Book RS Quest dinghies, catamarans, double and single kayaks, or 11'6" paddleboards in Westport, Connecticut.
RS Quest, 13' Wave Catamaran, 17' Getaway, double & single kayaks, and SUP.
water-activities · Westport
Set sail on the waters of Westport, Connecticut with the RS Quest—a perfect private sailing experience for small groups looking to enjoy the thrill of navigating the coast. Discover what makes this adventure both fun and safe for beginners and seasoned sailors alike.
Longshore Sailing School in Westport, Connecticut offers small-group watercraft experiences across a range of sailboats, kayaks, and paddleboards.
The fleet includes 14' RS Quest sloop dinghies, 13' Wave catamarans, 17' Getaway catamarans, sit-on-top single and double kayaks, and 11'6" BIC stand up paddleboards. Guests can book the RS Quest for up to three people; the 13' Wave catamaran accommodates up to four; the 17' Getaway catamaran accommodates up to five. Single kayaks and paddleboards suit solo paddlers, while double kayaks fit two people.
Each trip description notes basic essentials to bring such as a photo ID, sunscreen, and a bathing suit. The equipment mix supports novice through advanced skill levels: RS Quest boats and 13' Wave catamarans work well for experienced novices to intermediate sailors, while the 17' Getaway targets intermediate to advanced sailors. Sit-on-top kayaks and 11'6" paddleboards are ideal for recreational paddlers exploring Westport waters.
Longshore Sailing School focuses on safe, supervised outings on local waterways and provides clear trip information for each vessel. Reservations are arranged per trip type and group size, with each product summary stating capacity and suggested items to bring. For visitors seeking a range of small-boat options in Westport, Longshore Sailing School supplies a variety of well-specified watercraft experiences suitable for families, friends, and individual paddlers. Detailed product summaries help guests choose boats to match comfort, group size, and skill level, making planning straightforward for families, friends, and solo paddlers visiting Westport for on-water recreation and flexible booking options.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Coastal Connecticut destination
Sailing, kayaking, SUP options
Largest boat fits five people
Suggested items to bring
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Longshore Sailing School listing.
Longshore Sailing School offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Select the right vessel for group size and skill level, check the listed essentials, and reserve the RS Quest, catamaran, kayak, or paddleboard today.
boat-charters · Westport
Experience the thrill of sailing on a 13' Wave Catamaran in Westport, Connecticut. Perfect for beginners and intermediate sailors, this private adventure offers an unforgettable day on the water.
water-activities · Westport
Join Longshore Sailing School for a fun-filled Double Kayak adventure in Westport, Connecticut. Paddle together and enjoy stunning water views in this perfect outdoor experience for friends and family.
water-activities · Westport
Paddle at your own pace with Longshore Sailing School’s single kayak adventure in Westport, Connecticut. Enjoy peaceful waters, beautiful scenery, and a day of fun on the water!
water-activities · Westport
Glide through Westport's serene waters on an 11'6" paddleboard with Longshore Sailing School. Perfect for all skill levels, this adventure offers scenic views and a refreshing outdoor experience.
water-activities · Westport
Take to the waters of Long Island Sound on a 17' Getaway Catamaran in Westport, CT. Perfect for skilled sailors looking for speed and scenic sailing along the coast.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.