My mom and dad and I went for a 2-hour morning sail. The location is easy to find with ample parking. When we arrived, our sailor and a member of the staff were on site and wearing t-shirts identifying themselves. It was a wonderful morning in every way. Josh, our sailor, was so pleasant, relaxed, informed, and kind. I cannot... More

I won't lie. I was a bit apprehensive when my daughter and her husband suggested that we go out for a sailing lesson. But Darius of Sail Montauk couldn't have been more welcoming and reassuring. We had to reschedule our cruise when some bad weather blew through, but Darius was most accommodating and was able to take us out the... More

I took the kids out and they had a blast. Our Captain, Luke Thomas, couldn't have been better with the kids. He taught them all aspects of sailing including names of the different parts of the boat, sailing language, knot tying and more. He made the trip enjoyable and the moment the kids got back on the dock they asked,... More

Booked a Taste of sailing trip, the process was so easy and the price I have to say is a steal for the service and experience! On the day we were to sail there was no wind, not even a breeze, so unfourtunetly Darius had to cancel the trip. After meeting Darius, we decided to cancel our plans for the... More

My husband and I were in Montauk celebrating his birthday with some much needed outdoor time. We chose this company based on the reviews and we are SO glad we did! Josh took us out, our bottle of wine in hand, for the 10 AM - Noon sailing. We were nursing a bit of a hangover and the cool air... More

I went to Montauk for the first time for my sister's bachelorette. There were nine girls and we chose the tandem sailing option through Sail Montauk. It was very relaxing and fun. Darius, the owner, responded faster than other companies which I appreciated. His co-captain, Josh was very chill. Darius had good energy and was enthusiastic. He taught the girls... More

I was looking for something special to do in Montauk with my teenage son Paul, and found it! Captain Darius was enthusiastic to share his love of sailing, and he gladly shared his knowledge and technical expertise with us! He was warm, friendly and let us share in a "hands-on" sailing experience! We even learned a few new knots! A... More

Four of us went out with Sail Montauk Sunday of Labor Day weekend and had the most amazing time. The boat was great and well stocked with water and sodas (which we barely touched as we brought a boat-load of rose) and Captain Darius was fantastic. We sailed through Lake Montauk and out into Block Island Sound. That portion was... More

I never sailed before even though I always wanted to. So I decided to take a two hour sailing lesson captain Darius who is an excellent instructor. It was a very exciting experience, pure fun !! I look forward to doing it again in the future.