Latest Past Events

Mother’s Day Brunch aboard the Schooner Woodwind

Annapolis Sailing Cruises Schooner Woodwind 80 Compromise St., Annapolis

Our Mother’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and […]

Wednesday Night Sailboat Races

Annapolis Yacht Club 2 Compromise St, Annapolis

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 […]

August Wine in the Wind

Annapolis Sailing Cruises Schooner Woodwind 80 Compromise St., Annapolis

Join us for a two-hour sail around the Chesapeake Bay while sampling wonderful wines from Portugal.  The representative from the winery will introduce you to four special wines while we are under sail. The […]