Our special events are planned around the season, holidays, city celebrations, our area partnerships and just for fun!
Check this page often as we regularly add more Annapolis events (like music cruises!) and events in Baltimore. Our special cruises often coincide with Baltimore events and events in Annapolis like 4th of July Fireworks.
If something fun is happening on the water – or the sky – we’ll get you the best seat in town to enjoy it. Our Rock ‘N River cruises are a unique form of Annapolis entertainment and our Saturday night Annapolis Sunset Cruises with Live Music are one of the most fun things to do in Annapolis. Watermark has fun every day and these special cruises are all about fun.
Live Music Cruises
-Annapolis & Baltimore-
Click below to learn more about our upcoming live music cruises in Annapolis and Baltimore. Featuring local bands, a full bar, and spectacular views, these cruises really rock the boat!
Cruising Out Hunger
September 29th, 2022
Celebrate the actions that our neighbors throughout Anne Arundel County have taken to fight hunger in our community this September. Enjoy a sunset cruise on the Severn River onboard the Harbor Queen.
Rock the Harbor with Tranzfusion
September 30th, 2022
Tranzfusion is back by popular demand for a live music cruise in Annapolis! Tranzfusion, a classic rock band from Salisbury, Maryland, will rock the Harbor on Harbor Queen on this 2.5-hour cruise.
Bay Lighthouses Cruise
Select dates April-October
See Thomas Point Shoal, Sandy Point Shoal, and Baltimore Harbor lighthouses on Watermark’s award-winning 3 to 3.5-hour Bay Lighthouses Cruise.
Fall Foliage Bay Lighthouse Cruise
This beautiful cruise includes three Chesapeake Bay lighthouses in addition to a spectacular view of the lovely fall foliage along the Annapolis waterfront.
Jolly Express Cruise
Annapolis’ favorite holiday activity makes its return for the 2022 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute “sleigh ride” including hot cocoa, holiday music, and good cheer.
Lights Parade Holiday Package
December 10th, 2022
Dine at the Severn Inn and enjoy a spectacular dessert cruise aboard our luxury yacht, Catherine Marie, to watch the Lights Parade.
It’s our annual halfway to St. Patrick’s Day cruise. Dublin5, a local high energy Irish-rock band is an Annapolis favorite.
A great opportunity to get out on the water to see the start of the Great Chesapeake Bay Schooner Race. About 30 historic & modern schooners race to Portsmouth, Va. in this annual competition.
Chesapeake Bay Heritage
Enjoy beautiful shoreline scenery as our Maryland Certified Chesapeake Bay Storyteller connects you to the treasure that is the Bay.
Light City Cruises
View the festival lights from the water. This special themed cruise features music, light-up beverages, and spectacular views of Baltimore’s skyline.
Cruise to the St. Michaels OysterFest at the Chesapeake Bay Maritime Museum. OysterFest features live music, cooking demonstrations, children activities and more.
Cruise to the WineFest
Travel across the Bay to the St. Michaels Wine Festival. Enjoy wine tasting venues throughout the town. This cruise will sell out.
Fleet Week & Airshow
A signature Watermark event! There’s no better way to experience the U.S. Navy Blue Angels than from on a yacht as they buzz overhead.
Chesapeake Bay Trio
Join our live interpreter for a 3 hour cruise of Annapolis’s historic harbor. Enjoy local tales of the sea and cruise under the famous Chesapeake Bay Bridge.
New Year’s Eve Fireworks Annapolis Cruise
December 31st, 2022
Make your New Year’s Eve memorable with this exclusive and fun fireworks cruise aboard a luxury yacht. Desserts, dancing, music, and more!
New Year’s Eve Charm City Cruise
December 31, 2022
Ring in the New Year on an exclusive and fun cruise aboard a luxury yacht with dancing, desserts, and a live DJ.
4th of July Fireworks Cruises
-Annapolis & Baltimore-
July 3rd & 4th, 2023
Step aboard a Watermark boat for the annual fireworks cruise to enjoy the fireworks displays from the best seat in town.
Dog Days of Summer Cruise
Join us on Harbor Queen for a dog-friendly party on the water with our friends at the Anne Arundel County SPCA in support of their work.