Sail the Chesapeake on one of two, 74-foot wooden, schooners that offer a real Chesapeake Bay sailing experience for 2-hour public cruises, as well as longer specialty cruises. Sail past the US Naval Academy, gorgeous homes, and the historic city skyline. Raise the sails, steer the boat, or simply sit back and relax with a cold beverage. During the weeknights, we have History Mondays, Beer Tasting Tuesdays, Wednesday Night Match Racing, and Thursday Local Music Cruises. We have a cash bar filled with local craft beer and wine. Certified for 48 passengers on each schooner. Departs from the downtown Annapolis Waterfront Hotel.