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 ! read more

Wind's Up - Sailing with GF @ Winds Up - Rafting/Kayaking Near Me - Vineyard Haven, Massachusetts

Jeff is the man. We rent kayaks every year from Winds Up. We got in a late today and Jeff helped us out getting everything we needed. And reserving online was super easy. read more

We had a GREAT day paddle boarding! Safety measures were in place and cleaning of all gear was visible. Reserving online was easy enough and I was grateful to be able to purchase a bathing suit in the shop. Thank you for making outdoor fun easy and relaxing:) read more

Wind's Up - Perfect activity for the whole family!!! - Rafting/Kayaking Near Me - Vineyard Haven, Massachusetts

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 Yelp 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. read more

Friendly and knowledgeable staff, good rental prices on paddle boards. We had to exchange one paddle board for a larger size because one of our party was taller, no problem. Their location on Lagoon Pond is the perfect spot to learn and explore. I would certainly rent from them again! read more

Went to Winds Up to rent surf boards and sign up for windsurfing lessons for our teenagers. As we arrived and said greeted the owner he was immediately gruff. We asked if they had beginner boards and he snapped at us. We asked if he had boards available and he said we had to look at his website. When asked if he could help us since we were standing right there in his shop, he told us he was not interested in helping us and "there were no more boards". The owner was unbelievably rude and all we wanted to do was give him our business. We have had a house on the island since 1985 and we have never experienced such rudeness. There are other places to go. Avoid this one, he thinks he has a monopoly but he doesn't. read more

Wow! Incredible staff and location! Extremely friendly and very accommodating. There's a huge list of equipment to rent- more than usual- and the prices are very very reasonable. Their deals (3 day, 7 day) are even better for what you're getting. The paddleboards deals are very reasonable, especially for Martha's Vineyard ! They even let us exchange a paddleboard when they were a bit too small and wobbly. Perfect location right in between Vineyard Haven harbor and the lagoon! Perfect for water sports. very laid back and wonderful Vineyard vibe. Can't wait to rent again next year ! read more

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. read more

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! read more

I've been to Winds Up three times, and the third time really was the charm. Kayaking at Winds Up is cheaper than at their competitor, Island Spirit Kayak, so that's what brought me to them, but what will keep me is the exemplary customer service I received on my third visit. I showed up with a friend a little before five, hoping to get in an hour before closing, which their website listed as six pm. Unfortunately those were their summer hours, and their winter hours are not as long. Regardless, when I explained the situation they let us borrow a kayak for twenty minutes for free. It was really nice of them, and I will be returning in the future. :) read more

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. read more

I had a really great experience with Wind's Up. They've been in business for a few decades and it shows; they're organized, informative, and helpful. Max helped me book a SUP lesson and I went out on the lagoon with Fred. Both guys were very friendly; my time there was fun and easy! read more