Holiday Experiences

Annapolis & Baltimore - 2023

Queen of All Fund Drives

 Join us aboard Harbor Queen all decked out for the holidays to enjoy festive music, a beverage from our cash bar, and a front-row seat to the 2023 Lights Parade. Your ticket in is a suggested monetary donation of $10 or more per person to benefit We Care and Friends. They will also be accepting donations of toys, linens, bedding, blankets, toiletries, clothing, and non-perishable food items. This incredible organization “is dedicated to supporting the building blocks to create strong families and communities in areas affected by drugs, poverty, and crime in Maryland.” Come on down and celebrate the season of giving with Watermark!

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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.

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Holiday Dinner Cruise with Ken’s Creative Kitchen

Join Watermark and Ken’s Creative Kitchen aboard Raven for an intimate holiday dinner. Enjoy music and dinner on the enclosed main deck. Then, venture to the open-air top deck to take in the scenery and see the Eastport Yacht Club’s Lights Parade. Included in the ticket are an open beer and wine bar, butler-served hors d’oeuvres, as well as dinner and dessert service at a private table.

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New Year’s Eve Yacht Parties

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!

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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!

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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.

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Jolly Express photo by Adam Brockett.

2023 Holiday Happenings
November & December
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