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.
September 29 – October 8: No Public Cruises. Private Cruises can be booked and are encouraged.
October 5, Sunday: Special Event: “Thomas Point Shoal Lighthouse Cruise”. Sail to Thomas Point Shoal Lighthouse and learn about its history, importance, and present day condition by guest lecturer David Gendell, author of “Thomas Point Shoal Lighthouse: A Chesapeake Bay Icon” & “The Last Days of the Schooner America: A Lost Icon at the Annapolis Warship Factory” The cruise departs from Annapolis City Marina.
Buy Tickets here: https://schoonerwoodwind.com/event/thomas-point-shoal-lighthouse-cruise-2025/
October 6-8: No Public Cruises. Private Cruises can be booked and are encouraged.
October 9-12: 1.5 Hour Public Cruises departing up to seven times daily from inside of the Sailboat Show. Get your Combo Tickets where we package the cruise and Boat Show Admission together! This deal discounts the Boat Show Admission ticket by up to 40% when purchased online. SAIL BOAT SHOW CRUISE INFO & TICKETS
October 13-15: No Public Cruises. Private Cruises can be booked and are encouraged.
October 16, Thursday: Public, 2-hour, Sailing Cruises resume at the Annapolis Waterfront Hotel. More Info…
October 16, 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 Annapolis Waterfront Hotel
Buy Tickets here: https://schoonerwoodwind.com/event/schooner-race-watch-2025/
October 31: Last Day of Public Cruises More Info…