2024 Sailing Season is coming! See you April 13, 2024!

Schooner Racing

Wednesday Night Racing in Annapolis on the Schooner WoodwindsWednesday Night Racing- Public Sails

Woodwind and Woodwind II will be match racing every Wednesday night when 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 Woodwind Captains…. Jen & Mickey.

See our Facebook Photos of our Wednesday Night Racing!

Great Chesapeake Bay Schooner Race on Schooner WoodwindGreat Chesapeake Bay Schooner Race

Every October, Woodwind races down the Chesapeake Bay from Annapolis, MD to Norfolk, VA.

Join our team in two different ways!

Race with us as “Guest” Crew: Learn 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.

Watch the Start of the Great Chesapeake Bay Schooner Race: Watch the very beginning of the race as it starts off of Annapolis. Join the fun as Woodwind II  sails as the spectator vessel for the Race. This sail departs the Annapolis City Marina to cheer on as many as 40 schooners as they set down the Bay for their 130 nautical mile journey to the mouth of the Bay. More info on the spectator boat will be posted to our Special Events Calendar.

Private Team Building Sailing Events on the Schooner WoodwindPrivate Team Building Cruises including Racing

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!

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