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.
Available Now
Spirits & Spirits
-Annapolis-
Select Fridays July-September
During this walking tour and cruise combination experience, you’ll brave the Historic District by foot and then continue on through the haunted waterways of Annapolis.
Bay Lighthouses Cruise
-Annapolis-
Click “Book Now” for available dates.
Pass under the twin spans of the Bay Bridge and past three Chesapeake lighthouses: Sandy Point Shoal, Baltimore Harbor, and Thomas Point on this award-winning 3- to 3½-hour cruise.
Rock the Harbor with Tranzfusion
-Annapolis-
September 29, 2023
Tranzfusion is back by popular demand for a 2.5-hour live music cruise in Annapolis!
Yoga on a Yacht
-Baltimore-
October 8 & 22, 2023
We’re teaming up with Baltimore yoga instructor Marissa Walch for Yoga on a Yacht! Grab your mat and climb on board for a Sunday morning flow.
Naptown Brass Band Cruise
-Baltimore-
October 13, 2023
Enjoy a 2-hour cruise with live music by The Naptown Brass Band, this time in Baltimore!
Fall Foliage Bay Lighthouses Cruise
-Annapolis-
Select dates in October 2023
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-
November & December 2023
Annapolis’ favorite holiday activity makes its return for the 2023 holiday season. Enjoy hot cocoa, holiday music, and good cheer!
Coming Soon
Dog Days of Summer Cruise
-Annapolis-
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.
Full Moon Cruise
-Annapolis-
Climb aboard to watch the sun set and the full moon rise over the water as you sip a cool cocktail and relax to live music.
Naptown Brass Band Cruise
-Annapolis-
Enjoy a 2-hour cruise with live music by The Naptown Brass Band, a New Orleans style street band that is taking Annapolis, Baltimore and Washington by storm.
New Year’s Eve Cruises
-Annapolis & Baltimore-
Ring in the New Year on an exclusive and fun fireworks cruise aboard a luxury yacht with a DJ, dancing, desserts, and a complimentary glass of champagne.
Father’s Day on the Bay to St. Michaels
-St. Michaels-
Enjoy Father’s Day with a cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore.
Fireworks Cruises on July 3rd & 4th
-Annapolis & Baltimore-
Enjoy the spectacular fireworks displays from the best seat in town!
Annapolis Sunset Cruise with Live Music
-Annapolis-
Enjoy live music and beautiful scenery as you relax with a cool drink on this 90-minute sunset cruise in Annapolis.
Cruise to the Watermen’s Festival
-St. Michaels-
Cruise roundtrip to the Annual Watermen’s Appreciation Day in St. Michaels on Maryland’s Eastern Shore.
Chesapeake Bay Trio
-Annapolis-
Join our live interpreter for an enjoyable 3-hour cruise from Annapolis’ historic harbor, up the scenic Severn River, then into the Chesapeake Bay, under the Bay Bridge, to Thomas Point Lighthouse.
Critter Cruise
-Annapolis-
Get the kids out on the water to for a fun, hands-on learning experience with critters in the Chesapeake Bay. Ideal for grades 1-5.