October is a wonderful time of year to sail.
- Typical breezy conditions
- Cooler temps
- Fall Foliage turns mid-October
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 5 – October 14: No Public Cruises. Private Cruises can be booked and are encouraged.
October 15, Thursday: Special Event: “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. The cruise departs from inside the US Sailboat Show Dock F2
Buy Tickets here: https://schoonerwoodwind.com/event/schooner-race-watch-2026/
October 15-18: 1.5 Hour Public Cruises departing up to seven times daily from inside of the Sailboat Show. Get your “Woodwind Combo Tickets” where we package the cruise and one day Boat Show Admission together! This deal discounts the one day Show Admission ticket by up to 40% when purchased online. SAIL BOAT SHOW CRUISE INFO & TICKETS
October 19-21: No Public Cruises. Private Cruises can be booked and are encouraged.
October 22, Thursday: Public, 2-hour, Sailing Cruises resume at the Annapolis Waterfront Hotel. More Info…
October 31: Last Day of Public Cruises More Info…