Annapolis Sailing Cruises Around the Chesapeake Bay Aboard the Schooner Woodwind.

Woodwind Offers...

2-Hour Public Sailing Cruises
"Woodwind" sails up to four times daily throughout our summer season from the Annapolis Marriott Waterfront Hotel. Each trip is unique. All cruises sail by the United States Naval Academy and then into the Chesapeake Bay. Sailing under the Chesapeake Bay Bridge 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.

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.

Have a group of 18 passengers or more? You can get your tickets further in advance and pay the gratuity up front. Click here for our Group Sail Brochure.

Sunset Sails & Entertainment

The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight. Our popular sunset sails start in May. Weekday sunset sails include the following events or entertainment.

Mon.

Tues.

Wed.

Thurs.

Historic Mondays Historic oriented guided tour from the water

Beer Tasting Sample
3 different local and regional microbrews

Race Woodwind vs. Woodwind II as we start just after AYC series with over 100 boats!

Local Musicians NightChesapeake Bay inspired music
Calendar of musicians

Rates & Schedule
Tickets go on sale six days in advance

Wednesday Night Race Series

Woodwind and Woodwind II will be match racing every Wednesday night that there is an AYC Race. Both boats will start on the AYC starting line at 6:45pm, and then race out to a slightly different race course, probably a little longer. During the race, passengers ("guest crew") will be able to participate in helping to sail the boat and steer the boat, when appropriate of course. This will be America's Cup style racing since it is match racing, so the competition will be very strong between the father and daughter teams who are the captains of each Woodwind.

"Party Like A Sailor!" Mount Gay Rum is partnering with us to offer you the most authentic sail boat racing experience. Aboard each Woodwind, we will be serving Rum Punch, and giving out two tee-shirts to each boat with a raffle. Scramble to find your Mount Gay Rum Red Regatta Hat, or borrow a friends, and get your first rum punch for free! Upon leaving the Woodwinds' after the exciting race, you will receive a Mount Gay Rum free drink voucher to be used at the Boatyard Bar & Grill a few short blocks away. This is the place where they will be showing the videos of that nights racing on the flat screens in the bar and restaurant. Enjoy the camaraderie of all the fellow racers that gather here as the sailor's place to be! Their food is great, too!

Tickets are the same price as our weekly sunset sails, $37 adult, $22 children under 12 and include a soft drink and a snack. Tickets go on sale six days prior to the date you want to go sailing.

Racing starts on April 28, with the last race on September 8. No racing on July 7.

Phone 410-263-7837 for more information.

Tickets go on sale six days in advance

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