Schooner Woodwind

  • No trip to Annapolis, the Sailing Capital of the U.S., would be complete without sailing on the Chesapeake Bay.  Even if you have never sailed before, you will feel right at home on either of the two beautiful, wooden 74-foot schooners aptly named the Woodwind and Woodwind II that depart from the Annapolis Waterfront Hotel dock.  Their expert sailing crews guide trips along the historic Annapolis waterfront, past the Naval Academy and cruise into the Chesapeake Bay.  Depending on the strength of the wind, the schooners may make it all the way to the Chesapeake Bay Bridge during the tour!  You may be asked to become part of the "crew" and help raise the sails, or steer the boat.  Otherwise, simply sit back and relax.

    Consider a cruise for any of these occasions:

    • 2-hour public sailing cruises
    • Private Cruises
    • Schooner Races
    • Boat & Breakfast Overnight Experience
    • Team Building Events
    • Student Groups
    • Wine and Beer Events
    • Foodie Events
    • Multi-Day Cruises

    Guests of the Annapolis Waterfront Hotel receive exclusive VIP beverage service aboard the boat when booking a cruise. Upon check-in at the hotel you will receive a card for a complimentary Schooner Woodwind koozie and your choice of one local craft beer or a glass of wine.

    The Annapolis Waterfront Hotel and Schooner Woodwind have also partnered to provide a sailing season full of unique Sunday getaways. Select a Sunday Cruise including a wine tasting, live music, brunch or the lighthouses of the Chesapeake Bay and then spend a relaxing evening at the hotel with special rates starting at just $179.

    Book Your Schooner Woodwind Cruise Now

    Book Your Annapolis Waterfront Hotel Stay Now


    Offers based upon availability and subject to change without notice. Schooner Woodwind cruise and hotel stay must be booked separately.

  • The schooners sail in all types of weather except lightning. Sailings are available April through October.  For more information and to book tickets, please visit www.schoonerwoodwind.com or call 410-263-7837.

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