Rascal Sailing provides Instruction and Training, New Owner Support, and Yacht Relocation Services.

Instruction is based on the US Sailing Certification Series for Basic Keelboat and Basic Cruising. US Sailing sets the national standard for quality sailing instruction.

We are located on Five Mile River between Rowayton and Darien Connecticut. New owner support is available year round, relocation services and instruction are available from May through October.

Instructions and Training are provided on our C&C 99 a sleek 33 foot performance cruiser designed by Tim Jacket and built by Fairport Marine. Cruising World magazine awarded her "Best Performance Cruiser of the Year" and SAIL magazine has selected her as "one of the best boats of the year." She beat out the Beneteau First 36.7, the Farr 395 One–Design, a Dehler 36 and many others.

We are fully insured through the Chubb Insurance ‘Burgee Program’.*

Rascal Sailing President
Captain Wim Jessup

Explore the Islands, learn local history, and enjoy the sights and sounds of coves and marshes.

We offer Educational Cruises which sail out of Five Mile River on the 33 foot Sans Souci we can visit the Fish Islands, Ziegler’s Cove, pick up a mooring and have a bite to eat aboard, and head over to the Norwalk Islands. No sailing experience required and being ready to have fun and explore!


Join an experienced crew and learn different crew positions on a race boat team.

We race from early June through to early September.
Racing is on Sans Souci a C&C 99 with a performance handicap rating of 105.


Basic Cruising with Rascal Sailing

Learn the seamanship skills that will allow you to expand your horizons safely and enjoy time with family and friends while knowing what is necessary and important for your safety, comfort and enjoyment.


us sailing

Rascal-Sailing, LLC is a proud member of US Sailing Association and committed to the integrity and advancement of the sport of sailing in the United States.