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Wednesday Night Sailboat Races on the Chesapeake Bay

“Jibe. Jibe. Jibe. Jibe. Watch your head. Jibe…Ok, great. We’re probably going to tack again in a few minutes. Keep an eye on them!”

Captain Jen’s directions flew over the heads of the passengers to the crew as the sails filled with warm August breeze, and our schooner, Woodwind II, picked up a little more speed.

Captain sailing boat with another sailboat in the distance
Captain Jen keeping an eye on the competition

Even as the faint colors of sunset began to appear on the horizon, the day’s heat still hung heavy on the Chesapeake Bay. On shore, people were beginning to wind down their day, but our excitement was just beginning.

It happens this way every Wednesday in the summer in Annapolis, Maryland. In the late afternoon, over 100 yachts flood into the bay, preparing for the races. At 6:00pm near the mouth of Spa Creek, the first race begins. On the water, on the nearby Spa Creek drawbridge, and at various points along the bay, spectators gather to watch the competitions. Every few minutes, different classes of boats take off in their respective fights for the bragging rights for the next week.

Boats in the Chesapeake Bay in Annapolis, Maryland
Other boats in the bay

It was 6:45pm when the horn blared, signaling the beginning of the contest between the schooners Woodwind and Woodwind II. On the Woodwind II, we got off to an early lead, three or four boat links ahead of our sister vessel. Although we were just temporary guests on the boats, we instantly felt an allegiance to our boat and her captain, who was racing against her father for the fifteenth time this summer.

Captain sailing sailboat
More moves to get ahead

The competition stretched nearly two hours, with the Woodwind II leading for much of the race. The contest alternated between absolute calm (when we enjoyed the peacefulness of the bay and sipped rum punch) and furious activity (when we scurried from side to side, shifting the boat’s weight to help us gain speed).

Schooner with many passengers sailing on water
Angling for the best spot

Shortly after we rounded the downwind mark (i.e., turned around to head for the finish line), the schooner Woodwind inched up to overtake us. It passed so close that a crew member from each boat reached out and gave the other a high five – definitely a moment of peak excitement in the race as the Woodwind blazed past.

Schooner Woodwind boat passing a red race checkpoint
The Woodwind gains steam rounding the downwind mark

But Captain Jen, the crew, and our group of nearly 50 passengers weren’t going to let that stand. After a few more rapid maneuvers by the crew and much more scurrying by the passengers, we took the lead for the final time, sailing across the finish line as the sun dipped below the horizon.

The end of the race doesn’t mean the end of the evening. Crew and passengers adjourn to the Boatyard Bar & Grill to watch the video of the races and enjoy some well-earned snacks (and a bit more rum). After some good-natured ribbing of the losers and a few toasts to a great night, it’s time to turn their attention to the next sailing.

People at a bar in Annapolis
Festivities following the races at the Boatyard

Sailing on the Schooner Woodwind and Woodwind II

Race dates: Usually late April through early September
Race tickets: $46 for adults and $29 for children under 12. A soft drink and snack are included, and alcoholic beverages are available for purchase onboard
Location: Docked at the Annapolis Marriott Waterfront Hotel (80 Compromise Street); go through Pusser’s Caribbean Grille to the water
Timing: Arrive by 6:15pm

There are many other options for sailing on the Woodwinds, which can be found on their website.

We were the guests of Annapolis Sailing Cruises: Schooner Woodwind and Visit Annapolis. All opinions of the exciting and windy are our own.

Sailboat on the water at sunset

Would you participate in a boat race like this?

Sailing on the Chesapeake Bay

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