Thimble Islands Private Sailing Trips: Serene Exploration
8 Ratings
New London
Embark on a serene exploration of the Thimble Islands with our private sailing trips. Discover 300 islands, take stunning pictures, and enjoy a swim in calm waters. Book now!
Duration: 3 hours
Cancellation: 1 day learn more
  • 55 Goodsell Point Rd - We offer a wide range of sailing cruises in various locations. Charters are all captained. Sailing time vary from as little as 2 hours to full day charters, overnight and adventure sailing trips. Destination and locations are: Branford, CT and the Thimble Islands.
    Sailing instruction can be provided as well on your boat or ours. We also propose charters in the Mediterranean on 45’ luxury catamarans. Call for details.
What's Included
  • Unlimited carbonated beverages
  • Complimentary bottled water
Additional Information

Please specify the number of attendees and preferred time slot: 10am, 2pm, or 4.30pm. Get in touch with us for groups of more than 4 but less than 10 people.

We can arrange for extended trips and larger groups as per your request.
Embarking on a sailing journey through the Thimble Islands is a truly unique experience. There are 300 islands to admire from the comfort of a sailboat, providing ample opportunities for capturing splendid photographs.

The Thimble islands, still relatively undiscovered by tourist swarms, retain a quaint charm and tranquillity.

Our sailing adventure is typically 2.5-3 hours in duration during which we can dock and swim in completely serene and safe waters. If you would like to extend your sail by an hour or two, just let us know.

260 Pequot Ave
Pequot Avenue
Thamesport Marina - Slip S44 (end of South dock)
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(8 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Sep 20, 2023
Fantastic sailing experience - While visiting family in Connecticut I decided to take them all on this excursion. My mother and father in law are retired sailers who haven’t been on a boat in years and everyone could not have had a better time.
Review provided by Viator
Jul 27, 2023
Fabulous Sail - Capt. Eric is terrific, highly engaging and an excellent sailor. We will be back again soon. Highly recommend
Review provided by Viator
Jul 30, 2022
Wonderful Memories! - We recently chartered a sail through the Thimble Islands with Eric on his beautiful sailboat Nomade to scatter my husband’s ashes on the Sound with our friends and family. Eric made the day truly magical. The event was everything I could have asked for and more. I can’t say enough about the ease of communication coordinating our event with him as well as the entire afternoon. He was so accommodating, made us all feel like family and gave us a wonderful memory - and sail - that will stay with us forever. Nomade was the perfect venue for our event and Eric was the perfect host, whom we all now consider a friend. I am forever grateful.
Review provided by Tripadvisor
Aug 29, 2021
Perfect sail - Everything was perfect, the time the communication, boat was very clean, the captain was friendly and informative. The weather happened to be great too. We had a great time! Thanks Capitan Eric!!
Review provided by Tripadvisor
Aug 4, 2019
Overnight Sail in Thimble Islands - I emailed Eric with a unique request asking if our group of 2 couples could do an evening sail with dinner on the boat and stay overnight. I fully expected that my idea would be too expensive to make a reality, but Eric responded quickly, and offered a plan to sail to the Thimble Islands, including allowing us to stay alone on his beautiful boat overnight! We moored in a secluded cove at dusk and he guided us through parts of the boat we’d need before riding off in the dinghy to stay with friends. We thoroughly enjoyed Eric’s company but it was very exciting to feel like the boat was ours for a night. It was like a little slice of heaven: eating dinner under the stars listening to music, watching the sun rise, and swimming in the cove in the morning. The whole experience felt serendipitous and we all left wishing for more. Couldn’t recommend sail-works more highly.
Review provided by Tripadvisor
Jul 12, 2018
Awesome afternoon! - We chartered the sailboat as part of a company team building event. Great way to get away from the office and bond with colleagues. Lots of laughs, food, and swimming in the Thimble Islands, as well as a beautiful sunset and attentive Captain and crew. Would definitely recommend to others.
Review provided by Tripadvisor
Jul 19, 2017
Great Day - To celebrate my brother's retirement, I treated him and his wife to a day of sailing. Luckily, they asked me to join them! Eric was a gracious host and helpful every step of the way--from arranging the gift certificate to choosing a convenient date. As an inexperienced sailor, I especially appreciated his calm and steady manner and his patience and assistance on board. My brother had a great time talking with the captain about technical matters, and my sister-in-law and I just sat back and enjoyed the beautiful sail into Thimble Islands. Sailing with Captain Treu was really just like sailing with a friend. We are looking forward to the next special event to celebrate at sea!
Review provided by Tripadvisor
Jun 20, 2017
Overnight sail to Sag Harber - After wisely postponing our trip due to weather Eric picked a two days we could really enjoy. We sailed out of Stonington CT and were included in every aspect of the sail from docking to raising sails. Except for my sister who just read her book and enjoyed the ride. Eric is an open book of sailing knowledge and willing to share with an easy going humorous personality. Our over night in Sag Harber was spent at a local Pub followed by a tour of the town. While sailing around the Shelter Islands on our trip back we enjoy the scenery and a great lunch. I had never had a Bagget before but now love them. I look forward to my next trip with Eric on a longer get away!
Review provided by Tripadvisor
Select Date and Tickets
up to 4 guests
April 2024