Every Tuesday evening through September, a stretch of Back Creek in Annapolis fills with kayaks, paddleboards, and small boats, all pointed toward the same unlikely stage: a 40-foot-plus catamaran anchored offshore with a band playing on its deck. The free concerts, known as Tunesday, turn the waterway into an open-air venue where the audience floats instead of sits.
The series is hosted by Chronic Sailing, and it was covered this week by Alex Parker for WBFF, which highlighted concertgoers arriving by paddleboard, kayak, and boat to catch the show. According to Eye On Annapolis, the 2026 lineup runs from May through September and begins 90 minutes before sunset each Tuesday, featuring local acts including Ryan Keith, Jimi Haha, DJ Crawdads, The Betas, Sydney Smith, and Higher Hands.
A Captain Who Doubles as the Bandleader
Chronic Sailing was founded by Annapolis musician and ASA-certified sailing instructor Captain Shawn Owen, a USCG 100-ton Master Captain who completed an Atlantic crossing during the Clipper Round the World Race in 2022, according to SpinSheet Magazine. Owen opened the business out of Port Annapolis, offering boutique charters, bareboat rentals, and sailing instruction alongside the concert series he built around his own musical background. That dual identity, captain and performer, is baked into how the Tuesday shows work, with the floating stage doubling as one of the company's chartered vessels.
The business has also earned broader institutional recognition. The U.S. National Park Service designates Chronic Sailing as an official Chesapeake Gateways Experience, noting that it delivers educational charters covering Chesapeake Bay history, ecology, and landmarks such as the Thomas Point Shoal Lighthouse. That designation ties the weekly concerts to a larger network of public access sites and heritage experiences across the region.
Watching From Land or by Water
Not everyone needs a boat to take part. Spectators can watch from land at Ellen O. Moyer Nature Park along Back Creek, including the park's public dock, per Eye On Annapolis. The 12-acre waterfront park is managed across Back Creek by the Annapolis Maritime Museum & Park, giving non-boaters and non-paddlers a front-row view without ever leaving the shore.
For those who do want to get on the water, local outfitter Capital SUP offers dedicated paddleboard and kayak rentals on Back Creek built specifically for paddlers heading out to the floating stage. The rental partnership shows how a single weekly concert has grown into a small commercial ecosystem, with Capital SUP's waterfront locations feeding paddlers directly into the Tunesday crowd.
Rules of the Water After Dark
A crowded evening waterway carrying motorboats, kayaks, and paddleboards toward the same anchor point comes with real regulatory stakes. Under Maryland Department of Natural Resources boating rules, stand-up paddleboarders and kayakers must carry a U.S. Coast Guard-approved wearable life jacket for every person aboard, and children under 13 must wear one at all times on vessels under 21 feet, according to BOATERexam.com. Paddleboarders are also required to carry a sound-producing device such as a whistle while on state waters, and Maryland strictly enforces Boating Under the Influence laws with a legal blood alcohol limit of 0.08%, per the Professional Stand Up Paddleboard Association, which notes that Natural Resources Police monitor local waterways to prevent impaired boating.
Powerboat traffic sharing the channel is regulated too. Maryland law requires all motorized vessel operators born on or after July 1, 1972, to hold a state-issued Boater Education Card, a certification requirement that applies to any numbered or documented motorboat on state waters, BOATERexam.com notes. With paddlers, boaters, and a large anchored catamaran converging in the same narrow stretch of creek at dusk, that rule matters as much to concertgoers as the setlist.
A Creek With a Working Past
Back Creek's waterfront wasn't always a concert venue. The historic campus at the water's edge sits on the site of the McNasby Oyster Company, established in 1886 as Annapolis's last remaining oyster-packing plant before it was restored into a maritime museum in 2000. The site suffered major damage from Hurricane Isabel in 2003 before fully reopening in 2008, a history that traces the creek's shift from a 19th-century commercial seafood hub to today's recreational draw.
Tunesday also isn't the only game in town this summer. Chronic Sailing's Tuesday series runs alongside the Annapolis Maritime Museum's Tides & Tunes waterfront series, which holds free shows on Thursday evenings in Eastport, and Maryland Hall's BloomHaven series, which hosts outdoor lawn concerts on weekends. Together, the three series have turned Annapolis's summer calendar into a near-nightly rotation of free live music across the city's waterfront and lawns.
