October Sailing Schedule

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 Waterfront Hotel so our cruises depart elsewhere.


October 11-18: Special Cruises below offered and Private Cruises can be booked and are encouraged.

October 13, 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 15, 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. SOLD OUT

October 16, Sunday: Specialty Cruise: “Brews in the Breeze” Enjoy Local, Craft Beer and a wonderful Maryland Lunch, complete with crab cakes.   Info, Menu & Tickets

October 19, Wednesday: Public, 2-hour, Sailing Cruises resume at the Annapolis Waterfront Hotel. More Info…

October 30: Last Day of Public Cruises More Info…  Private Cruises can be arranged through October.

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