The Best Sailboat Rentals Near Milford

Stylishly restored classic 1970 Columbia 36 Yacht Private Sailing Tours

We had an amazing experience with Ian! The boat was beautiful and the route we took was too! Ian made sure we were comfortable the whole time, and took good care of us. We couldn’t have asked for any more, it was perfect. Thank you!!

Sailing NYC with Brooklyn Sail

Great experience to see the city! Ian is awesome and knows the city well. Besides the pictures and views, sailing towards the Statue of Liberty was a moving experience. Would definitely recommend to anyone in the area. Thanks Ian!

The Only 40ft Hinckley Sailboat in NYC Harbor – Sail in Style!

We had an AMAZING experience! The boat was clean, comfortable, and offered fantastic views. We appreciated the smooth ride and the opportunity to take stunning photos of the Statue of Liberty up close. Highly recommend!!!

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

Extraordinary experience on a comfortable and beautiful catamaran, with an excellent itinerary from Sag Harbor to Shelter Island for lunch and back. Captain Brian was super professional as was first Mate Erin in implementing and serving our extensive wines and hors d’oeuvres. The vibe of the team was fun, efficient but still chill. I highly recommend this as one of my best summer experiences and I’ve been in here my whole life and I’m in the hospitality business as a boutique hotel owner.

A Fully Crewed Luxurious Schooner Perfect for Sails and Events 12 - 41 Guests

We had such a fabulous time on this beautiful boat. Our captain, JM, and the crew Liz and Andrew were so friendly and attentive and amazing with all the kids we had. It was a wonderful afternoon and we can’t wait to do it again!

The Only 40ft Hinckley Sailboat in NYC Harbor – Sail in Style!

Wow! What a magical way to celebrate my birthday!! From the moment I inquired about booking with Captain Andy, he greeted me with such warmth and enthusiasm. On the day of, he was so welcoming towards my family and I, handling us with such patience and care, ensuring our safety and comfort. And, let’s not forget the level of skill he harnessed as we sailed the Hudson! We took on a few waves; there was a particularly big one that quickly became the highlight of our trip. Some members of my family have had bad experiences in water, but I was delighted to share and witness their excitement around facing it. Trusting in Captain Andy’s years of sailing experience we were all free to embrace a little splash. My little sister’s reaction was especially precious, as it was her first time being aboard a boat. “More waves! More!” Haha! Thank You, Captain Andy for such a memorable sail experience. This definitely won’t be my last time booking. To those of you reading, what are you waiting for?! Book him!!