We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers: Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Step off the dock and onto one of our private sailboats for an exhilarating sail on the waters of Montauk. Take the tiller or just sit back and relax; we'll make your sailing experience one of a kind. Get a Taste of Sailing with our private 2 hour...more
Hours Today: 08:00 - 20:00
See all hours
Suggested duration: 2-3 hours
32 Star Island Rd, Slip 412, Montauk, NY 11954-5271
All reviews amazing experience actual experience great teacher great conversation trip enjoyable bring your own alcohol beautiful sunset awesome captain fun experience bachelorette party two hours ali lesson ally boats instructor flotilla
What a great way to celebrate the end of summer. If you are looking for a party boat this is not it. It is a small, sweet sailboat with a great captain (Brian!) who plays good music, has great conversation and shares his love of...More
One of the Best Things I Did in the Hamptons this Summer! After a 5-day sailing course at Montauk Sailing, I earned my basic sailing certification. Ally (and her husband, Darius) are both such genuine, nice people and patient instructors. And how can you beat...More
My girlfriend and I had a fun and very enjoyable sunset cruise. You can bring your own alcohol and food. Plus the captain let's you control the boat and teach you about sailing if you like. Very friendly, made me and my girlfriend want to...More
Myself and 7 other friends rented 2 sailboats for a flotilla party and it was one of the best things we’ve done all summer! Darius and Lauren were great captains and really facilitated an amazing experience. While booking, I spoke with Allie who was very...More
We do not have a catamaran but for a group your size I would suggest one of our Flotilla Boat Parties. Book multiple boats and sail along side each other flotilla style. Raft up for picnic parties and swimming... More
We do not have a catamaran but for a group your size I would suggest one of our Flotilla Boat Parties. Book multiple boats and sail along side each other flotilla style. Raft up for picnic parties and swimming, experience a head to head race or play cat and mouse with waterguns to gain bragging rights for the season. All of our sails are hands on, so do as much or as little as you want. Perfect for bachelor/bachelorette parties, corporate events, family reunions and team building workshops.
I hope this answers your question!