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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- 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 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
drinks.
More...
October 18
Specialty
Cruises:
Lighthouse Tours and Wine Tastings

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
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
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.

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 Lower
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.
This
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
The
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.
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