+ By Christine Fillat + Photography by Tyler Loh & Benjamin Loh
of Wvndr Media
A certain kind of person chooses a life of sailing, music, or snowboarding. Somehow, for Shawn Owen, those three things go together. One frigid December day, Captain Owen and a small crew—his mate, the boat owners, and their friend—sailed out of Deale, heading for the US Virgin Islands to deliver a sailboat. They planned to sail offshore past Cape Hatteras and then continue on to the open sea. It promised to be windy, but in about four days, the weather would open up and be pleasant. Using a Starlink remote telephone service, Owen discussed Tunesday, his floating summertime concert series.
Owen and his family own Chronic Sailing, a charter, boat delivery, and sailing school located on Back Creek, out of Port Annapolis Marina. After time on the professional snowboarding and singer-songwriter scenes, Owen landed in Annapolis and has lived there now for many years. He has crafted a life encompassing all his passions. “Every now and then, I’ve worked it out to where, whenever I deliver a boat down to the Bahamas, [I] set up a small tour while I’m there, and stay for, like, a week or two and play music,” he says. “That’s just the bomb.”
Before the advent of the COVID-19 pandemic, Owen and percussionist Ben Bays would perform an acoustic set every Sunday at Pusser’s Dock Bar. But post-pandemic, Pusser’s didn’t renew its ASCAP and BMI music licenses and thus was no longer allowed to have live music on-site. So Owen tied his boat Sea to Sky, a 2014 Lagoon 42, to the dock at Pusser’s and started doing shows, powered by his own generator. This funky operation went well for a time, until Owen determined to shut it down to avoid ruffling too many feathers. He had to come up with another plan.
In the past, Owen played gigs with Capital SUP and its floating dock located off Ellen Moyer Nature Park. Chronic Sailing decided to try that formula with its fleet. “We wanted to have an acoustic band on the boat doing, like, a 90-minute set,” he says, “and people can paddle up and swim around and anchor their boats and just kind of chill and hang out.”
In 2024, Chronic Sailing anchored Starz, a2014 Lagoon 42 catamaran, on Back Creek, and throughout the summer hosted six gigs from the boat. It worked well. Trying to get the word out was difficult, but there was enough interest, and so they repeated the series in 2025.
The first Tunesday in 2025 was during the Blue Angels practice day in May, and Jordan Sokel, of Pressing Strings, performed. Skribe performed at the next show. “After that, we were just crushing it,” says Owen. Tunesday’s head count for the season ranged from 200 to 500 on over 100 boats, kayaks, and paddleboards. People could enjoy the music from water or land.
Tunesday doesn’t only provide a platform for music. In 2025, visual artists set up atop Starz and created plein air paintings. Local painter Amanda Guinn and some friends caught the ambiance on canvas. She will be curating visual artists for the 2026 season. Every concert will feature artists, and their artwork will be auctioned off at an end-of-season gallery party.
The 2026 Tunesday concert series is slated to run every Tuesday this year, from May 5 through August 25. Rain dates for weather-related concert cancellations will be in September. The May 5 show starts at 6:30 p.m. Start times for the shows will be in consideration of the sunset, allowing time for boaters to safely get off the water before dark. Chronic Sailing spoke with officials from the City of Annapolis to see if any permits were needed for the performances; as long as the shows are over by dark, they are in compliance with noise permits.
Performers from the 2025 season will be invited to play in the 2026 series, and Owen hopes to add more performers, perhaps showcasing two artists on certain nights. With his hands full piloting the boat and setting up the sound system, he will not be performing on Tunesdays. “We just want to support a lot of local, mostly original artists,” he explains.
Last year, Chronic Sailing partnered with Annapolis Baygrass Music Festival, a weekend event on the Sandy Point State Park waterfront. Musician Molly Tuttle and her traveling band recorded a music video featuring a cover of Ringo Starr’s “Octopus’s Garden,” and Baltimore-based band Geraldine recorded their original composition “In the Water” onboard Chronic’s boat Starz. These music videos will be used to promote the 2026 Baygrass festival (September 19–20). Owen is hoping to continue Sailboat Sessions with some of this year’s festival artists.
Owen is also considering expanding the concert series in the future to allow for extra dates, with day-style festivals for other locations such as Spa Creek, Round Bay, Magothy River, or West River.
Tunesday is funded through Chronic Sailing and sponsors. This year, it’s looking for tax-deductible professional sponsorships and private donations through its recently formed nonprofit, Chronic Cares.
These days, it isn’t likely one will catch a Shawn Owen Band gig. “I don’t tour much anymore,” he says. “I’ll play a bunch of acoustic shows, [or] I’ll go to the ski resorts in the winter and jam for the weekend. For the most part, I’m slowing down and taking things easy.”
As if delivering boats up and down the Atlantic Seaboard, captaining a sailing company, and heading up a weekly music series with a family at home is taking it easy! ν
For more information, visit chronicsailing.com/tunesday.
