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.
Annapolis Fireworks Cruises
July 3rd & 4th, 2022
Step aboard a Watermark boat for the annual Annapolis Fireworks Cruise to enjoy the fireworks displays from the best seat in town.
Baltimore Fireworks Cruises
July 4th, 2022
Enjoy the Baltimore skyline and spectacular Fourth of July fireworks from the best seat in town as you cruise the Inner Harbor.
Dancing Queen Cruise
August 5th, 2022
Mamma mia, here we go again! Climb aboard the Dancing (Harbor) Queen for this throwback cruise featuring a live DJ playing 70s and 80s hits.
Full Moon Cruise
August 12th, 2022
Climb aboard to watch the sun set and the full moon rise over the water. Sip a cool cocktail and relax to the tune of soft live music by Crosby Cofod.
Cruise to the Watermen’s Festival
-Annapolis to St. Michaels-
August 14th, 2022
Cruise roundtrip to the Annual Watermen’s Appreciation Day in St. Michaels on Maryland’s Eastern Shore. The festival celebrates Chesapeake watermen and their heritage.
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!
Baltimore Sunset Cruise with Live Music
September 3rd, 2022
This 90-minute Baltimore Sunset Cruise aboard a Watermark yacht takes you out on the water to watch the sunset to the tune of live music.
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.
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.
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.
Dog Days of Summer
An annual cruise to benefit the Anne Arundel County SPCA. Bring your favorite four-legged friend, leashed please, and have them bob for hot-dogs on the top deck.
Cruise to the annual Watermen’s Festival in St. Michaels on Maryland’s Eastern Shore. The festival celebrates watermen and their heritage. Fun for the entire family.
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.
Fall Foliage Cruise
This cruise includes three Chesapeake Bay Lighthouses and gives guests the spectacular view of the lovely fall foliage along the waterfront. A local favorite.
Jolly Express Cruise
Select dates December 2022
Hop aboard Miss Anne, all decked out for the holidays. Enjoy hot cocoa, holiday music, and good cheer on Captain Santa’s “sleigh ride.”
Lights Parade Holiday Package
Dine at the Severn Inn and enjoy a spectacular dessert cruise aboard our luxury yacht, Catherine Marie, to watch the Lights Parade.
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.