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.


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

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…   SOLD OUT

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…  SOLD OUT

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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