Watercraft Rentals & Sailing at Longshore Sailing School, Westport

Set on the shores of Long Island Sound in Westport, Connecticut, Longshore Sailing School offers an authentic gateway to water-based adventures for all ages and skill levels. This well-regarded facility is a cornerstone of the local recreation scene, providing a selection of well-maintained boats including 17' Getaway Catamarans, RS Quests, 13' Wave Catamarans, as well as single and double kayaks and stand-up paddleboards. Whether you’re stepping into your first sailing lesson or looking to rent a reliable craft for a day on the water, Longshore’s staff ensures a safe, approachable experience.

Westport’s location on the Sound presents consistent winds and calm bays, ideal for beginners but engaging enough for seasoned sailors. The sailing school’s structured programs emphasize water safety and sailing fundamentals, making it a trusted community hub for youth lessons and adult courses alike. The surrounding coastal environment provides a diverse backdrop — salt marshes, rocky shoreline, and open water that frequently hosts birds like osprey and heron.

Rentals are straightforward and affordable, with staff providing the necessary gear including life jackets. The school’s commitment to community shows through events like Sound cleanups and scholarship programs for local kids, highlighting a long-term dedication beyond just teaching sailing.

For visitors staying nearby, the proximity to vibrant downtown Westport means you can combine your on-water morning with excellent dining and local culture. Longshore Sailing School stands out because it makes the marine waters of Connecticut accessible, safe, and inviting, positioning Westport as a significant destination for coastal recreation on Long Island Sound.