Special & Seasonal Cruises

Annapolis & Baltimore

Climb on board for special & seasonal cruises!

Looking for fun things to do in Annapolis and Baltimore? Look no further! We plan special and seasonal cruises for holidays, city celebrations, area partnerships, and just for fun.

Don’t forget to check this page often, as we regularly add new events.

Available Now

Live music cruise aboard the Harbor Queen in Annapolis.

Annapolis Sunset Cruise with Live Music


Select Fridays and Saturdays May through September

Enjoy live music and beautiful scenery as you relax with a cool drink on this 90-minute sunset cruise in Annapolis.

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Spirits & Spirits


May-September 2024

During this walking tour and cruise combination experience, you’ll brave the Historic District by foot and then continue on through the haunted waterways.

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Naptown Brass Band Cruise


June 27, 2024

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.

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Fourth of July Cruises

-Annapolis & Baltimore-

July 3 & 4, 2024

Experience the incredible fireworks displays in Annapolis and Baltimore from the water!

Explore Cruises

Thomas Pt Lighthouse and Bay Bridge

Bay Lighthouses Cruise


July 15, 2024

Pass under the twin spans of the Bay Bridge and past three Chesapeake lighthouses on this award-winning 3- to 3½-hour cruise.

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Critter Cruise


July 25, 2024

Climb on board to explore the unique ecosystem of the Chesapeake Bay through this hands-on learning cruise ideal for grades 1-5.

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Yoga on a Yacht


July 28, 2024

We’re teaming up with Baltimore yoga instructor Marissa Walch for Yoga on a Yacht! Grab your mat, and climb on board for a morning flow.

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Coming Soon

Dog with sunglasses on a cruise

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.

Full Moon Cruise


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.

Fall Foliage Bay Lighthouses Cruise


This beautiful cruise includes three Chesapeake Bay lighthouses in addition to a spectacular view of the lovely fall foliage along the Annapolis waterfront.

Rock the Harbor with Tranzfusion


September 2024

Tranzfusion is back by popular demand for a 2½-hour live music cruise in Annapolis!

Jolly Express Cruise


November & December 2024

Annapolis’ favorite holiday activity makes its return. Enjoy hot cocoa, holiday music, and good cheer!

Lights Parade Dinner Cruise


December 2024

Join Watermark for a holiday dinner cruise aboard our luxury yacht.

New Year’s Eve Yacht Parties

-Annapolis & Baltimore-

December 2024

Make your New Year’s Eve memorable with a cruise aboard a luxury yacht! Enjoy a DJ, dancing, desserts, a complimentary glass of bubbly, and fireworks!

Mother’s Day Cruise


May 11, 2025

Treat the moms in your life to a lovely Mother’s Day brunch cruise.

Chesapeake Bay Trio


Select dates.

Join our live interpreter for an enjoyable 3-hour cruise from Annapolis’ historic harbor, up the scenic Severn River, then into the Chesapeake Bay.