holiday-events-2023

Holiday Experiences

Annapolis & Baltimore - 2023

Holiday Cruises

Jolly Express Cruise

Annapolis’ favorite holiday activity makes its return for the 2023 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. Captain Santa is at the helm during this festive evening cruise on Spa Creek. Blankets will be available to stay warm and cozy. This is the perfect opportunity to start a family holiday tradition. In the spirit of the season, a portion of proceeds will be donated to Historic Annapolis.

Book Now

New Year’s Eve Annapolis Yacht Party

Make your New Year’s Eve memorable with this special celebration on the wate. Ring in the New Year on an exclusive and fun cruise aboard a luxury yacht with a DJ, dancing, desserts, a complimentary glass of bubbly, and fireworks!

Book Now


Holiday Walking Tours

Holiday Candlelight Stroll

Welcome the holidays with an evening walking tour of Annapolis. Your period-attired guide will lead you by lantern as you stroll around Maryland’s state capital, trimmed in greenery. Hear holiday traditions of times past as you walk by colonial mansions, Victorian homes, and quaint shops. Bring home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe!

Book Now

Special Historic Holiday Tour with the Hammond-Harwood House

Welcome the holidays with a walking tour of Annapolis. Stroll through Maryland’s state capital, trimmed in greenery, with your period-attired guide. Hear holiday traditions of times past as you walk by colonial mansions, Victorian homes, and quaint shops. The Hammond-Harwood House is the final stop on your tour. There, enjoy authentic, colonial, holiday decorations provided by local garden clubs, and learn about early nineteenth-century holiday traditions.

Book Now

Jolly Express photo by Adam Brockett.