Summer 2026 is HERE!!

Spaces still available for youth and adult classes!

We are OPEN 4th of July Weekend for Rentals and Private Sails!

Click below to rent, or call us to book a private sail!

Book Your Rental Online!
Gift Cards
Junior Program Information
Adult Program Information

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.

SAFETY, FUN, LEARNING

Red, white, blue, and sailing too. Wishing everyone a happy and safe Fourth of July from Longshore Sailing School! #longshoresailingschool #westportct #sailing #fairfieldcounty #july4th
Red, white, blue, and sailing too. Wishing everyone a happy and safe Fourth of July from Longshore Sailing School! #longshoresailingschool #westportct #sailing #fairfieldcounty #july4th
Smiles, sunshine, and sailing! ☀️⛵ Our incredible Sailing instructors are making Week 2 of Junior Programs one to remember. Whether you’re stepping onto a boat for the first time or building on your skills, there’s a place for you on the
Smiles, sunshine, and sailing! ☀️⛵ Our incredible Sailing instructors are making Week 2 of Junior Programs one to remember. Whether you’re stepping onto a boat for the first time or building on your skills, there’s a place for you on the water. Come sail with us this summer! 🌊 #westportct #longshoresailingschool #fairfieldcountyct #sailing #longislandsound
Rigged and ready. Beat the heat and head on down to the waterfront. #WestportCT #sailing #longshoresailingschool #fairfieldcounty #longshoresailing
We have plenty of availability for private lessons and joyrides for July 4th Weekend!! These will fill up, so call us at (203) 226-4646 to book! Celebrate America’s 250th on the water in Westport! #sailing #westport #july4th
We have plenty of availability for private lessons and joyrides for July 4th Weekend!! These will fill up, so call us at (203) 226-4646 to book! Celebrate America’s 250th on the water in Westport! #sailing #westport #july4th
The storm packed up. The clouds stayed for the after-party. Days like this remind us how special this place is. 🤩💙☁️🌥️☀️⚓️ #LongshoreSailingSchool #westportct #fairfieldcounty #saugatuck #storm
The storm packed up. The clouds stayed for the after-party. Days like this remind us how special this place is. 🤩💙☁️🌥️☀️⚓️ #LongshoreSailingSchool #westportct #fairfieldcounty #saugatuck #storm
Not exactly a picture perfect summer day. We had chilly air, cool water, and some afternoon rain but you’d never know it from the smiles on the docks. Our sailors and paddlers kicked off the first day of Junior Program with great attitudes, lo
Not exactly a picture perfect summer day. We had chilly air, cool water, and some afternoon rain but you’d never know it from the smiles on the docks. Our sailors and paddlers kicked off the first day of Junior Program with great attitudes, lots of energy, and a willingness to embrace whatever the weather brought. Here's to sunny days ahead! 🤩🥳🫶🏼⛵️🛶🚤⛱️
We have private lessons available ALL DAY on Sunday! ☀️⛵️Perfect for a family outing or brushing up on some sailing skills! Call us to book. #westportct #longshoresailingschool #fairfieldcounty #summer
Red, white, blue, and sailing too. Wishing everyone a happy and safe Fourth of July from Longshore Sailing School! #longshoresailingschool #westportct #sailing #fairfieldcounty #july4th Smiles, sunshine, and sailing! ☀️⛵ Our incredible Sailing instructors are making Week 2 of Junior Programs one to remember. Whether you’re stepping onto a boat for the first time or building on your skills, there’s a place for you on the
Rigged and ready. Beat the heat and head on down to the waterfront. #WestportCT #sailing #longshoresailingschool #fairfieldcounty #longshoresailing
We have plenty of availability for private lessons and joyrides for July 4th Weekend!! These will fill up, so call us at (203) 226-4646 to book! Celebrate America’s 250th on the water in Westport! #sailing #westport #july4th The storm packed up. The clouds stayed for the after-party. Days like this remind us how special this place is. 🤩💙☁️🌥️☀️⚓️ #LongshoreSailingSchool #westportct #fairfieldcounty #saugatuck #storm Not exactly a picture perfect summer day. We had chilly air, cool water, and some afternoon rain but you’d never know it from the smiles on the docks. Our sailors and paddlers kicked off the first day of Junior Program with great attitudes, lo
We have private lessons available ALL DAY on Sunday! ☀️⛵️Perfect for a family outing or brushing up on some sailing skills! Call us to book. #westportct #longshoresailingschool #fairfieldcounty #summer

Click a photo below to follow us on Instagram!

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.

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