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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
moderate
Duration
2–3 hours
Fitness Level
Basic fitness is recommended as you will be actively handling the boat and moving around on deck.
Wildlife
History
Westport’s coastal area has a rich maritime history, with sailing and fishing playing significant roles in its development throughout the 19th century.
Conservation
Longshore Sailing School supports sustainable boating practices to minimize environmental impact on Long Island Sound and promote clean waterways.
Longshore Sailing School
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.
Location
Westport, CT
Coastal Connecticut destination
Tours Offered
6 Trips
Sailing, kayaking, SUP options
Max Capacity
Up to 5
Largest boat fits five people
Essentials
Photo ID & sunscreen
Suggested items to bring
Select the right vessel for group size and skill level, check the listed essentials, and reserve the RS Quest, catamaran, kayak, or paddleboard today.
Wear Sunscreen
Protect skin from prolonged sun exposure while sailing, even on cloudy days.
Bring a Photo ID
A valid photo ID is required for check-in and safety verification.
Dress for Water Activities
Wear a bathing suit or quick-dry clothing to stay comfortable in case of splashes.
Stay Hydrated
Bring water or sports drinks to maintain hydration during the trip.
Sunscreen
Protects skin from UV rays during prolonged sun exposure on the water.
summer
Water Bottle
Keeps you hydrated during your sailing adventure.
Quick-Dry Clothing
Ensures comfort if you get splashed or wet while sailing.
spring
Windbreaker Jacket
Provides warmth and protection against chilly winds on the water.
fall