Celebrate the Holidays with Watermark

Holiday Cruises and Walking Tours

(Annapolis, MD) – Celebrate the holidays with Watermark®! We hope you’ll join us, and enjoy the charm, cheer, and spirit of Annapolis during the sparkly season. In addition to our holiday regulars, we are offering some new ways to enjoy the fresh air. “The holiday season in Annapolis is a magical time that we are always excited to share with our guests” said Jake Iversen, Watermark President. “Every year is a new opportunity to create lifelong memories and family traditions, and we are thrilled to be a part of that.”

Our traditional 90-minute Holiday Candlelight Stroll will lead you by lantern through the streets of Historic Annapolis. Stroll around Maryland’s historic State Capital trimmed in greenery, and walk with our period-attired guide, who will share holiday traditions of times past among 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! This event will take place Friday and Saturday evenings at 7:00pm beginning November 25th. Tickets are $25/adult and $14/child. Click here for reservations.

New this year is a Special Historic Holiday Tour with the Hammond Harwood House. Hear the stories from our Holiday Candlelight Stroll, and step into the Hammond-Harwood House as 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. Cider will be served, and the Hammond Square Gift Shop will be open for holiday shopping at the end of the tour. This event will take place Saturday, December 3rd, 10th, and 17th from 3:00pm to 4:45pm. Tickets are $28/adult and $15/child. Click here for reservations.

Annapolis’ favorite holiday activity makes its return for the 2022 holiday season. For our beloved Jolly Express Cruise, 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. Bring your own cozy blanket to keep you warm. 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. Beginning November 25th, this event will take place Friday and Saturday evenings from 4:00pm to 8:00pm on the hour and Sunday evenings from 4:00pm to 7:00pm on the hour. Tickets are $25/adult and $13/child. Click here for reservations.

Make your New Year’s Eve memorable with a special celebration on the water. In Annapolis, step aboard Watermark’s flagship yacht, Catherine Marie, for a New Year’s Eve Annapolis Fireworks Cruise. Enjoy dancing, desserts, a DJ, a complimentary glass of bubbly, and fireworks. This event takes place on Saturday, December 31st from 10:00pm to 1:00am. Tickets are $97/adult (21 and over only). Click here for reservations.

In Baltimore, Watermark is hosting a New Year’s Eve Charm City Cruise, with a DJ, dancing, desserts, a complimentary glass of bubbly to ring in the new year. Click here for more information and reservations.

Enjoy winter in the charming city of Annapolis, and celebrate the holidays with Watermark.


Click here for full press release.