Chatham Sailboat Rentals

Very happy with what we got with our sailing rental for two hours. Staff where super helpful and even offered a cheaper option that meant the two of us could sail together, we ended up having more fun.
I would not recommend for people who are more advanced as you are limited to the bay area where staff can see you. Otherwise great experience.
Also, don't know why but another reviewer is saying the sails are worn out, didn't notice that at all - on any of there boats.

My family and I spent a few days in Chatham this summer and this may have been the highlight of our entire trip. Everyday the kids wanted to go back, they couldn’t get enough. It looks like something out of a postcard. Beautiful beach and picturesque sand dunes. Very reasonably priced rentals. (Paddle boards and sailboats) Eric was extremely knowledgeable and took great care of us. They have a great shop and sandwich window that served burgers, hot dogs, and my personal favorite homemade lobster rolls!! AMAZING! We cannot wait to back next summer

We had a great experience with Chatham Sail. My two sons (10,15) and I spent the afternoon on a sailing lesson with Eric. This experience was a highlight for them of our trip to the Cape. Eric was very informative and taught them how to steer, use the wind and maneuver the boat. We saw seals which they thought was super cool! Eric was great with the kids and a super nice guy to be out on the water with! I recommend this for anyone who wants a little bit of adventure in their vacation!

We rented a hobie wave for 2 hours. Boat was old and the sail worn out. If you are not a sailing enthusiast and don't mind paying 120$ for a boat in this condition, go for it. There are better alternatives in the area...

Helpful folks, great location, terrific place to sail. Very accomodating!