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Chatham, MA

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Chatham Sailboat Rentals

4.5 (6 reviews)
Closed • 10:00 am - 6:00 pm

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7 years ago

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1 year ago

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5 years ago

Absolutely amazing experience. Everyone was lovely and the boats were so much fun. We went back for a second time

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6 years ago

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Fun Seekers

Fun Seekers

5.0(10 reviews)
17.8 mi

Being rather un-athletic I was nervous about trying my hand at Stand Up Paddleboard (SUP) but was…read moreconvinced by friends that I could do it. We met our guide, Erik, at 8:30 am on a beautiful August day at a crystal-clear pond in Welfleet where I was immediately put at at ease by our guide's calm demeanor. We began with a history lesson of SUP-ing followed by precise, but easy to understand instructions that we practiced on the shore. Then we were off to learn in the still waters of the pond. Despite my initial reluctance I found SUP-ing to be rather easy, aided, of course, by Erik's natural teaching ability. He was able to keep an eye on all 8 in our group and provide differentiated instruction, based on each of our individual skill level. He never made me feel like I was holding the others in the group back but rather, he advanced my skill and confidence while simultaneously improving the technique of the more advanced in our group. We were all able to enjoy our nearly hour long paddle around the perimeter of the pond, at our owns comfort and speed, before our lesson was complete and Erik headed off to do a wind-surfing tour. Hmmm...Maybe I'll try THAT next? ;-) The tour was easy to arrange, at a time convenient for us and was very reasonably priced. We were provided with good quality, modern equipment that was well maintained. It is easy to see why Fun-Seekers comes so highly recommended because Erik is an established professional who truly loves what he does! We plan to book another lesson soon and would not hesitate to suggest Fun-Seekers to others!

Cool laid back little sailing spot. Rented a Wing. It was awesome. Great time in the OBXread more

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Fun Seekers - First day Surfing!

First day Surfing!

Fun Seekers
Fun Seekers

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Chatham Kayak Company

Chatham Kayak Company

4.7(9 reviews)
0.9 mi

Overall very positive experience. We reserved two tandem kayaks online. When we showed up, they…read morewere expecting us. The young man working was very friendly - got our paperwork done and into our kayaks very quickly. Very helpful when we asked for advice on where to head, since we weren't very familiar with the waterway. We totally enjoyed our 1 1/2 hours on the water. The staff were there to greet us and help us out when we returned. An unexpected but really nice development was they reached out a few days later to let me know I might have double booked, and was charged for four kayaks instead of two. I emailed back to say that I had only booked two, and they promptly let me know they would credit back the two extra ones. Impressed me!

A colorful sea shack with the equally colorful proprietor, John. So much fun to rent kayaks and…read morepaddle boards from here. John really knows his stuff however and makes sure everyone is safely aboard. Prices are very reasonable and there's a wide selection of both kayaks and boards. We even got to use the custom built beautifully crafted wooden kayak, which slipped through the water effortlessly with elegance and grace. John is a good soul who looks after his clients and also is a known to rescue ferrets! See photos!

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Chatham Kayak Company - Looking onto the river from the dock

Looking onto the river from the dock

Chatham Kayak Company
Chatham Kayak Company - Hat's, Beach Towels, and assorted sized T-Shirts for sale all with Chatham Kayak Logo embroidered. Get yours today.

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Hat's, Beach Towels, and assorted sized T-Shirts for sale all with Chatham Kayak Logo embroidered. Get yours today.

Chatham Sailboat Rentals - sailing - Updated November 2026

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