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Sailing Cruises around the Chesapeake Bay

Destination Cruises...
St. Michael's and Cantler's Crab House

The 74-foot Schooner Woodwind sets sail for longer day trips to fun destinations around the Chesapeake Bay each month. These cruises depart from Annapolis, stay in the port of call for a couple of hours and then sail back to Annapolis.

St. Michaels, MarylandSt. Michaels- a quaint Chesapeake seaport town has so much to offer visitors. The boat will drop you off inside the terrific Chesapeake Bay Maritime Museum, where exhibits of boat building, duck decoys history and the history and chronology of Chesapeake Bay boats will delight you. If you walk into town, you will find a wonderful collection of shops, restaurants, gorgeous homes and bed and breakfasts. More... May 18

Cantler's Crab HouseCantler's Crab House- a crab lover's dream place! This restaurant is known for its shellfish. Crab and work boats are tied up at the docks as we come in. It is located on Mill Creek outside of Annapolis. As we navigate into the small channel, you will see ospreys nesting on most of the channel markers and gorgeous mansions along the shoreline. Our crabfeast includes all-you-can-eat crabs and steamed shrimp with corn-on-the-cob, cole slaw, french fries, onion rings and soft Special Event Scheduledrinks. More... October 18

Specialty Cruises:
Lighthouse Tours and Wine Tastings
Thomas Point Lighthouse

Lighthouse Tours- A four hour sail to as many as four different lighthouses on the Chesapeake Bay. Learn about their history, importance, and present day condition by a speaker from the U.S. Lighthouse Society-Chesapeake Chapter. More... April 27, July 13, October 19 Wine Tasting while sailing

"Wine in the Wind"- Wine Tasting while sailing! A three and a half hour sail around the Bay sampling wine. A representative from the wineries will be aboard to coordinate tasting. This will be a relaxing sail including afternoon appetizers and four samples of wine. More... June 22, July 20, August 10 and Sept. 21

Download Special Events Schedule as a .pdf


    Overnight Cruises on the Chesapeake Bay

    5 Day Cruise from Portsmouth, VA to Annapolis, MD

    1998 Norfolk-Annapolis Group having fun!This fall, take a cruise up the Chesapeake from Norfolk to Annapolis as Woodwind returns after completing the Great Chesapeake Bay Schooner Race. Woodwind offers the chance for four couples to sail on a five day, four night cruise aboard the classic schooner. We will be sailing more than 130 miles up the Chesapeake during the peak of fall foliage in late October.


You can purchase individual cabins for the fun 5-Day Cruise
This is the only cruise sold by the cabin.
We encourage you to participate in all aspects of sailing Woodwind. No experience is required. We will teach you the basics of sailing, cruising and navigation or you can just relax and enjoy the scenery.

Our itinerary is always flexible! It will probably include a secluded cove in the LowerWoodwind at Solomon's Island Bay, then Solomons Island, and then perhaps a sail to Oxford on the Eastern Shore. There are so many fantastic places to visit as we journey up the Bay towards Annapolis. We have visited places like Onancock, Reedville, Deltaville, La Trappe, St. Michaels, Galesville, and many other fantastic ports. All of our destinations depend on the weather and the wind, which is usually gorgeous this time of the year.

Included in this trip are all meals (except one dinner ashore), onboard accommodations, captain and crew, and non-alcoholic beverages. Dockage and gratuity are not included. Space is limited to four couples. See photos from past cruisesThis one-way sail up the Bay should not be missed!

October 20-24 Monday- Friday
The price is $1600 per cabin
(for two people).
410-263-8619 or email us with any questions.

The Interior of Woodwind

Interior Layout of WoodwindThe layout of Woodwind has 6 private double staterooms (cabins) all with double sized berths. The guest cabins are all located in the separated forward cabin area accessible by a separate companionway (stairs). This area provides 2 heads with built in showers. Each cabin has a complete set of sheets, blankets, pillows and towels. All staterooms have opening ports (windows) and the two most forward cabins have opening hatches as well. There is a seat and hanging locker in each area with space for storing a soft duffel. All cabins have standing headroom for dressing. The large dinette or the comfortable cockpit can seat 10 for breakfast and lunch. There is a fully equipped galley and separate captain and crew quarters.

Galley area
Dining area
Guest stateroom

Special Event Schedule
This Week's Schedule
About Woodwind and Woodwind II

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