Annapolis Sunset Cruise with Live Music
Dates Available
Friday Nights
Price
$43/and upLocation
Annapolis
Upcoming Dates
Fri 6:30 pm - 8:00 pm
Book NowDescription
Enjoy live music and beautiful scenery as you relax with a cool drink on this 90-minute sunset cruise in Annapolis. Beverages and snacks are available for purchase from our full bar. Presented by:
2026 Annapolis Sunset Cruise with Live Music Lineup
- Friday, September 4 – Naptown Brass Band
- Friday, September 11 – Songwriters on Severn
- Friday, September 18 – Tommy Perrell
- Friday, September 25 – Rick and the Revolving Doors
Find more live music cruises and special events here!
Performances are subject to change.
Watermark's Friday Night Live
Sunset Music Cruise Series
In Partnership with WRNR 93.5 FM
Naptown Brass Band
Friday, September 4
The Naptown Brass Band—voted Best Local Band by What’s Up Annapolis Magazine (2023, 2024, 2025)—brings the energy and soul of New Orleans to Annapolis, Baltimore, and Washington, D.C. With infectious grooves, bold brass, and second-line spirit, they turn every cruise into a lively, unforgettable celebration. Whether performing on deck or leading guests in a parade-style experience, Naptown creates a fun, high-energy atmosphere that gets everyone moving. When Naptown comes aboard, the party follows.
Tommy Perrell
Friday, September 18
Tommy Perrell is a Maryland-based multi-instrumentalist with 20 years of performing experience. Covering everything from the 60s to today, Tommy brings a diverse mix of classic rock, country, and modern favorites to every show. A seasoned performer, songwriter, and studio musician, Tommy delivers an energetic set packed with songs audiences know and love.
Rick and the Revolving Doors
Friday, September 25
Rick and The Revolving Doors is known as a fun, high-energy party band. Each gig is an inclusive celebration of music and dancing led by John Sellman’s charismatic personality. The band is available to book for Weddings, Corporate Events, Restaurant Gigs, and more!
No pets on this cruise please! Visit our FAQ page for more information.
Departure Location
The Piers at 1 Prince George Street
1 Prince George St, Annapolis, MD 21401
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