the horizon - it...More

1  Thank djedushka
Reviewed 25 August 2015

We were a family of 5 (3 kids-10, 14, 17) and not only was the sail beautiful but the captain is a great guy to have a conversation with and knows so much about the island. We brought snacks and drinks, had a ball. On...More

1  Thank Hazel94111
Nearby Restaurants
Fog Island Cafe
440 reviews
.18 km away
433 reviews
.14 km away
The Nautilus
144 reviews
.16 km away
Straight Wharf
287 reviews
.04 km away
Nearby Attractions
Steamship Authority
61 reviews
.21 km away
Nantucket Atheneum
83 reviews
.25 km away
Nantucket Aquarium
27 reviews
.25 km away
Young's Bicycle Shop
117 reviews
.23 km away
Questions & Answers
Get quick answers from Endeavor Sailing Excursions staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines