Reviews for Small Group Sailing and Swim Charter in Sag Harbor, Hamptons

My friends and i had the best time on Luna with Sail Hamptons!!! We had the best crew and it was the most fun day of our two week trip. truly could not have asked for anything more. we already can't wait for next year.

Starlight is a beautiful and well appointed sailing yacht! Everything you could ever want in a sailing adventure - world class! And the Captain is incredibly gracious and knowledgeable! A true mariner and sailor! The doggie crew is just adorable to boot! Will not disappoint! Do it!

Captain Leland took 6 of us for a dinner cruise and tour of Sag Harbor and Shelter Island aboard Soleil. We had a surprisingly smooth voyage considering the amount of wind and chop in the water. Very experienced captain with top notch hospitality and local knowledge. 10/10 experience, would definitely do this again!

I’ve done many charters in Montauk and this is by far the best! Thank you so much to Captain Toby, his wonderful team, and their beautiful boat for a perfect day!!!

I had the pleasure of sailing onboard Starlight with Captain Toby as crew chef. In my 12 years of crewing as chef I have to say I’ve worked with all kinds of captains and Toby is just simply the best there is. He’s laid back and knowledgeable , and makes his guests and crew feel completely at home right away. Take the trip, go sailing !!! You won’t regret it.

We had a fantastic charter on Starlight out of Sag Harbor - seamless and easy booking, fun crew and a perfect half day! Everyone in our group from a 3 year old toddler on up had a blast, including swimming, paddle boarding etc. We would definitely book again.

We had the best experience on Luna. Kayla, Dylan, and Toby were so helpful and attentive. Highly recommend if you’re looking for a relaxing and fun day at sea!

Had a wonderful time with Toby and his crew (including puppy Grace!) for a friend’s bachelorette. They were all so kind and attentive and accommodating, and our group had a fabulous time. Highly recommend!

I can’t say enough positive things about my experience with Captain Toby! From our initial booking and leading up to our charter he was so helpful and responsive to all of our groups questions and requests. He provided a bunch of recommendations for lunch options for on board and we had a delicious lunch that was delivered seamlessly to the boat. His crew did an amazing job setting everything up and serving our group of 12. They were fun, friendly and attentive. It truly was a wonderful experience few didn’t want to end. Looking forward to my next charter with Captain Toby & Sail Hamptons in the future!

My friends and I had the BEST time on the Luna sail yacht with Captain Toby and his amazing crew. They couldn’t be friendlier, were so fun and attentive. They gave us recommendations for lunch to bring a board and they set everything up on their beautiful dishware. Once we got on the boat, we didn’t have to worry about a thing. Worth every penny. Can’t wait for our next excursion. Thank you Sail Hamptons!!!!

Our son had his Bar ”Boat” Mitzvah on this incredible sailboat this past August 2020. Toby and crew were great from start to finish, everyone aboard had a great experience and something to remember on that special day. Thank you again, JL 5 STARS to you.

Highly recommend. Capt Toby and his team on the Cosmos created a terrific team building experience for my work colleagues and I. They Can’t wait to return for a personal experience!

Capt. Toby and his team are total professionals and run a first rate operation. If you haven't experienced the Hamptons from the water you are missing out. I've sailed with Capt Toby out east a few times and have had an amazing experience!

The crew was great. Catering to my needs at all times Once boarding the crew had everything setup for us so nicely. And the whole day flowed so well. Thank you Dylan and the crew (Breanna, MJ, Katlin and others.

Amazing boat with experienced crew 👍👍👍 …

I booked Luna with my friends for my birthday and it was simply amazing. Relaxing and tons of fun. Captain Kayla, MJ and bri were so sweet and just a pleasure the whole time. All the guests were so pleased with everything.

Jesse & Rebecca were amazing- we had a wonderful celebration sailing & floating & paddle boarding!

Spent Saturday afternoon on the Luna with 17 girls for a bachelorette party this weekend. The staff aboard was excellent - shout out to Captain Toby! We had the best time and they really took care of us. We didn't have to lift a finger! They served us cocktails and put out platters of food. All we had to do was supply it. 10/10 would do this again!

Reliable and so nice! Had the best time. Highly recommend!

I had a charter with Sail Hamptons on Saturday for my bachelorette weekend, and I genuinely cannot say enough amazing things about the experience. From start to finish, it was absolutely incredible and exceeded every expectation we had. Jessie was phenomenal. He was so kind, personable, and patient, and he took the time to explain the mechanics of the sailboat and what he was doing throughout the trip. Rebecca was also absolutely amazing. She was incredibly attentive, diligent, helpful, and kind throughout the entire charter. She went above and beyond to make sure we had everything we needed and honestly felt like one of the girls by the end of the day! And then there was Scout, the sweetest cat on board! 🐱 We absolutely loved him. Jessie let us pass Scout around, which was such a fun and completely spontaneous part of the day that we will never forget. Even if the weather had been terrible, I genuinely feel like the staff and the overall experience would have made it worth it!

If you are thinking about booking with Captain Toby and his crew, DO IT. We were on Luna for my Bachelorette with 17 girls - Captain Toby, Liz and Connor were so attentive, but equally let us do our thing and have fun. We would definitely do it all over again if we could!

This boat trip, owner and crew is one of the best companies around and one of the best days I have ever spent in Sag Harbor hands down. Highly recommended ⛵️🏆 …

I have been a guest aboard Starlight both in Sag Harbor area and in the Virgin Islands. She's a luxurious, seaworthy yacht and Capt Toby is a knowledgeable mariner and a great host, who knows all the best spots to visit. Boat dog Bamboo is very sweet and a very relaxing presence on the boat. It's fun to lie on deck and meditate with her in the sun.

Incredible experience with Captain Toby aboard the Luna. We were celebrating a birthday and the whole crew took care of everything from beverages to catering to cake! Would love to sail with them again!

I had the immense pleasure of sailing on Starlight with Toby for 5 days from Bermuda to Newport. It was a life changing experience in so many ways. For someone who wants to learn about sailing, Toby is a wealth of knowledge and experience, with the right amount of patience. If you want to just sit back in comfort and sip a cocktail, Starlight is top luxury. The vessel has every comfort you could want, but personal and individualized (unlike larger group charters or cruises). I highly recommend spending time on Starlight!!!

We had the best time with captain Toby and crew aboard Luna! The staff were so attentive and made our experience so special. They even helped resolve a payment misunderstanding which was extremely generous of them, and really speaks to their commitment to their clientele. Would recommend them for any charter in the Hamptons.

We love our chatters with Sail Hamptons! We have been several times and have also recommended them to friends that have had a great experience. Highly recommend them!

Had a wonderful time with Toby and his crew (including puppy Grace!) for a friend’s bachelorette. They were all so kind and attentive and accommodating, and our group had a fabulous time. Highly recommend!

I can’t say enough positive things about my experience with Captain Toby! From our initial booking and leading up to our charter he was so helpful and responsive to all of our groups questions and requests. He provided a bunch of recommendations for lunch options for on board and we had a delicious lunch that was delivered seamlessly to the boat. His crew did an amazing job setting everything up and serving our group of 12. They were fun, friendly and attentive. It truly was a wonderful experience few didn’t want to end. Looking forward to my next charter with Captain Toby & Sail Hamptons in the future!

We really enjoyed our time with Sail Hamptons! We rented the Cosmos boat for a birthday celebration and had lots of fun. The service was amazing and we were able to take out paddle boards and get into the water and swim. Will definitely be back next summer.