2027 Registration is OPEN!

Junior Sailing School
Junior Adventure Programs
Adult Sailing School

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!

🌊 2027 SEASON PASSES. 2026 PRICES! 🛶 Why wait until summer to save? Our Kayak & Paddleboard Season Passes are available at EARLY BIRD PRICING! ☀️ Lock in 2026 rates for the entire 2027 season! 🛶 Paddle more. Spend less. 🌊 Enjoy unlimited su
🌊 2027 SEASON PASSES. 2026 PRICES! 🛶 Why wait until summer to save? Our Kayak & Paddleboard Season Passes are available at EARLY BIRD PRICING! ☀️ Lock in 2026 rates for the entire 2027 season! 🛶 Paddle more. Spend less. 🌊 Enjoy unlimited summer adventures on the water! *purchase via link in bio #westportct #kayak #fairfieldcounty #earlybird #longshoresailing
🍂 Leaves aren’t the only things falling… our prices are too! 🛶 Big savings on kayaks & sailboats 🛍️ 30% OFF apparel & accessories Limited inventory—once it’s gone, it’s gone! 🔗 Shop now! Link in bio.
🍂 Leaves aren’t the only things falling… our prices are too! 🛶 Big savings on kayaks & sailboats 🛍️ 30% OFF apparel & accessories Limited inventory—once it’s gone, it’s gone! 🔗 Shop now! Link in bio.
Better late than never. Turns out “sea legs” come in sets of four, too. 🐾⛵️ Happy belated National Dog Day from the sailing, kayaking and paddle boarding pups of Longshore! LSS Dog and cover model Cão was adopted from @daws_ct i
Better late than never. Turns out “sea legs” come in sets of four, too. 🐾⛵️ Happy belated National Dog Day from the sailing, kayaking and paddle boarding pups of Longshore! LSS Dog and cover model Cão was adopted from @daws_ct in January! She went from a rescue in Georgia to sailor with just a few private lessons at LSS!
2 weekends left!!! Don't miss out on your chance to get on the water this summer! Rentals available any time we are open. #westportct #summerfun
2 weekends left!!! Don't miss out on your chance to get on the water this summer! Rentals available any time we are open. #westportct #summerfun
Us too? #westportct #longshoresailingschool #sailing #fairfieldcounty
Be chic, come to Longshore! ⛵#sailing #weekend #chic
Be chic, come to Longshore! ⛵#sailing #weekend #chic
We couldn’t let the summer sail by without giving a huge shoutout to the incredible staff who make the magic happen every single day. Our staff of 40 are comprised of our office, instructors and beach. Each play a vital role in how we function
We couldn’t let the summer sail by without giving a huge shoutout to the incredible staff who make the magic happen every single day. Our staff of 40 are comprised of our office, instructors and beach. Each play a vital role in how we function. They’ve taught skills, cheered on victories, handled the chaos, made lifelong friendships, and somehow still show up smiling every morning. 😄 To the team that keeps us afloat (literally 😉), thank you for making this summer unforgettable. We wouldn’t—and definitely couldn’t—do it without you. #staffgoals #LongshoreSailingSchool #BestSummerEver #westportct
🌊 2027 SEASON PASSES. 2026 PRICES! 🛶 Why wait until summer to save? Our Kayak & Paddleboard Season Passes are available at EARLY BIRD PRICING! ☀️ Lock in 2026 rates for the entire 2027 season! 🛶 Paddle more. Spend less. 🌊 Enjoy unlimited su 🍂 Leaves aren’t the only things falling… our prices are too! 🛶 Big savings on kayaks & sailboats 🛍️ 30% OFF apparel & accessories Limited inventory—once it’s gone, it’s gone! 🔗 Shop now! Link in bio. Better late than never. Turns out “sea legs” come in sets of four, too. 🐾⛵️ Happy belated National Dog Day from the sailing, kayaking and paddle boarding pups of Longshore! LSS Dog and cover model Cão was adopted from @daws_ct i 2 weekends left!!! Don't miss out on your chance to get on the water this summer! Rentals available any time we are open. #westportct #summerfun
Us too? #westportct #longshoresailingschool #sailing #fairfieldcounty
Be chic, come to Longshore! ⛵#sailing #weekend #chic We couldn’t let the summer sail by without giving a huge shoutout to the incredible staff who make the magic happen every single day. Our staff of 40 are comprised of our office, instructors and beach. Each play a vital role in how we function
Person sailing in a small boat with "Longshore" on the sail.
Two people sailing an RS Quest boat with blue and white sails on a calm body of water, surrounded by greenery and buildings in the background.
Children in life jackets sailing small dinghies, smiling and enjoying the activity.
Two people sailing in a small sailboat with blue and white sails on a body of water.
Group of kids in life jackets smiling at the beach.
Two people sailing on a small boat with the branding "RS Quest". One person wears a red life jacket and the other gives a thumbs up.
Two children in life vests sailing a small blue sailboat labeled "Bug" on a lake, with "LONGSHORE" written on the sail. Other boats and a red buoy are in the background.
Sailboat on water with person wearing red life jacket and hat, yellow sail with "LONGSHORE" text, houses in background.
Boy sailing small dinghy on water wearing life jacket and sunglasses.
Two children sailing a small boat with "RS" logo and "Longshore Sailing School" text, wearing life jackets.
Small motorboat with a person onboard, labeled "Longshore Sailing School," on the water with shoreline in the background.
Two children kayaking on water, wearing blue life jackets and holding paddles.
Group of children and adults wearing life jackets carrying a small boat on a rocky beach by the water.
A person standing on a motorboat labeled 'Longshore Sailing School' on a body of water, with sailing school sailboats in the background.
Two people on a small motorboat in a calm river, wearing red life jackets, with green foliage and cloudy sky in the background.
Sailboats with colorful sails and "School Sailing Longshore" text on water, with American flag and buildings in background.
Aerial view of a lakeside area with a marina and small boats docked. Buildings and a pool are surrounded by trees, with a sandy shoreline and greenery. The water is dotted with parked sailboats and a few people are present near the dock.
Two people in a small sailboat and one person in a blue kayak.
Children and adults preparing a sailboat with 'LONGSHORE' written on the sail, standing on a rocky shore, with trees and a building in the background.
Group of people on small sailboats near a rocky shore with houses in the background.
Sailboat with blue and white sails on water, two people onboard wearing life vests and hats. Background with a shoreline, houses, trees, and two green sailboats with numbers.
A man steering a motorboat labeled 'LONGSHORE SAILING SCHOOL' in calm waters near a rocky shore.
A small motorboat labeled "Longshore Sailing School" on a body of water with two people onboard, near a shoreline with trees and buildings in the background.
Two children sailing in a small white sailboat labeled "Longshore," supervised by an adult in a red shirt and life jacket on the water.
Sailboats on a lake with people sailing, displaying sails marked 'Longshore', with a green forest background.
Four sailboats with colorful sails (red, yellow, green, blue) docked on a rocky shore, with people preparing for sailing on a calm body of water under a blue sky.
Four people on a sailboat with a red and black sail on a calm body of water, with a shoreline and houses in the background.
People on a dock preparing to sail small sailboats with green and white sails, on a body of water with houses in the background.
A collage featuring three images: a youth life jacket, a blue hoodie with a catamaran design, and two youths jumping in white logo t-shirts by the water.

GEAR UP! From apparel and accessories, to lifejackets and dry bags, the Longshore Store has it all.

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