This place is incredible. The perfect group of people running this place, most have been there for…read moreseveral 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 !

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

Wonderful time kayaking on Sengekontacket Pond. Booking and release forms all easily done online…read more Plenty of parking and staff got us right on the water with quick and simple instructions. Highly recommended.

Easy booking, no early arrival necessary- just show up, check in and go. Friendly staff, solid…read moreequipment. Laid back, no cheesy tour script. Me and my son had a really nice kayak tour w/Trevor.

This is one of the only places on island that you can rent sailboats, kayaks and paddle boards…read more They are so accessible to the community and are reasonably priced. They also do sailing lessons and all their instructors are incredibly knowledgeable and kind. I've been so impressed with their staff at not only this rental site but also in the camps that my kids are enrolled in. All around great organization that adds so much fun to our vacation on Nantucket.

From the owner: Rentals NCS' Jetties Sailing Center offers rentals of SUP…read morepaddle boards, kayaks (single & double), and windsurfers. The Jetties Sailing Center also offers sailboat rentals in a variety of sizes and models. Private Lessons The Jetties Sailing Center also offers private sailing lessons in Rhodes 19s, Marshall Cat 15s, Sunfish, windsurfers, Lasers, the Hobie Getaway (and 420s per the Program Director). Lessons can be booked from 10am-12pm, 1-3pm, and 3-5pm. Lessons are available 7 days/week and may be scheduled by calling the Jetties Sailing Center (508-228-5358), by speaking with an employee at the customer service shack, or by booking online in the summer months.

We recently took a paddleboarding lesson and mini tour of a local lake in Brewster. This was our…read morefirst time paddleboarding. Our instructor, Shea, was on point! He made it a blast for the 3 kids of varying ages as well As for the adults. It was peaceful and relaxing, but also fun and we learned a lot! I hope to return next month for a sunset or glow SUP adventure! In addition the owner Ryan, was incredibly responsive to my questions and got us in quickly! This place did not disappoint.. I only wish we could have stayed out there a day:) Highly recommend!

What a wonderful time we had!!! It was a beautiful night. The glowing SUP was awesome and all the…read morewildlife we saw on the trip. Tiffany was an excellent guide and had us newbies up and going in no time. We would definitely do this tour again! THANK YOU!

Standing on water is totally awesome. Standing on water is the most natural thing in the world and…read morea stand up paddle board affords that delight very easily. I rented 2 stand up paddle boards for the day with my friends. We started at the flat water of the pond on the other side of state beach. There are some great natural areas and a paddle board is an amazing way to tool around on the ocean. The people that run Waz Sup, Aaron and Lori are super cool. They gave a quick lesson and even though I was the only person who had SUPed before, everybody got the hang of it in a couple minutes. This is kind of new business venture for them and were really working hard to ensure we had a good time. This is definitely the rental outfit I would choose for renting board. They took my card at the beach and emailed a receipt. There were willing to off any help we needed and were friendly and cool about the whole thing. It does not take long to get good enough on flat water to try waves out. We took the boards and headed out to Ables hill and got them bitches on the ocean. It is a far different and more challenging experience being on surf. I was able to get up a few times but Mike Hall was rocking out, even standing on his head few times. They deliver the boards wherever you are, so even though they are at state beach sometimes you just tell them where you would like to go, or get a recommendation of what beach is best and they drop off and pick up the boards. It's really a great value and amazing exercise.

Paddle Boarding really took our Martha's Vineyard vacation to the next level. I started a few days…read moreago as a total newbie and even road a few waves in just yesterday. We rented for the entire day on State Beach, and even loaded the paddle boards up in our Jeep and took them to another beach on the Vineyard. All we had to do was give WazSUP a ring at the end of the day and they swung by and picked them up from us. We had so much fun paddle boarding we thought about buying a couple and realized we're better off letting WazSUP take care of all that for us instead. You really can't beat their delivery and pickup service. Great price, helpful instructors, a super fun and convenient business they're running.

Rideaway Adventures - Mashpee, Cape Cod Boomsauce Score: BS +++ (Amazing location! now that's…read moreboomsauce!) Tried booking through TripAdvisor--bit funky. So I went straight to the source and connected with Mike Morrison, who was not only professional and honest, but genuinely invested in making our family kayak dream happen. He even dropped a discount code like a true Cape Cod MVP. The experience? Unreal. We paddled out to a private beach only accessible by boat--and it was to die for. Calm waters, untouched shoreline, and the kind of peace that makes you forget your inbox exists. I still can't believe people get to do this regularly. It was truly memorable, and Rideaway made it seamless. They also offer sunset tours and paddle board rentals, which we're already eyeing for next time. The staff? Mostly young, but super informative, professional, and full of good vibes. Rideaway doesn't just rent gear--they curate moments. Boomsauce Scale B- basura (trash) BS basic (come on! Try harder) BS + better (Yo! That's better) BS ++ best (alright! Alright! Alrightttt!) BS +++ Amazing location! now that's boomsauce!

Lovely afternoon getaway during Fall. It was a nice and tranquil experience kayaking through a…read moresmall river and seeing some beaches. I rented a kayak for two people for 6 hour and paid $75 before tax. I made the reservation online and the process was pretty seamless. A staff mentioned that they were fully booked throughout August and September but we were there innOctober which was off-peak so it was really quiet.

Great instruction, well-kept equipment, have done both surf and stand up paddle and very satisfied…read morewith the experience. Great access to beautiful parts of the island otherwise inaccessible, and not crowded. Highly recommended!

From the owner: We offer Stand Up Paddle Lessons and Tours far from the crowded vineyard shores. Our equipment and…read moreour experience is second to none. Even well seasoned Stand Up Paddle Boarders find elements of SUP that that they have never experienced before!

I've driven by this shop forever and when I needed a new rash guard stopped in... Rachel, the woman…read moreworking that day, was super helpful and friendly. I was surprised at how much is packed in this place. Everything you'd expect in a surf shop--surfboards, stand-up paddle boards, skimboards, kayaks, bodyboards, skateboards, swimwear, beach stuff, watches, and a lot more... When most of the other surf shops haven't opened for the season yet, this saved me a drive farther up Cape

Good selection, and still somehow quite a bit of options considering the inside is TINY. Service is…read morealways super friendly, and the prices are the same as all across the cape. Unless of course you go to tj max lol.

Eric was so kind to take us out on a last min addition to his day. He was fun to talk with about…read moreChatham, sailing and the tides. Definitely rent a sailboat or take a lesson from him/business.

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