October is a wonderful time of year to sail. Our sailing schedule varies from our normal schedule due to the Sailboat Show and Powerboat Show. We are displaced from our normal dock at the Annapolis Marriott Waterfront Hotel so our cruises depart elsewhere.
- Consistent breezes
- Cooler temps
- Fall Foliage turns mid-October
- Many super, special event cruises
October 1-3: No Public Sailing Cruises, Private Charters can be booked.
October 4-8: Sail on our Public Sailing Cruises that depart from the US Sailboat Show!
Cruises are a hour and a half long.
Rates: $30 for Adults and $25 for children.
More Important Info
October 7: Specialty Cruise: “Brews in the Breeze”. Join the Woodwind Crew for an afternoon of beer tasting along with a delicious lunch. Cruise departs from Annapolis City Marina. More Info
October 9-10: No Public Sailing Cruises, Private Charters can be booked.
October 11: 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 12: No Public Sailing Cruises, Private Charters can be booked.
October 13: 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 14: Specialty Cruise: “Champagne Brunch”. Join the Woodwind Crew for the classiest brunch on the Bay. Enjoy a very “bubbly” beverage selection, including sparkling wine, bellinis and other champagne cocktails. Cruise departs from Annapolis City Marina. More Info
October 15-16: No Public Sailing Cruises, Private Charters can be booked.
October 17-28: Public, 2-hour, Sailing Cruises resume at the Annapolis Marriott Waterfront Hotel. More Info
