Sailing Cruises: October 9-13 from the U.S. Sailboat Show


“Woodwind” sails up to four times daily throughout the Sailboat Show October 9th – 13th from Dock “F2″. 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, and 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… during the show (in between cruises) come aboard and just take a look on deck and below when we are dockside.

Sailboat Show Sailing Times

1: 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!

2: 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: $18 Adults, $5 Children (7-12) 6 and under, free!

Click here to buy entry tickets for the Boat Show!

 3: Buy A Ticket to Sail on Woodwind

  • Annapolis Sailboat Show Map

    Oct. 9-13 Boat Show Map Printable Version

    Come into the Boat Show (remember you need a ticket for Boat Show) as early as possible.

  • Go directly to “F2″ Dock to buy your tickets from our staff for the time you would like and then enjoy the show. We are near where you would get a Water taxi to the Brokerage Show.
  • We board 10-15 minutes prior to sail.
  • No online, telephone or advance ticket purchases during the Boat Show.
  • Cash or Credit Card only.

 4: Enjoy your Boat Show Experience

  • Have fun!!
  • Wear soft soled shoes and layered clothing.
  • With your Sail Boat Show admission ticket, you can go aboard most of the sail boats that are exhibiting.
  • This Boat Show is also a great place to get good deals on raincoats, sunglasses, portable coolers, books, calendars and so much more.
  • US Sail Boat Show’s website for more info.

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