Blue Angels flying over Baltimore

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. If something is happening on the water – or the sky – we’ll get you the best seat in town to enjoy it. And don’t forget to check this page often, as we regularly add new events.

Available Now

Rock the Harbor with Tranzfusion

-Annapolis-

April 26, 2024

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

Book Now

Annapolis Sunset Cruise with Live Music

-Annapolis-

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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Yoga on a Yacht

-Baltimore-

May 11, 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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Mother’s Day Cruise in Annapolis

-Annapolis-

May 12, 2024

Treat the moms in your life to a lovely brunch cruise this Mother’s Day featuring live music and an open mom-osa and champagne bar!

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Coming Soon

Dog with sunglasses on a cruise

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.

Thomas Pt Lighthouse and Bay Bridge

Bay Lighthouses Cruise

-Annapolis-

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.

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!

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.

Naptown Brass Band Cruise

-Annapolis & Baltimore-

Enjoy a 2-hour cruise with live music by The Naptown Brass Band.

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.

Spirits & Spirits

-Annapolis-

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.

Fall Foliage Bay Lighthouses Cruise

-Annapolis-

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 2024

Annapolis’ favorite holiday activity makes its return for the 2024 holiday season. Enjoy hot cocoa, holiday music, and good cheer!

Lights Parade Dinner Cruise

-Annapolis-

December 2024

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

New Year’s Eve Yacht Parties

-Annapolis & Baltimore-

December 31, 2023

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!