Longshore Sailing School in Westport, CT, offers top-notch sailing lessons and boat rentals on Long Island Sound. Perfect for beginners and seasoned paddlers alike, it’s a community-centered gateway to coastal adventure.
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Difficulty
easy
Duration
2–4 hours
Fitness Level
Moderate fitness recommended to handle paddling and sailing dynamics, but beginners welcome with instruction.
Wildlife
History
Longshore has a legacy as a community sailing hub with roots stretching back decades, emphasizing education and access for all ages.
Conservation
Longshore organizes regular cleanups and promotes eco-friendly boating practices to protect Long Island Sound’s fragile coastal ecosystem.
Longshore Sailing School
Longshore Sailing School in Westport, CT, offers top-notch sailing lessons and boat rentals on Long Island Sound. Perfect for beginners and seasoned paddlers alike, it’s a community-centered gateway to coastal adventure.
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.
Reserve your boat rental early
Weekends and summer days fill quickly, so book online in advance to secure your preferred craft.
Wear quick-drying clothing
Water temperatures can be cool, so clothes that dry fast will keep you comfortable during your outing.
Always wear a life jacket
Life jackets are mandatory and provided if you don’t have your own—wear them properly at all times on the water.
Check wind conditions
Winds vary daily; light breeze days are easier for beginners, while stronger winds offer a more thrilling sail.
Waterproof jacket
Keeps you dry during chilly spring breezes and occasional spray on the water.
spring
Sunscreen
Protects skin during prolonged exposure under open skies on the water.
summer
Water shoes
Provides grip and foot protection when launching and landing boats on rocky or sandy shores.
summer
Insulating layers
Essential for staying warm during cooler mornings and windier afternoons.
fall