Fantastic place to rent kayaks, sail boats, SUPs, or to take lessons. Very highly recommend-- it's always fun. The equipment is in excellent condition, new and clean. In addition to rentals they also offer classes for age 8-adult. The classes are very popular so they fill quickly. Although they don't rent powerboats, they now also offer US Powerboating classes, so you can get that training and certification. My son took it, and it's a really good class. Westport is beautiful from the water, and we enjoy renting there several times a summer. The office staff is very knowledgable and make both renting and signing-up for an appropriate class very easy. The beach crew that launches you also offers very helpful tips based on the wind and tide. There is substantial area to paddle in that is not impacted by tide. However, if you insist on paddling up Gray's Creek be sure to look at the tide chart BEFORE, or you could get stuck. I have rented there many times, and the staff has always told me when to avoid the tidal areas. So be sure to follow their advice, or it's on you. Since they have a lookout watching-out for the renters at all times, they will rescue you though, mud and all. read more

Fantastic classes, private instruction and also rentals for both my kids and me. My family rents kayaks and sailboats there and the staff is always friendly and helpful. They recommend where to boat based on the tide and wind, and send people in a powerboat to help you if you get stuck or capsize. They're always keeping an eye on the renters and the weather and the prices are unbeatable read more

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Longshore Sailing School is the best! Our children have attended for many years - the school grows with kids and their needs and interests. The instructors are always caring, attentive and knowledgable. read more

quality equipment, friendly and knowledgeable staff. fair price. have rented many times and will do so again for kayaks and sailing

WOW!!! we had a little family reunion in Westport last weekend and our sailing trip with Ava and Lilly was the absolute highlight! Both of these young ladies took us on such a fun trip around the sound! There were 7 of us on two boats. and the folks in the office/gift shop were super friendly as well. Just not enough words to express how fun it was!! Gorgeous weather, fun conversation and great experience. We cannot WAIT to return!!! read more

I have been a huge fan of LSS for more than 25 years! Their educational programs are top notch! They bring the fun and the emphasis on safety. Their on-line rental reservation. program is a new and welcome feature. read more

Longshore Sailing School - The Fellas! - Sailing Near Me - Westport, Connecticut

A great way to learn to sail or just rent a sailboat for fun (with it without a skipper to help you) or just play about on a paddleboard. Located on the mouth of the Saugatuck river with its old local gentle breeze. Lots of fun and fair prices. read more

A professional, bright, safety conscious bunch....OMG...These guys are the absolute BEST!

fantastic rentals amazing and easy service. read more

Longshore Sailing School - Sailing Near Me - Westport, Connecticut

This place is a hidden gem! We moved to Westport four years ago and discovered it. Since then we've done the adult learn to sail class, our daughter took classes and along the way we've rented kayaks and SUPs. If we have company come for a visit we take them to Longshore because we know they would be impressed and have fun! It has become a summer routine that we all love. read more

I have had only WONDERFUL experiences at Longshore Sailing School. The staff is well-trained, friendly and informative. Every kayak I've rented is always in great shape. The location is beautiful and if you love being on the water, you are in for a treat. The boundaries within which LSS requires you to stay are not at all restrictive and the staff makes sure you know what they are. I have taken out rentals at LSS dozens of times, and the experience never feels repetitive. Tides, breezes, time of day, and general weather conditions and their interplay make each experience unique and memorable. (It is only good sense to think responsibly and to make yourself aware of those conditions when you are heading out.) It is clear from what I have observed over time is that the kids in the sailing school are having a great time and there is plenty of staff working with each group. LSS is a popular destination so reserve in advance by phone or email, especially on weekends. Enjoy!!! read more

Super convenient and a great choice of well-maintained rental sailboats.

I seldom write a review but felt I must because it was such an excellent experience! I went to Longshore Sailing School with my children, grandchildren, and even great grandchildren! I was so nervous but the staff and the owner Jane, in particular, were so reassuring and supportive. With their help I was able to get in the kayak safely and oh, how wonderful! All the while we were out there a staff member would come and check-in on us. We were welcomed back at the shore when we were done. Chatting with a staff member afterwards, he told me that he had been watching me from the lookout and was happy I had such a good time. This is all great, but really it's better than that because I'm 90 years young....! I encourage all to head over there, it's awesome. read more

Longshore Sailing is a true gem in Westport! Office staff was welcoming and hospitable and helped answer all questions I had. The Hobie Getaway was an amazing time, and our trip to Cockenoe was blissful, yet exciting! Can't wait to go back again. read more

We rented SUP boards for an hour and had a fun experience until we got stranded. After paddling out for 30 minute, we tried to turn around to return our boards. To our surprise, the winds and currents were extremely strong. After 20 minutes of hard paddling, we weren't making progress. A nice man on a boat saw our struggle and offered us a ride to safely. Upon our return, a rescue boat from the company shouted over to us "all good girls, what happened?" We informed him of the situation and he seemed happy we were ok. When we got to shore, we were scolded by the company saying that we signed a waiver in which we wouldn't get in any other boats other than the Longshore boats. There was no "glad you're ok"... and the Longshore employees were extremely rude to our savior. We had no choice in the situation as their recuse boats were no where to be found and we didn't have phones to contact them. We were never warned of the harsh conditions, given a suggested safe route, or even informed about the safety boats. Lately, they tried to overcharge us ... we obviously didn't pay :) read more

We're visiting from Seattle and were delighted to find this sailing school. Great set up. Easy place to park, rent a boat and launch. The boats were in good condition - clean, good working order, responsive. The front staff and crew on the deck were helpful. Life vests were in good working condition for the kids and adults. Clean and usable. Sign up online was very easy to do with times, check out and waivers. Wonderful experience overall! read more

This is an amazing resource for those looking to get out into the waters of Long Island Sound. The location just simply cannot be beat as it's right at the head of the Saugatuck River, the waters are protected, and calm. For families they've sit on top kayaks you can go up the river in or brave out into calm waters. Small boats, lessons, and a great vibe via staff. This is surely the best resource around for boating and lessons. read more

Longshore Sailing School - Rental Fleet - Sailing Near Me - Westport, Connecticut

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If you are going to rent a SUP or Kayak go to DOWN UNDER near the the Westport Train St. .. STAY AWAY FROM LONGSHORE!!! The new management and particular staff are rude,condescending, smug, and provoking...Jane the owner needs to speak with the Mitchell's or Leonard's on how to work appropriately with customers. The attitude and obnoxious way has really soured my perspective on my view of the sailing school. I am a 45+ year resident of Westport and three-time graduate of the sailing school when I was a kid. They want photo ID to rent, which is acceptable except for the fact it's posted on a postcard at the desk. I was ready to offer them my cell phone and car keys, but they were emphatic About policy, something I never dealt with before when renting because I knew so many people there. Any PS Jane the owner made a point after the fact not to reconcile the problem but exacerbate it and in front of my daughter. The best part this was on Father's Day. read more

This sailing school and boat rental is a gem in Westport. Our kids have gone through the sailing program and they are well trained not only on safe sailing but also proper boat care and etiquette. My husband and I did a couples weekend course which got us up to speed on the basics of sailing. After going through the sailing school, we are all quite capable of sailing and we often rent the boats there. My kids loved it and LSS is a part of their fond childhood memories. My eldest loved being on the water and sailing so much she joined the staff in the summers. The staff is young but pleasant and professional. There is a fun vibe and on a beautiful summer day in CT, there's no better place to be. LSS is a small and locally owned business. It can be hard to please everyone but in my experiences at LSS over the last 17 years, I've never experienced any problems with them. The owner is hands on and truly cares about her boaters, her business and her staff. Even through the challenges of the pandemic and weather challenges, she has handled the changing guidelines and safety protocols gracefully. LSS is one of the many gifts that Westport has to offer read more

Such a fun afternoon! My gal-pals and I went to Longshore to kayak last weekend. My gals are basically pros at kayaking (LOL) but it was my first time and the Longshore staff was so helpful. I can't stress how helpful and knowledgeable that staff was and they even offered to take our pix and posted on their Instagram! Can't wait for the next girl's trip to kayak again and will DEF be going to Longshore for all of my kayaking needs!!! #kayak #girlstrip read more

Incredibly helpful instructors! We always have the best time kayaking and pattleboarding or sailing a hobie getaway with an instructor. Longshore is one of the amazing amenities Westport has to offer! I highly recommend heading to Longshore this summer! read more

LOVE LOVE LOVE!!! The most amazing genuine staff and perfect location to go out on the water! Definitely recommend great equipment and school! read more

We rent catamarans from Longshore a few times a summer. It's great fun and we're thrilled they have this available in the area. All their staff is always so pleasant and helpful! read more

STAY AWAY FROM LONGSHORE! IS RIGHT!! The staff nor the owner Jane were helpful or customer focused at all. My daughter is 12 years old and it was her first time on a paddle board. I was willing to pay $75 an hour for a one hour instruction and they told me that it would not be necessary. I was a bit surprised at the response. Needless to say she didn't have a good experience at all! At no point was there anyone helping her or monitoring the activity with the paddle boards, kayaks or sailboats. There were no safety protocols in place. I spoke to Jane and explained to her what had transpired and she said that if we didn't like our experience to go elsewhere. A very disappointing and troubling experience. The attitude and arrogance was quite shocking! read more

I rented an rs quest with my 3 kids (10, 9 & 9 yrs old) who had never been on a sailboat before. I used to sail a lot in my teens and 20's. Lucky those skills haven't been forgotten. When we arrived, the office staff welcomed us and had my reservation on file. We were directed to get life jackets and head down to the dock. Our boat was ready for us, we hopped in and went on our way after being told the boundaries. We had so much fun. The kids got a chance to experience sailing, steer the boat, ask me a million questions about sailing. Got stuck on the bottom a few times, but that's what I get for renting a boat close to low tide :) Upon our return to the dock, a class was getting ready to go out, yet the staff stepped away and guided me in to where he wanted me to land. So proud of myself that I didn't crash, but made a jibe and landed on a dime. I signed my kids up for sailing lessons in July. They are so excited! Thanks LSS for a great afternoon sail!! read more

I was visiting relatives in town this past weekend and they suggested we head to Longshore. Collectively there were seven of us. So we had a double kayak, paddle board and a Hobie wave. The fresh air was awesome! The whole staff was wearing masks and the life jackets were washed between each renter. It was so awesome to be out on the water with great friends. Thanks, Longshore! read more

Be forewarned. When you get out there on the Sound, you're on your own. They will tell you they watch out for you, but that is not the case. We had a party of four, including two ten-year-olds that had no paddleboard experience. We got hit with a swift current and strong winds and ended up on the other side of the bay, stuck against a rock wall. We waved our paddles for help for 45 minutes but got no response. They insisted they were watching, but that doesn't add up, considering they didn't launch the rescue boat for another hour. Then, when questioned about it, the manager told us, "if you didn't enjoy your experience, then don't come back." They acknowledged later the conditions were rough, but didn't mention that when we left. Also, one of our wives called when we didn't come back on time, and warned them that it was unusual for us not to return after our one hour time. Warning was seemingly ignored. read more

I just signed my children up for classes next summer and I love the season pass option! Our whole family got excited thinking about our great summer ahead. We love the atmosphere and the friendly staff While having fun is key, safety is their number one priority, and as parents we really appreciate that. read more

Had a great time here today renting a couple Hobie Getaways with friends. We received good phone instructions about parking and tides from them while booking the reservation, which I appreciated. The river mouth makes for some nice sailing and there are good landmarks like rocks and islands to which you can sail. read more

What a beautiful spot for an afternoon paddle. I called ahead of time, made to make a reservation and the young lady on the phone was so helpful in reminding me that I needed shoes I didn't mind getting wet and a photo ID, she even reccomended the best time for me to come in regards to the tides. When we got there the beach staff were welcoming and friendly and advised us on the best areas to paddle to based on the weather conditions. They have a lookout at all times so you never have to worry about getting stuck. The management and general staff were all delightful and the best part is you can bring your dog! It was a little chilly when we got off the water so I bought a sweatshirt that was reasonably priced and so cozy it is my favorite sweatshirt to this day. The office girls were very knowledgeable about the classes being offered and gave great recommendations as to which classes would be best suitable for us. If you live outside of Westport you have to park in a lot kind of far away but who cares on a beautiful day! I will definitely be revisiting the sailing school and will hopefully be participating in the adult beginner sailing class. read more

Really good place overall, nice people with white shirts, they had great service towards me while I was renting the canoe.

Paddle surfed here for the first time. Had a great time during a lovely Sunday afternoon. Fun time to spend with family or friends!

This is one of the best - perhaps the best - community sailing outfits in the country. It's a great resource for Westport, but is also open to the public. The instructors are professional and knowledgeable, and they love what they do and it shows. read more