Overnight Cruises on the Chesapeake Bay:

Schooner Race from Annapolis, MD to Portsmouth, VA

October 13-17, 2010
Race down the Chesapeake Bay on one of the fastest schooners! We set sail on Wednesday, October 14 to train all "guest" crew how to sail Woodwind on our way from Annapolis to meet up with the other schooners in Baltimore's Inner Harbor. After training we participate in a breathtaking Parade of Sail with all the other participating schooners- there were 54 last year with sails up and cannons firing. Wednesday night includes a "crew only" party for all the boats in Fell's Point. Thursday, the race starts just south of the Bay Bridge around 1:30 pm. We break into crew watches and sail the boat day and night until we reach the finish line at Thimble Shoal Light at the mouth of the Chesapeake Bay. Racing 130 miles down the bay can take as little as 12 hours and as much as 40 hours depending on the wind speed and direction.

Once across the finish line, we make our journey up the Elizabeth River past Norfolk to Portsmouth, VA. On Saturday afternoon there is a party filled with sea shantys, oyster and pig roast, beer truck, and the awards for the race. Parties go on through the night aboard the various schooners. There is a group breakfast for all crew on Sunday morning and we say goodbye around noon.

This is our favorite event all summer! We have won our class many times, and have won the overall trophy three times. We are very competitive and love to train the guest crew everything they need to know about racing. You will be responsible to stand watch and help out. All food and parties included while aboard the boat. $850 plus tax per person

Read more about past races and how we have done by clicking here.

5 Day Cruise from Portsmouth, VA to Annapolis, MD

All four cabins available! $1600 + tax per cabin (2 people).

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 18-22, 2010 Monday- Friday


The price is $1600 per cabin (for two people).
410-263-1981 or email us with any questions.

The Interior of Woodwind

The layout of Woodwind has 4 private guest staterooms (cabins) all with double sized berths. These 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.