October Sailing Schedule

Sailing in October on the Schooner Woodwind

October 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 Marriott Waterfront Hotel so our cruises depart elsewhere.

Sail during the US Sailboat Show

October 9-13: Sail on our Public Sailing Cruises that depart from the US Sailboat Show! Cruises are one and a half hours long. Rates: $30 for Adults and $25 for children. (not including admission into show) More Detailed Info

October 12, Sunday: Specialty Cruise: “Brews in the Breeze” Lunch Cruise. Join the fun on an afternoon of beer tasting along with a delicious lunch. After we raise all our sails, we will start the tasting with the lightest of the four beers. Lunch will consist of all your Chesapeake favorites served buffet style while sailing on the beautiful Bay! Cruise departs from Annapolis City Marina.  More Info…

October 14-21:  Special Cruises below offered and Private Cruises can be booked and are encouraged.

October 16, Thursday: Specialty Cruise: “Chesapeake Bay Schooner Race Watch Cruise” Sail aboard Woodwind II as we cheer on Woodwind and over 40 other schooners while they start the 130 mile race down the Bay. Cruise departs from Annapolis City Marina. More Info…

October 18, Saturday: 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. More Info…

October 19, Sunday: Specialty Cruise: “Champagne Brunch”. Join the best bubbly brunch on the Bay. Enjoy sparkling wine, and two other champagne cocktails accompanied by delicious food and always entertaining company! Cruise departs from Annapolis City Marina.  More Info…

October 23, Wednesday: Public, 2-hour, Sailing Cruises resume at the Annapolis Marriott Waterfront Hotel. More Info…

October 26: Last Day of Public Cruises More Info…  Private Cruises can be arranged until November 1.

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