Summer program registration is OPEN!

Register NOW!

See you for our 2025 opening on May 24!

SAFETY, FUN, LEARNING

Longshore Sailing School is a community boating and rental facility located at the mouth of the Saugatuck River on the Long Island Sound. In addition to our junior and adult learn to sail programs, we offer sailboat, kayak, and paddle-board rentals, provide private lessons, and host private events.

LSS is open to the public - No membership required, no need to own or lease your own vessel to participate in our courses.

Click a photo below to follow us on Instagram!

We are hiring! Hear from Owen directly about his time at LSS! Application in links.
Hear from Brandon on why you should apply to work with us! Full video, employment details and application may be found on our website! Linked in bio.
Did you know that we have our own weather station? Whether you're checking the wind to see if you'll get blown away walking the dog this winter or planning a summer sail, check out the most hyperlocal info available! Linktree linked!
Did you know that we have our own weather station? Whether you're checking the wind to see if you'll get blown away walking the dog this winter or planning a summer sail, check out the most hyperlocal info available! Linktree linked!
🍂 Autumn Clearout: Enjoy 50% Off Everything! 🍁 (*excluding kayaks*) Stock up on your favorites before they’re gone! Discount applied in cart- Linktree in Bio
🍂 Autumn Clearout: Enjoy 50% Off Everything! 🍁 (*excluding kayaks*) Stock up on your favorites before they’re gone! Discount applied in cart- Linktree in Bio
Once you're one of us, we're family forever. Here's to you Mr. Andrew Morrison-Baratz! Of course known to LSS forever and always as "Baratz". We wish for smooth sailing for you and Amy! @admorrison57 #longshoresailingschool #mustymustard
Once you're one of us, we're family forever. Here's to you Mr. Andrew Morrison-Baratz! Of course known to LSS forever and always as "Baratz". We wish for smooth sailing for you and Amy! @admorrison57 #longshoresailingschool #mustymustard #castaways #onemoreyear
All operators and passengers in paddlecraft are required to wear properly fitting life jackets in good repair from October 1st through May 31st in Connecticut. Reminders: Always wear your Life Jacket! -File a Float Plan: Boaters should always let so
All operators and passengers in paddlecraft are required to wear properly fitting life jackets in good repair from October 1st through May 31st in Connecticut. Reminders: Always wear your Life Jacket! -File a Float Plan: Boaters should always let someone know where they are going and when they expect to return. -Dress for Cold Water: The correct clothes can keep you comfortable, extend your season, and save your life. -Safety Gear and Equipment: Make sure your safety gear and communication equipment are maintained, charged and working properly. Both Connecticut and federal law require a sound producing device onboard all vessels. -Maintain a Proper Lookout -Following Proper Maintenance Procedures
Big thanks to this crew for getting our docks safely and quickly out of the water today! No pressure like a rising tide chasing the clock! It was the fastest we've ever pulled them! #westportct #longshoresailingschool #docks #fairfieldcounty #sailing
Big thanks to this crew for getting our docks safely and quickly out of the water today! No pressure like a rising tide chasing the clock! It was the fastest we've ever pulled them! #westportct #longshoresailingschool #docks #fairfieldcounty #sailing #autumn #bestshipsarefriendships
Show up and support! Join us October 9th, 7:30pm at the Westport Town Hall Auditorium. Showing up shows your support for LSS and supports LSS keeping its' home! #longshoresailingschool #longshoresailing #sailing #westportct #fairfieldcounty #203
We are reigniting our efforts to support @clubenavalpovoacao! Let's share our passion for sailing! Jane will be traveling back to Povoaçao, Açores in November to bring repair materials, parts and maintenance expertise to support their e
We are reigniting our efforts to support @clubenavalpovoacao! Let's share our passion for sailing! Jane will be traveling back to Povoaçao, Açores in November to bring repair materials, parts and maintenance expertise to support their efforts in junior sailing. Please consider a donation to our fundraiser. ANY amount helps. While on site, we provide maintenance training, program development, coaching and more. Please note, all of Jane's travel expenses are personally funded. ALL donations go directly to the intended program/purchasing supplies. Link in bio for our GoFundMe. #sailing #supportyouthsailing #azores #açores #optis #ilca #community #povoação
Jane was honored to be featured in WindCheck Magazine's September issue of "On Watch". Interested in her career, national awards and what brought her to LSS? Click the link in our bio! #longshoresailingschool #windcheck #sailing #westportct
Jane was honored to be featured in WindCheck Magazine's September issue of "On Watch". Interested in her career, national awards and what brought her to LSS? Click the link in our bio! #longshoresailingschool #windcheck #sailing #westportct #sailingschool #ussailing
We are hiring! Hear from Owen directly about his time at LSS! Application in links.
Hear from Brandon on why you should apply to work with us! Full video, employment details and application may be found on our website! Linked in bio.
Did you know that we have our own weather station? Whether you're checking the wind to see if you'll get blown away walking the dog this winter or planning a summer sail, check out the most hyperlocal info available! Linktree linked! 🍂 Autumn Clearout: Enjoy 50% Off Everything! 🍁 (*excluding kayaks*) Stock up on your favorites before they’re gone! Discount applied in cart- Linktree in Bio Once you're one of us, we're family forever. Here's to you Mr. Andrew Morrison-Baratz! Of course known to LSS forever and always as "Baratz". We wish for smooth sailing for you and Amy! @admorrison57 #longshoresailingschool #mustymustard All operators and passengers in paddlecraft are required to wear properly fitting life jackets in good repair from October 1st through May 31st in Connecticut. Reminders: Always wear your Life Jacket! -File a Float Plan: Boaters should always let so Big thanks to this crew for getting our docks safely and quickly out of the water today! No pressure like a rising tide chasing the clock! It was the fastest we've ever pulled them! #westportct #longshoresailingschool #docks #fairfieldcounty #sailing
Show up and support! Join us October 9th, 7:30pm at the Westport Town Hall Auditorium. Showing up shows your support for LSS and supports LSS keeping its' home! #longshoresailingschool #longshoresailing #sailing #westportct #fairfieldcounty #203
We are reigniting our efforts to support @clubenavalpovoacao! Let's share our passion for sailing! Jane will be traveling back to Povoaçao, Açores in November to bring repair materials, parts and maintenance expertise to support their e Jane was honored to be featured in WindCheck Magazine's September issue of "On Watch". Interested in her career, national awards and what brought her to LSS? Click the link in our bio! #longshoresailingschool #windcheck #sailing #westportct
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GEAR UP! From apparel and accessories, to lifejackets and dry bags, the Longshore Store has it all.

Items are available for in-store pickup and shipping!