From the Bay, From the Bay to the Blue Ridge

Sailing on the Woodwind

Russ Branton racing on a Wednesday night on the Woodwind.
Russ Branton racing on a Wednesday night on the Woodwind.

The week she moved to Annapolis 19 years ago, Susan Helbert was strolling along the water by Pussers Caribbean Grille at the Marriott and discovered the Schooner Woodwind at the dock. Although she had done some boating, she had never been sailing before, so she bought a ticket and hopped onboard for a sunset sail. “It was so windy and gorgeous, I was hooked,” she says. “Between that early week of August and the end of the season, I sailed on Woodwind 19 times.”

Frequent Sailor Susan, as dubbed early on by the crew, has sailed more than 500 times on the 74-foot schooner. In addition to sunset sails, Susan has sailed on Woodwind for many specialty cruises—lighthouse and fireworks cruises, dinner and beer-tasting cruises—as well as for the Great Chesapeake Bay Schooner Race (GCBSR) and five-day trip home from Portsmouth, VA, a few times.

Math swirling in my head, I had to ask: why didn’t she just buy a boat? Susan says, “At the time, boats were depreciating, but houses weren’t, so I bought a house. I knew Woodwind would be there.” You can’t argue with that—but I went a step further and pulled out the calculator. If you divide 500 sails by 19 years, that equals about 26 sails per year. By today’s sunset sail pricing ($42 per trip), averaging in the occasional specialty sail and schooner race that cost more, the total comes to less than $2000 per year for a whole lot of sailing.

Be honest—how many Chesapeake sailboat owners take their big boats out as many as 26 times per year? How many have spent less than $2000? Susan is no dummy.

Russ Branton and Joyce van den Berg of Princeton, NJ, who both grew up sailing and boating, write, “Since we don’t live on the water now, we enjoy weekend getaways to Annapolis and other coastal locations. The first thought when arriving to a sailing town is always, ‘Wouldn’t it be great to go sailing?’ We had no idea during that first visit in 1997 that sailing a 74-foot schooner was possible.”

The couple has sailed more than 30 times on the Woodwind or her twin sister ship Woodwind II, often for Wednesday night sailing races. “Captains Ken and Jen Kaye [father and daughter] are ultra-competitive, and it’s our favorite time to sail.”

“The absolute highlight of our sailing experience on Schooner Woodwind was last fall’s GCBSR… We finished first across the line in 22.5 hours and won first in class and first overall on corrected time. It was an absolutely great race on a very fast boat with the super-experienced team.”

Like the others, Carolyn Cordrey and her sister Julie hopped aboard the schooner on a whim. “It sounded like a fun afternoon,” she says. For her, it was a “magical and life-changing experience.” The deckhand who helped her board, Matt (“love at first sight”) Cordrey, became her husband two years later.

Carolyn says her first schooner sail was her gateway to realizing her dream of coastal living. The Cordreys honeymooned on his parents’ Sabre, and her hubby taught her the ropes. The couple and their two children, Madeline (5) and Vivienne (2) go sailing as often as they can. “It’s our favorite way to spend time together as a family,” says Carolyn, who likes to entertain her kids by telling them that their daddy was a pirate when she met him.

“What sets apart the Woodwind team is that the crew members have as much fun as their guests. They are crewing for the love of sailing, and they share that passion with everyone who comes aboard,” she says.

Among the things faithful Woodwind sailors wished more people knew about the experience—that it’s cooler on the water, that you don’t need any experience to try it, that it’s stress-relieving—crew members treating guests like close friends and family topped the list. “They are very kind people,” says Frequent Sailor Susan. “That to me in this day and age is an absolute necessity… They are family to me. When I am not here, I miss them.”

Written by: Molly Winans

To learn more about sailing on the Schooner Woodwind, visit

You’re Invited:
OTC readers interested in getting into sailing this season are invited to attend SpinSheet’s free Start Sailing Now Q&A and Crew Party Sunday, April 27, at the Annapolis Maritime Museum. The Q&A with local experts runs from 3-4 p.m., and the party, with live music, free beverages, and a lot of sailing stories, runs from 4-6 p.m.

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