Dear Captain Bob Such happy memories of the most relaxing & enjoyable sail on your beautiful boat . You made us so welcome with your warm engaging humor , and we knew we were in good capable hands ! We look forward to our third sail with you this coming season . There's no other Captain for us ! WE LOVE YOU CAPTAIN BOB Thank you again Captain Bob for yet another adventure On your lovely boat . My family & I enjoyed a sunset sail that will be a treasured memory . My nephew was put to good use helping with the sails loving every minute You have fun entertaining stories along the way creating such an easy comfortable atmosphere . No one compares with your sails . See you next year You da man Captain Bob read more

Great sailing up to the north fork and back on the 34' Catalina. She's no spring chicken but this boat is in great shape and sails well with a very comfortable sail plan and cockpit layout. Felt balanced with minimal tuning and she gets up and going pretty quick through tacks with those 34' feet without everyone on board wondering if their driver (me!) is crazy. Reaching at 6.5 kts with a very comfortable, stylish lean. Even gave my 5 year old a little time at the helm in 17 kts winds on the way back. No weather helm, no problem. Will be back next summer! read more

Went for my 2-day asa Keelboat certification and had a wonderful experience. My Instructor Mark was a great teacher. He was very knowledgeable and patient with all his Trainees. Our second day was a rainy, cool, and mostly windless however Mark still made our sailing time worthwhile. Wish we spent more time out to sea and less in class however the class time did prove to be valuable. Will certainly return to continue my asa certifications. Thank you to Bob as well who runs a very good and wonderfully situated sail school in Sag Harbor. read more

My son and I wanted an accredited sailing course so we took the ASA Beginner Course [2 days] and had a great experience sailing around Sag Harbor and Shelter Island. Mark is both an experienced and wise teacher who truly loves the profession and a seasoned sailor who made the course both enjoyable and stress free: this is a great combination. We will certainly return for the next level certification and to charter sail boats in the near future. An added surprise was a BBQ that Bob prepared when we finished to course on the last day. read more

My wife and I recently completed the American Sailing Association's Basic Keelboat Sailing Course with Mark at Sag Harbor Sailing. Even though I've been sailing of and on for decades, I learned a tremendous amount, as did my wife, who's not very experienced. Mark is a great teacher and really put maximum effort into communicating his knowledge to us. I've also chartered the 23-foot Ensigns from the company. The boats are in excellent shape and the staff at SHS is most accommodating and pleasant to deal with. read more

Went for a 2 hour lesson with our 10 year old Grandson, and had a fantastic time. Paul was very knowledgeable and fun to talk with throughout the lesson. Even though the wind was light and variable, we were still able to practice most of the basic sailing maneuvers. After spending a week with us on the North Fork that included horse back riding, a trip to the Hampton beaches, art classes, and lots of great food, he told his parents that his favorite time was the sailing lesson at Sag Harbor. read more

I've been renting sailboats around the NY area for years and this was by far the best experience we've had overall! The boat is in excellent condition and fully equipped. Bob was incredibly helpful. He gave us a full run down on the systems and tons of tips on where to sail. The sailing area is outstandingly good and the conditions were perfect. Couldn't have for anything better for a day out sailing with the family. Can't wait to go back! read more

We had a great sunset sail on the 23' Pearson with Paul as Captain. As mediocre sailors, he was the perfect balance between a hands on Captain and terrific company! Many laughs were had, despite getting soaked from choppy conditions! The boat was comfortable for 4 (large) adults. We hope to sail again with Sag Harbor Sailing, as the rental process was seamless. Will recommend to friends and clients who are visiting the East End! read more

My wife and I took the ASA 101 course over a weekend in early fall. Mark was our instructor. We had the best time and learned a huge amount in two days. Sailing in Noyak Bay was protected enough not to be scary but we had good wind and really got a sense of the power even a 23 foot boat develops. Probably the best think I've ever done and in a casual and welcoming environment. Highlight recommend it. read more

Thoroughly enjoyed the sailing lesson with Sag Harbor Sailing and would highly recommend others who have an interest in sailing. I signed up for 2 hr lesson + guest. Instructor was knowledgeable, friendly and gave equal instruction to both my wife and I. I have an interest in sailing so this was very beneficial. However if you never sailed before but would like to try you will enjoy as well. read more

Chartered a sailboat on Monday (6/7) to take some family members sailing. I rented the 23′ Pearson Ensign which had plenty of room for the five of us and Capt. Paul. We had a great afternoon sailing and Capt. Paul was great! Highly recommend Sag Harbor Sailing, the Pearson is a very sable boat and fun the sail. The roller reef jib setup made for easy use of the jib. A fun day for all. read more

Great fun sailing with these guys a second time. First time was with a captain and this time we rented on our own after we got comfortable with the bay. Mark, one of the owners was very helpful with tips about the boat and the area and he made sure we had a great experience. The boat was clean, well maintained, set up for us on arrival and it was safe. Highly recommend. read more

We have rented sailboats both with and without a captain and Sag Harbor Sailing was terrific in both situations. It was a good experience and there's really nothing better than seeing the area from the water! Our guests were thrilled to be out on the water and we had no doubts about how the equipment would hold up. It made for amazing days. Will definitely do it again! read more

We had an absolutely fantastic time out on the water. Mark helped us get all set up on the boat and showed us where we were on our chart. The boat worked like a dream and we had some great wind. The staff were helpful and the experience itself was excellent. Even had great communication leading up to the day itself to help with booking and logistics. Thank you!! read more

Great experience. Father and son on this 4-hour charter. Captain Bob was excellent. He was very friendly and cordial and made it a very pleasant morning -- he knew the spots, provided all the bait and instructions we needed and helped make it a successful morning. PS - we got lots of porgies and a large fluke, all of which he cleaned for us. A great day. read more

My wife and I sailed with Captain Mark the day after our wedding and had a terrific time. We took out the 23 footer which was very reasonably priced for a private tour with a captain. We enjoyed a relaxing cruise with champagne and snacks Mark was very knowledgeable about the area and provided a sailing tutorial for us. I would highly recommend this company. read more

Capt Bob is the best - the knowledge that we received was awesome! Capt Bob is a highly skillful instructor and you feel extremely safe when you are out on the water with him. In the classroom, he is right on the money! And lets not forget Steve - he is awesome too! I Definitely ( highly ) recommend Sag Harbor Sailing, Inc - the only way to learn! read more

My wife and I had a great time during our sailing lesson. Mark is a great instructor, explained everything, answered all our questions and did not put any pressure on us as newbies when we messed up. The boat was in great shape, well taken care of. This is definitely the place to go if you want to try sailing. We're definitely coming back. read more

I've only done my certification there , but as far as ASA 101 goes ... in class and on the water I was really happy with it. Very kind stuff, very understanding and informative. No question was left unanswered. If you want to really learn sailing as a beginner, and pass ASA cert with it , this is the place to take it. read more