Watermark’s end-of-year holiday cruises and tours of Annapolis

Watermark’s Holiday Candlelight Stroll
Fridays and Saturdays through December, departing at 7:00pm from Watermark's office at 188 Main Street (no tour Saturday, December 13)
Welcome the holidays with an evening tour of Annapolis. Lead by lantern, your period-attired guide will lead you around Maryland’s capital city, trimmed in greenery for the season. Hear holiday traditions of times past and present as you walk by colonial mansions, Victorian homes, and quaint shops. End the tour at the grand Christmas tree at Market House Park where you can bring home the holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe! Adults $28; Children $15. www.watermarkjourney.com
 
Watermark’s Special Historic Holiday Tour
Saturdays and Sundays through December, departing at 3:00pm from Watermark's office at 188 Main Street
Follow your period-attired guide through the streets of Historic Annapolis, adorned in greenery for the season. Warm up with a stop at the Maryland State House (ID required for adults), where you will enjoy the uniquely decorated Federated Garden Clubs of Maryland Christmas trees. Each tree represents a different Maryland county as well as Baltimore City. End at the city's Christmas tree at Market House Park. After the tour, take home some holiday cheer with a goody bag of treats including George Washington’s famed eggnog recipe! Adults $30; Children $16. www.watermarkjourney.com
 
Watermark’s Jolly Express Cruises
Thursday-Sunday through December, plus 12/22, 12/23, 12/24, & 12/31, departing from the Piers at 1 Prince George Street, Annapolis
Annapolis' favorite holiday activity makes its return for the 2025 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute "sleigh ride" along Spa Creek. Captain Santa or Mrs. Claus will be at the helm, and an elf will be on board serving hot cocoa and good cheer. 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 are donated to Historic Annapolis. Ticket includes the cruise and your first cup of hot cocoa. Adults $28; Children $15. www.watermarkjourney.com
 
Watermark’s Lights Parade Dinner Cruise
Saturday, December 13, 5:00-8:00pm
Join Watermark and Ken’s Creative Kitchen aboard Catherine Marie for an intimate holiday dinner. Live jazz and holiday classics with Fred Hughes and Steve Meashey set the mood for appetizers and dinner on the 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. $235 per person. www.watermarkjourney.com or call our sales office at 410-268-7601).
 
Watermark’s Queen of All Fund Drives
Saturday, December 13, 5:00-8:00ppm at the Piers of 1 Prince George Street
Join Watermark and The Eastport Yacht Club Foundation Saturday, December 13th, from 5:00pm to 8:00pm for the Queen of All Fund Drives. Climb aboard Harbor Queen all decked out and aglow for the holidays to enjoy festive music, beverages from our full-service cash bar, and a front-row seat to the Lights Parade. In lieu of a ticket, The EYC Foundation will be collecting donations of $10 or more per person. www.watermarkjourney.com           
 
Annapolis Family-Friendly New Year's Eve Cruise
Departing at 8:00pm from the Piers at 1 Prince George Street, Annapolis
Make your New Year’s Eve memorable with this special family-friendly celebration on the water in Annapolis. Cruise aboard a Watermark yacht and dance to DJ Lampdawg’s tunes; Enjoy a complimentary glass of bubbly for the adults and a cup of cocoa for the kids, and a front-row seat of Annapolis’s fireworks display. Celebrate the end of 2025, and then head into town (or to your couch) to ring in the new year. Alcoholic and non-alcoholic beverages will be available for purchase from our full-service bar. The City of Annapolis has scheduled fireworks for 9:00pm. $109 per adult; $59 for children under 13. www.watermarkjourney.com