Captain Jennifer Kaye; Captain of the Schooner Woodwind. Photos courtesy of Charlotte Faraci.

Schooner Woodwind has been a key part of Annapolis summers for 28 years. There are few things better than boarding one of the twin 74-foot, purpose-built ships at their dock on Ego Alley and taking a two-hour sail out along the Severn River.

Back in March, Captain Jennifer Kaye was gearing up to get her boats in the water on April 1, to begin the 2020 sailing season. Then Covid-19 happened. As a nonessential business, they couldn’t move forward with much of anything, not even moving their boats.

Facing the Challenges of Quarantine

The Woodwind under sail. Photos courtesy of Charlotte Faraci.

“We had one person working on the boats, just to keep them from depreciating,” she says. The other staff was furloughed. “We couldn’t allow them to go to work.”

It was a dark time, but she wanted to remind people that Woodwind was still there, even if they weren’t sailing. So she started experimenting. “When we were supposed to start sailing, I decided that we were going to keep up with all of our events,” she recalls. So they moved them online to Facebook Live.

They started off with a rum-themed cocktail party, and a virtual lighthouse tour led by Dave Gendell. They continued their weekly beer tastings with Port City Brewing in Alexandria, Virginia, and brought in musicians to play sets from home, like Gareth Asher, who played from his yard in Atlanta on Memorial Day.

Captain Jen. Photos courtesy of Charlotte Faraci.

“It was a lot of fun,” she says looking back. “We had a lot of viewers, and a lot of frequent sailors. It made me happy, and gave me purpose, as a business owner, to continue something.”

That said, they were thrilled when restrictions were lifted and they could actually get the boats back on the water. Then her focus moved to re-imagining how to provide a sailing experience while keeping physical distancing regulations in place.

Getting Back on the Bay

The prospect was daunting. “When I started looking at how far six feet is on the boat, it got scary,” she says. “We started with the captain. How many people can we fit in that cockpit? It’s a beautiful cockpit and it’s made for socializing, but not for COVID.”

It was the tape measure that dictated the rest, she says. The boats usually hold 49 guests but now sail with 24 max. Groups are seated in zones that accommodate different group sizes: two people on each side of the cockpit (A and D), six people seated together port and starboard in the center of the boat (B and F), and two groups of four up front (C and E).

Woodwind Zones. Photos courtesy of Charlotte Faraci.

“You can sign up with your group size and take over the space that matches it,” she explains. Due to the smaller passenger count, they have had to raise rates slightly, and eliminate senior and children’s pricing, as you’re paying for the allotted space on the boat. But, the result has been a hit for guests. “When they see the zones, they say, “Oh, this is smart. I’m so glad they’re doing it this way.”

Crew members wear face coverings for the entire sail, but guests have more flexibility. Masks are required for boarding, but once they depart and the sails are up, the captain invites those who wish to can take their masks off. “It’s whatever your comfort level is,” says Jen.

Woodwind is also still offering their beverage service, be it the complimentary soft drink with your entry ticket or beer, wine or bubbly available for purchase. Ordering is done through an app, and crew members announce themselves before they enter the zone for service, so people can mask up again if they wish.

Accepting the New Normal

And people are returning! They are happy to find a socially distant way to experience the beauty of the Bay. “The bachelorette parties are back, and we’ve had lots of families,” says Jen. “We’re also seeing more interest in private events, because we can do small weddings, we can do family reunions.” They can have 24 guests on private events. “The first question we’re going to ask is, do you need physical distancing? If they say yes, we’re going to say, what kind? Then it depends on what they need.”

Guests book online, but if you’re downtown and have a hankering for a sail, it’s worth going by their dock at Pusser’s. If a zone isn't filled by sail time, they’ll sell tickets for walk-ups, even if it means putting a smaller number of people in a larger zone. (Score!) Sails depart four times per day, at 11 am, 1:30 pm, 4 pm and 6:30 pm.

Sharing the Woodwind experience with anyone who wants to sail is key to her business model, Covid or no Covid. “If only two people come up, we’re sailing. We always have, since our second year in business.” Her reason is personal. “I want to make sure that people visiting Annapolis have something to do, and something wonderful to do and leave with a memory that is purely Annapolis.''

Click here to book your sail on the Schooner Woodwind.