The Best Boat Rentals Near Litchfield

Charter 36ft Sloop In Westbrook, Connecticut

We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

We had the absolute best day celebrating my birthday thanks to Captain Mark! From the moment we stepped on board, he made sure every detail was perfect. He had snacks and drinks ready for us, made sure everyone was comfortable, and truly went above and beyond to make the day special. He was so friendly and easygoing — he got along with everyone effortlessly and made us all feel welcome. One of the most memorable moments was when he pulled out his guitar and sang me “Happy Birthday.” It was such a thoughtful, personal touch that made the day feel even more magical. Throughout the entire experience, Mark paid incredible attention to detail, always checking in to make sure we were having a great time and had everything we needed. He was a great communicator leading up to the day, extremely accommodating to all of our requests, and even followed up after to make sure everything went smoothly. He also made safety a priority and got us back to shore safe and sound without a hitch. Captain Mark is not only a fantastic captain but a genuinely kind and thoughtful person. I couldn’t have asked for a better birthday or a better host. Highly, highly recommend!

Cruisers 420 Express Cruiser Rental in Long Island Sound

Captain Dirk and his boat made our Fourth of July one to remember! From the moment we stepped on board, Dirk was the picture of professionalism—warm, respectful, and incredibly knowledgeable. I’m 39 weeks pregnant and felt completely safe and cared for the entire time. The boat itself was pristine, spacious, and so comfortable—perfect for taking in the fireworks in style. Dirk went above and beyond to make sure everyone had a great time. Truly one of the best boating experiences I’ve ever had. Can’t recommend him enough!

Sunset, 3-6 Hour Cruises on Spacious Cruiser - Norwalk, Westport, Rowayton CT

Matt was Great! went out with my 8 year-old son, girlfriend and a friend for a three hour trip on the boat. Checked out the beautiful coastline and a couple of awesome swimming holes spent some time on the paddleboard.. such an awesome day. Can’t wait to take another trip out with Matt. Beautiful boat, very professional.!

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

Mark was super cool, and we had a great time overall. The only issue was that the zodiac boat at the front was blocking access to the bow, so we couldn’t use that part of the boat. We also wanted to swim, but there was probably a miscommunication — we ended up eating during the time we should’ve been swimming, and later Mark said it was too late. That was a bit disappointing, as we didn’t get to swim at all during our 4-hour trip. Everything felt safe and nice overall. Mark let us play any music we wanted, and everything was clean. A longer trip with more time would definitely be a better option next time.

Beautiful & Modern 35 Foot Express Cruiser!!

We had an amazing time with Captain Steve watching the sunset. The scenery was breathtaking, and the calmness of being out on the water made it truly unforgettable. Captain Steve was friendly, approachable, and kept the experience fun from start to finish. Highly recommend for a relaxing and memorable family outing!