“Woodwind” sails up to four times daily throughout the Sailboat Show October 4th – 8th from Dock “E2″. Each trip is unique. All cruises depart from the Sailboat Show and pass by the United States Naval Academy and then into the Chesapeake Bay. Sailing across the Chesapeake Bay is a fabulous experience as are the breathtaking sunsets over the historic Annapolis skyline.
Let our captain and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.
Our cash bar is stocked with wine and beer, including a nice selection of local micro-brews, soda and water. We also sell bagged snacks aboard.
The 74-foot schooner “Woodwind” was custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as “yachts” in the early part of this century. Her handsome mahogany brightwork, gleaming chrome and roomy cockpit distinguish her from cargo carrying work vessels.
Or… just take a tour of the schooner when we are dockside.
What is the Sailboat Show?
1: You must buy a ticket into the Boat Show in order to sail with us.
Tickets to the boat show may be purchased at the gate or online in advance, here.
Boat Show Admission Tickets:
Thursday: VIP DAY $35
Friday – Monday: $17 Adults, $4 Children (7-12) 6 and under, free!
Click here to buy entry tickets for the Boat Show!
2: Buy A Ticket to Sail on Woodwind
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Come into the Boat Show (remember you need a ticket for Boat Show) as early as possible.
- Go directly to “E2″ Dock (North T-Head) to buy your tickets from our staff for the time you would like and then enjoy the show.
- Click here for a Layout and Map of the Boatshow: on Dock E2 (North T-Head). (Boat Show Map)
- Click on thumbnail to right for a Layout Map with Woodwind on the map.
- We board 15 minutes prior to sail.
- No phone calls to purchase tickets due to our temporary location.
- Tickets can only be purchased in person on the day you want to go sailing.
Cash or Credit Card only.
3: Enjoy your Boat Show Experience
- Wear soft soled shoes and layered clothing.
- With your admission ticket, you can go on most of the boats that are exhibiting to take a closer look. (They may even ask you to take your shoes off.)
- This is also a great place to get good deals on raincoats, sunglasses, portable coolers, books, calendars and so much more.
4: Allow plenty of time for traffic and parking!
This is a huge event in the city of Annapolis. Some parking lots are not used for parking due to the Boat Show.
Click here for all the boat show information including parking tips!












