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 1-4: 2 Hour Cruises departing the Annapolis Waterfront Hotel (our normal operation). BUY TICKETS
October 5-7: No Public Cruises. Private Cruises can be booked and are encouraged.
October 8-12: 1.5 Hour Public Cruises departing up to four times daily from inside of the Sailboat Show. Get your discount on packaging the cruise and Boat Show Admission together! Sail Boat Show Cruise Info & Tickets
October 11, 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. Info, Menu & Tickets
October 13-20: Special Cruises below offered and Private Cruises can be booked and are encouraged.
October 15, 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. Info, Menu & Tickets
October 17, 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. Info, Menu & Tickets
October 21, Wednesday: Public, 2-hour, Sailing Cruises resume at the Annapolis Waterfront Hotel. More Info…