Woodwind and Woodwind II will be match racing every Wednesday night that there is an Annapolis Yacht Club (AYC) Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers (“guest crew”) will be able to participate in helping to sail the boat and steer the boat, when appropriate of course. This will be America’s Cup style racing since it is match racing, so the competition will be very strong between the father and daughter teams who are the captains of each Woodwind.
Every October (this year, October 16-20), Woodwind races down the Chesapeake Bay from Annapolis, MD to Portsmouth, VA. Join our team! We train all “guest” crew how to sail Woodwind on our way from Annapolis to meet up with the other schooners in Baltimore’s Inner Harbor for a Parade of Sail with all the other participating schooners. The race starts just south of the Bay Bridge around 1:30 pm the next day. We break into crew watches and sail the boat day and night until we reach the finish line at Thimble Shoal Light at the mouth of the Chesapeake Bay. Racing 130 miles down the bay can take as little as 12 hours and as much as 40 hours depending on the wind speed and direction.
- Join our Team! Details and Pricing
- Past Schooner Races
- Facebook Photos of the Great Chesapeake Bay Schooner Race
Learning to sail is perfect for building successful teams. Sailing a 74-foot schooner requires teamwork, collaboration, trust, communication, and coordination—the core skills of high performance teams. Schooner Woodwind specializes in providing your group with the best and most unique teambuilding sailing experience in Annapolis or anywhere! Our professional captains and crew lead an exciting, hands-on sail training program on the Chesapeake aboard our 74-foot schooners Woodwind and Woodwind II. Choose from several teambuilding options, from the relaxing and informative “Team Fun” program to our flagship “Ultimate Team Challenge” program, which pits Woodwind vs. Woodwind II in an America’s Cup-style match race, with your group at the helm!