Plymouth Yacht Club

Plymouth Yacht Club sits right on Cape Cod Bay at 34 Union Street, putting you in one of New England's most storied sailing waters with easy access to Plymouth Harbor. The club runs a full junior sailing program for kids ages 7–17, so it's a great pick if you're bringing the family along. The staff are genuinely friendly and helpful, and overnight stays run $75 per night with boat-side service available on weekends.