Wind’s Up

This place is incredible. The perfect group of people running this place, most have been there for several seasons. I rented one of their 15 Ft sail boats here and took it out with my Girlfriend and we went right out and sailed the entire lagoon over the course of about 1.5 hours. The boat was in good shape and handled in the water well. The sail was in great shape too.
The prices are very affordable and it took literally no time to get out on the water, they rig for you and send you off.
The sailboats would fit 4 adults comfortably and the views in the lagoon are fantastic. Highly recommend this if you are in MV for any amount of time.
I noticed they have good kayaks and other adventure options as well. 5 stars, thanks Winds Up !

We sent the kids on a one hour kayak excursion. You can do half days and full days also. The attendant was very nice and helpful providing guidance to us and the kids. Rental prices were affordable and the location convenient. We also knew the kids would be safe and they all had a great first time. I’d strongly recommend it.

We had a great time on a windy afternoon in Vineyard Haven at Wind’s Up. It was my first time kayaking and they gave good and helpful instructions. Despite that, I had trouble in the wind so we came back after 15 minutes. So they put my husband and me in a double kayak which was great. Apparently, my slower more stable single just wasn’t designed to keep pace with his. I appreciated that they just charged us for the double. My large extended family who visits Vineyard Haven every summer said we’ll all be back now that we scouted it out for them! Thank you, Wind’s Up!

Wow, what can I say. Took my niece and nephews for lessons. The instructor was amazing and they had a wonderful time. Had to let them go on their own (one was timid in the water), so I was a bit hesitant and nervous (would their parents let them go alone?). This might have been the highlight of their vacation! Will go again on my own as the rentals are nice and you can either stay in the gentle waters of the lagoon or perhaps go out to the ocean (I am not good enough for that, but its an option for the more skilled kayakers). I have also rented for a week while staying at a waterfront property and they delivered the kayak; again, awesome service and convenience. You can not go wrong.

Wind’s Up is the island’s oldest business related to kayaks. You can rent or buy your kayak here and they will also deliver your rental to a different spot if you don’t want to explore the lagoon, the body of water they are located on. (I recommend either of the two great ponds which are purely magical to explore on a kayak.)
Please note that the map here on Unilocal indicates the wrong location. They are on the way out of town from the ferry as you go towards the hospital and the drawbridge that leads to Oak Bluffs.
This is a friendly, family oriented, seasonal shop that also sells bathing suits, wet suits, beach sandals, sun glasses, dry bags and waterproof cases, snorkeling gear and other items connected to water sports.
When I bought my own kayak, this is where I came. I knew I’d get a reasonable deal and the best advice.
Watch for their end of season sales when you can buy a great used kayak.