(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 28th. Tickets are $28/adult and $15/child. Click here for reservations.
Hear the stories from our Holiday Candlelight Stroll. This festive tour takes place Saturdays and Sundays from 3:00pm to 4:45pm beginning November 29 and running through December 28. Tickets are $30 for adults and $16 for children 11 and under. Click here for reservations.
Annapolis’ ever-popular Jolly Express Cruise makes its return for the 2025 holiday season. Miss Anne will be adorned with holiday lights and reindeer spirit for an intimate 45-minute “sleigh ride” including hot cocoa, holiday music, and good cheer. Captain Santa or Mrs. Claus will be at the helm for this festive evening cruise on Spa Creek. We even have cozy blanket to keep you warm. This is the perfect opportunity to start a family holiday tradition. In the spirit of the season, Watermark donates a portion of proceeds to Historic Annapolis. Jolly Express begins cruising Saturday, November 22 and runs weekends plus Black Friday, then Thursday-Sunday through December 28 – plus December 23, 24, 31 and January 1. Tickets are $28 for adults and $15 for children 11 and under. 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. Dance to the rhythms of DJ [ask Linda], enjoy a complimentary glass of bubbly, and a view of the city’s 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.
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.