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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.
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.
Book with Longshore Sailing School
Verified experiences and guided adventures in the surrounding area.
Operated by Longshore Sailing School · Westport, Connecticut
Embark on an exhilarating private sailing experience with the RS Quest in Westport, Connecticut, offered by Longshore Sailing School. Ideal for experienced novices, this adventure invites you and up to three friends to navigate the peaceful waters aboard agile 14' RS Quest Sloop Dinghies. Feel the wind in your hair and the sun on your skin as you master essential sailing techniques and explore the coastline. The RS Quest's design makes it both stable and responsive, offering the perfect blend of challenge and safety. Whether you’re sharpening your sailing skills or simply soaking in the natural beauty, this trip offers memorable moments on the water. Don’t forget essentials like your photo ID, sunscreen, and a bathing suit to stay comfortable throughout your journey. With expert instructors ready to guide you, this private outing promises personalized attention and a chance to connect with the elements in a fun, supportive environment. Whether you're a local or visiting the coastal charm of Westport, this adventure makes for an unforgettable day on the water.
moderate.
2–3 hours.
Basic fitness is recommended as you will be actively handling the boat and moving around on deck.
No previous experience is required, but a basic understanding will enhance your comfort and enjoyment. Instructors provide guidance for novices.
Bring a photo ID, sunscreen, a bathing suit or quick-dry clothes, water, and a windbreaker depending on the weather.
The RS Quest is best for older teenagers and adults due to the physical demands of sailing and safety regulations.
You can bring up to three friends, making a total of four participants per private session.
Sessions may be rescheduled or canceled for safety reasons; the sailing school will notify you promptly with options.
Yes, all necessary sailing equipment including the boat, life jackets, and safety gear are included in your booking.
Westport’s coastal area has a rich maritime history, with sailing and fishing playing significant roles in its development throughout the 19th century.
Longshore Sailing School supports sustainable boating practices to minimize environmental impact on Long Island Sound and promote clean waterways.
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.
Book with Longshore Sailing School