CAPTAIN WIM JESSUP

An experienced Cruiser + Racer having completed multiple races to Bermuda, Halifax and the Vineyard.

My passion is to cruise with my family and friends on Long Island Sound and explore the many gems it has to offer. I also enjoy racing on the Sound with a good boat and a good team! I appreciate what we have right here in our backyard with its varied harbors, coves and beautiful anchorages. We don’t have to go far to experience the magic.

  • U.S. Coast Guard Licensed Mariner- OUPV
  • U.S Sailing Certified Basic Keelboat Instructor
  • Director of the Marine Training Center at Landfall Navigation
  • Assistant Head Sailing Instructor at Sound Sailing Center in Norwalk, CT
  • Commissioner on the Five Mile River Commission
  • Former Manager of the Milford Yacht Club, GM of the Indian Harbor YC , GM of the Larchmont YC
  • Former Chairman of Save The Sound
  • Treasurer of the Indian Harbor Sailing Foundation which supports youth sailing

Sailing is a lifelong adventure. I love to teach and want to share that adventure with others which is why I have commissioned Rascal Sailing LLC.