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Private sailing trips in the Thimble Islands, Branford, CT

Overview
PLEASE NOTE: RATES ARE BASED FOR UP TO 4 PEOPLE.
Please contact us for larger groups.
Discovering and sailing thru the Thimble Islands is a unique experience, 300 islands to look at from a sailing yacht giving you plenty of time to take pictures.

The Thimble islands are one of those well kept secrets not yet well known from the crowds which gives its charm and serenity.

On our approx. 2.5 hour cruises, we can anchor and swim in total safety and calm waters. If you wish to add another hour or two, please let us know.
Start times are 10am - 2pm - 5pm every day.
City: Connecticut
Fri 20 Sep
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You can choose the date already on the booking website
Starting at $640.00
Fri 20 Sep
Starting at $640.00
Make a reservation
What's Included
Soda/Pop
Bottled water
Additional Info
  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Hand sanitiser available to travellers and staff
  • Gear/equipment sanitised between use
  • Regular temperature checks for staff
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (6)
nrichard70
Jul 2018
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.
dcan2017
Jul 2017
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!
Response from Host
Jul 2017
Merci beaucoup Deborah!!
Tim K
Jun 2017
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!
Response from Host
Jun 2017
Thank you Tim, you were amazing and very easy going guests!! Until next time...Cuba? šŸ˜Ž

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