Multi-Day Cruises

 Overnight Cruises on the Chesapeake Bay

Join Our Team for the Great Chesapeake Bay Schooner Race featuring 2 boats sailing

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

  • October 6-10, 2021
  • $1000 plus tax per person

Race down the Chesapeake Bay on one of the fastest schooners! We set sail on Wednesday, October 6 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 10:30 am  (we got to get the boat back up to Annapolis).

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.

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.

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