2024 Sailing Season is coming! See you April 13, 2024!

Great Chesapeake Bay Schooner Race

Schooner Race from Annapolis, MD to Norfolk, VA
Click Here to Apply to be Guest Crew 

Race down the Chesapeake Bay on one of the fastest schooners!

  • October 2-5, 2024
  • Price $1250.00/guest Single Occupancy cabin + tax (sold by single occupancy cabin only)
  • Price $1150.00/guest Double Occupancy cabin + tax (sold by single occupancy cabin only)
    • Double Occupancy Cabins are for guests that know each other only

Wednesday, October 2:

  • Teach all “guest” crew how to sail Woodwind as we sail  from Annapolis to meet up with the other schooners in Baltimore’s Inner Harbor.
  • Parade of Sail in Baltimore Harbor (late afternoon)
  • “Crew Only” Party for all of the Schooners, volunteers and organizers.

Thursday- Friday, October 3-4:

  • Teach all “guest” crew more sailing techniques on the Woodwind as we make our way to just south of the Bay Bridge.
  • 1:30 pm Great Chesapeake Bay Schooner Race starts
  • We split 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.

Saturday, October 5:

  • Catch up on sleep
  • Great Woodwind Breakfast to celebrate our finish.
  • Party around 1:00 pm, with oysters and a pig roast, beer truck, sea chanteys, and the awards for the race.
  • Check into your hotel or other accommodation for Saturday night.  Check with the captain to find out what time your belongings need to be removed from the boat (this timing may vary based on weather conditions that will dictate what time Woodwind needs to depart Norfolk)
  • Other schooners may have parties that go on through the night or wander in town and catch up with the other crews.

Sunday, October 6:

  • “All Hands” Group breakfast for all schooner crew, volunteers, and organizers on Sunday morning.

This is our favorite event all season! We have won our class many times, and have won the overall trophy four times. We are very competitive and love to train the guest crew on 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.

See photos from our last race

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 a 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


Schooner Woodwind