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October Sailing Schedule

Sailing on the Schooner WoodwindOctober is a wonderful time of year to sail.

  • Typical breezy conditions
  • Cooler temps
  • Fall Foliage turns mid-October
  • Many super, special event cruises
Please note that our sailing schedule varies from our normal schedule due to the Boat Shows.  We are displaced from our normal dock at the Annapolis Waterfront Hotel so our cruises depart elsewhere. All info is included in the details link.

October 1-3: No Public Cruises. Private Cruises can be booked and are encouraged.

October 4-8: 1.5 Hour Public Cruises departing up to four times daily from inside of the Sailboat Show. Get your Combo Tickets where we package the cruise and Boat Show Admission together! This deal discounts the Boat Show Admission ticket by up to 40% when bought online when you pick a time to sail. SAIL BOAT SHOW CRUISE INFO & TICKETS

October 7, Sunday: Specialty Cruise: “Brews in the Breeze Lunch Cruise” Sail on a lunchtime cruise of craft beer tasting on the Chesapeake Bay. After we raise all our sails, we will start the tasting with the lightest of the four beers. Cruise departs from Annapolis City Marina.  SOLD OUT

October 10-16: Special Cruises below offered and Private Cruises can be booked and are encouraged.

October 11, Thursday: Specialty Cruise: “Schooner Race Watch”Cheer on the Schooners! The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. Cruise departs from Annapolis City Marina.  SOLD OUT

October 14, Sunday: Specialty Cruise: “Lighthouse Cruise”Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. Cruise departs from Annapolis City Marina.  SOLD OUT

October 17, Wednesday: Public, 2-hour, Sailing Cruises resume at the Annapolis Waterfront Hotel. More Info…

October 28: Last Day of Public Cruises More Info…  Private Cruises can be arranged through October.

October 31: Last Day of Private Cruises, more info Private Cruises

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