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Annapolis Sunset Cruise with Live Music

Dates Available

Friday Nights

Price
$43/and up

Location

Annapolis

Upcoming Dates

Friday, August 21st

Fri 7:00 pm - 8:30 pm

Description

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

 

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

GroundRent

Friday, August 7

GroundRent - Baltimore's very own rock n' roll acoustic duo! Playing a mixture of upbeat covers and originals like local favorite, Baltimore, A’int the Beer Cold. It’s an all-out foot-stomping, acoustic jam!

Michael Miller

Friday, August 21

Rock / Top 100 Classic Rock, mixing in a little country.

Steven Dunn

Friday, August 21

Rickshaw Lizard

Friday, August 28

Rickshaw Lizard is a musical powerhouse on the rise in the Annapolis / Baltimore / Washington DC region. This jam-band has everything you want: smokin’ guitar licks, soulful sax, a funk-based rhythm section that will keep you moving, and four-part harmony vocals to set your soul alight.

Naptown Brass

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.

Rock Steady Project

Friday, September 18

Hailing from the heart of Washington, D.C., Rock Steady Project is a high-energy powerhouse, dedicated to keeping the authentic spirit of Go-Go music alive! Established in 2020, the band honors the pioneers of the genre through a vibrant fusion of R&B, jazz, funk and soulful percussion-driven rhythms. Known for our raw vocals, “pocket grooves and persistent danceable beats that deliver an immersive live experience! Our Vocalist blends velvety vocal harmonies with a slick modern production. Channeling the essence of the 70’s, 80’s, 90’s and present day. Originating in “Chocolate City” and guided by renowned conga percussionist “Rock Steady”! The band crafts a dreamlike atmosphere designed to inspire movement and energy. Adding flare, flavor, and the aesthetics to a show that you won’t forget. Allowing you to be sophisticated, sexy, and free all in one. Every talented musician in our band contributes a distinct element to this project. Remember we always begin to Rock Steady!

No pets on this cruise please! Visit our FAQ page for more information.