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South Shore PaddleBoards

4.5 (11 reviews)

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Photo of Claire T.
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5 years ago

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11 years ago

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7 years ago

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5 years ago

Karen is awesome, she has always taken great care of me and special orders show up quickly

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10 years ago

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7 years ago

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Connetquot River Kayaking and Paddleboards - Kayak

Connetquot River Kayaking and Paddleboards

3.9(7 reviews)
8.8 mi

5 stars, I highly recommend kayaking the Connetquot River with Connetquot River Kayaking. It's…read moreone of the best kayaking experiences I've had. Went kayaking with some friends today and we all had a wonderful time. The service and equipment was great, the guide was enthusiastic, friendly and informative, the scenery was spectacular and we saw incredible wildlife.

Lisa E. and I were recently gifted with a used tandem 14.5 foot tandem kayak. Lisa is cautious,…read morewhere as I am hellbent. Seeking to ease her into a passion for paddling , I sought out a group experience on calm waters. Safe was the operative word. I saw a social media posting for a guided tour of the Connetquot charging a small fee for dropping in your own vessel. They run this tour weekend days. Until November. There was a group of about 17, some with their own kayaks or SUPs, others rented from the business. Rob provided great direction, was informative , and a genial host. Lisa and I probably had time during the 2 hours to have small conversations with everyone in the group. The canals and river were so easy to navigate, scenic, tranquil, even with some light powerboat traffic. Not an abundance of wildlife but we had a great close encounter with a great blue heron. We are probably comfortable doing this without guidance now, but might choose to join up again for the group experience! Check it out while the weather is fine and the waters are warm! P.S. - I fell out of the boat before we even launched. Looked the fool in front of all but that just started the day off with laughter.

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Connetquot River Kayaking and Paddleboards - Kayak

Kayak

Connetquot River Kayaking and Paddleboards
Connetquot River Kayaking and Paddleboards - Kayaking on the scenic river

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JK KAYAK & SUP - Cold Spring Harbor SUP

JK KAYAK & SUP

4.9(51 reviews)
14.0 mi

What a great experience we had with JK Kayak and SUP. This was our first time kayaking and we…read morewere in great hands with Joe and Connor. The website provided all the information we needed to be prepared for our adventure. Upon arrival, Joe and Connor got us fitted with our safety vests and our kayaks and then gave us lessons on how to use the paddle, get in/out of the kayak and provided general navigation and waterway guidance; from there we were off and loving life! We kayaked in Cold Spring Harbor just behind the lab and had an awesome time. It was so relaxing and quiet as we glided across the water. Joe led us in the front and Connor picked up the rear so we always felt safe and in good hands. Since this was our first time, we opted for a 1hour lesson/tour and Joe told us that most of his customers, at the end of the tour, say they wanted more time. We all felt the same way and can't wait to go back. If you're thinking about kayaking... go for it and definitely do it with JK Kayak & SUP. You won't be disappointed. Thanks Joe and Connor for such a fun afternoon!!!

My 13-year old nephew and I had a great time on our 2-hour tour with Joe. My nephew was I…read morefirst-time kayaker, and Joe patiently taught him the ins and outs of getting around. Joe was also very knowledgeable about the geography, wildlife, and history of the area. Our next trip is already booked!

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JK KAYAK & SUP - Southampton

Southampton

JK KAYAK & SUP - Refreshing dip off SUP board in Cold Spring Harbor

Refreshing dip off SUP board in Cold Spring Harbor

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Stony Brook Harbor Kayak & Paddleboard Rentals

Stony Brook Harbor Kayak & Paddleboard Rentals

4.9(11 reviews)
17.7 mi

What an amazing first experience! For years I've been wanting to try this place out and we finally…read moredid. We rented paddle boards for a great fee. They gave great information upon booking the reservation on the phone. Parking was very easy but depending what time you go I'd go sooner for parking! The women who checked us in was very sweet. She explained everything to us. She told us where to go and how to stay safe. The man who got us on the boards was equally as nice. He gave us a quick course on how to use the boards. The boards were much easy than I thought. I felt secure and got the hang of it pretty quickly. We paddled to an amazing area with a waterfall and past some beautiful houses and shoreline. I loved that you could kneel , lay , stand and just float in the water. It was definitely a fun day and I can't wait to do it again.

This has become a summer tradition; have been both kayaking and SUP. Went out on the water again…read moretoday and truly enjoyed taking in the beautiful scenery and just being out on the water on a blistering hot day. They've got an informative video if you're unfamiliar with the area and they're always happy to give you pointers. Sign up is easy. Equipment is clean and in good condition. The other folks out on the water are always so nice as well helping one another out with pictures...it's a great clientele. Do yourself a favor and go out and enjoy all that is summertime!

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Stony Brook Harbor Kayak & Paddleboard Rentals
Stony Brook Harbor Kayak & Paddleboard Rentals
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Sailing Montauk's Catamaran Mon Tiki - Our best group photo in MTK - maybe ever

Sailing Montauk's Catamaran Mon Tiki

4.7(70 reviews)
76.8 mi

This was a highlight of our bougie Bachelorette party in Montauk! We rented our own private…read morecatamaran for six people for three hours. It was about $700+ after fees, tip, etc, and it was totally worth it. Our captain, Mason, was super cool. He was friendly, knowledgeable, and we felt comfortable being really annoying and weird in front of him. The sail itself was just a short ride in the bay, where we anchored close to a beach. We loved dancing on the boat, trying out the SUP board (included), basically chugging our BYOB drinks (no hard liquor allowed on board), taking pics lounging in the net, gawking at the yachts, and pretending the pool noodles were seahorses that we were riding. Bachelorette stuff! I think we had the Mon Mini boat, probably the smallest option. Included: one SUP board, bluetooth speaker, cooler, two pool noodles, the captain.

I booked the 26' catamaran for a Friday sunset cruise from 5-7pm. The catamaran was larger than I…read moreexpected. Also, the bean bag chairs were very comfortable compared to other boats. They provided two Yeti coolers and a Bluetooth speaker for music which was nice. The staff were very friendly and helpful. They helped take pictures for our group and the sailing was very smooth. I would definitely book again, probably earlier in the summer for the 3 hour cruise to be able to do the paddleboarding.

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Sailing Montauk's Catamaran Mon Tiki - Little guy loved it

Little guy loved it

Sailing Montauk's Catamaran Mon Tiki - 26' catamaran boat

26' catamaran boat

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South Shore PaddleBoards - paddleboarding - Updated May 2026

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