Multi-Day Cruises

 Overnight Cruises on the Chesapeake Bay

Great Chesapeake Bay Schooner Race

Schooner Race from Annapolis, MD to Norfolk, VA – SOLD OUT

  • October 16-20, 2019
  • $900 plus tax per person

Race down the Chesapeake Bay on one of the fastest schooners! We set sail on Wednesday, October 10 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 to Norfolk, VA. On Saturday afternoon there is a party filled with sea shanties, 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 season! We have won our class many times, and have won the overall trophy three times. We are very competitive and love to teach 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. More details…

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

5-Day Adventure Cruise: Norfolk, VA to Annapolis, MD –  SOLD OUT

Join the Schooner Woodwind for a 5 Day Adventure Sail on the Chesapeake Bay October 15-19, 2012

Schooner Woodwind docked at the Calvert Maritime Museum in Solomon’s Island

  • October 21-25, 2019 (Monday- Friday)
  • $1800 + tax per cabin (2 people) or $1650 + tax per cabin (1 person)

This fall, take a cruise up the Chesapeake from the Norfolk area in Virginia to Annapolis, MD as Woodwind returns after completing the Great Chesapeake Bay Schooner Race. This cruise can accommodate four couples to sail on our five day, four night cruise aboard the classic schooner. We will be sailing more than 130 miles up the Chesapeake Bay during the fall foliage season in mid-October.

You can purchase individual cabins for the 5-Day Cruise.

Norfolk Annapolis Sailing Cruise Schooner WoodwindWe encourage you to participate in all aspects of sailing. No experience is required. We will teach you the basics of sailing and navigation or you can just relax and enjoy the scenery.

Our itinerary has to be flexible! Secluded coves and quaint towns & villages await our exploration.

Places We Have Visited On Previous Cruises:

  • Onancock, VA
  • Irvington, VA
  • Reedville, VA
  • Deltaville, VA
  • Oxford, MD
  • Soloman’s Island, MD
  • La Trappe, MD
  • St. Michaels, MD
  • Galesville, MD

All of our destinations depend on the weather, wind speed and direction. This is a sailing adventure with a great crew on a wonderful boat.

Included in this trip are:

  • All meals and snacks, (except one dinner ashore)
  • Accommodations aboard
  • Captain and crew
  • 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!

See photos from past cruises

Call 410-263-1981 or email us with any questions.

The Interior Layout of Woodwind

Schooner Woodwind Interior Below Decks

Click on Image for larger version

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.

Dining Area

Guest Stateroom



Call 410-263-1981 to book any of our Multi Day Cruises.

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