There’s no place quite like Annapolis during the holiday season, when twinkling lights reflect off the water and history feels especially alive. This year, Watermark is offering a lineup of tours and cruises that bring the charm, stories, and sparkle of the season to life. Whether you prefer strolling lantern-lit streets, stepping inside historic landmarks, or taking in the scenery from the water with a cup of cocoa in hand, these experiences offer something for every kind of holiday celebrator. Here’s a guide to everything Watermark has planned to make your December unforgettable.
Watermark’s Holiday Candlelight Stroll
Fridays and Saturdays through December, departing at 7 PM from Watermark’s office at 188 Main Street (no tour Saturday, December 13)
Welcome the holidays with an evening tour of Annapolis. Led by lantern, your period-attired guide will escort you through 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’ll take home a goody bag of treats, including George Washington’s famed eggnog recipe! Adults $28; Children $15.
Watermark’s Special Historic Holiday Tour
Saturdays and Sundays through December, departing at 3 PM from Watermark’s office at 188 Main Street
Follow your period-attired guide through the charming streets of Historic Annapolis, beautifully adorned in greenery for the season. Warm up inside the Maryland State House (ID required for adults) and admire the uniquely decorated Federated Garden Clubs of Maryland Christmas trees, each representing a different Maryland county plus Baltimore City. The tour concludes at the city’s Christmas tree at Market House Park, followed by a festive goody bag to take home, including George Washington’s famed eggnog recipe! Adults $30; Children $16.
Watermark’s Jolly Express Cruises
Thursday–Sunday through December, plus 12/22, 12/23, 12/24, and 12/31, departing from the piers at 1 Prince George Street, Annapolis
Annapolis’ favorite holiday activity returns for the 2025 season. Miss Anne will be decked out in reindeer spirit for an intimate 45-minute “sleigh ride” along Spa Creek. Captain Santa or Mrs. Claus will be at the helm while an onboard elf serves hot cocoa and good cheer. Blankets will be available to keep you warm and cozy. It’s a perfect way to start a family holiday tradition. In the spirit of giving, a portion of proceeds is donated to Historic Annapolis. Ticket includes the cruise and your first cup of cocoa. Adults $28; Children $15.
Watermark’s Lights Parade Dinner Cruise
Saturday, December 13, 5-8 PM
Join Watermark and Ken’s Creative Kitchen aboard Catherine Marie for an intimate holiday dinner. Live jazz and holiday classics by Fred Hughes and Steve Meashey set the mood for appetizers and dinner on the main deck. Then head to the open-air top deck to take in the scenery and enjoy the Eastport Yacht Club’s Lights Parade. Tickets include an open beer and wine bar, butler-served hors d’oeuvres, and a full dinner and dessert service at a private table. $235 per person.
Watermark’s Queen of All Fund Drives
Saturday, December 13, 5-8 PM at the piers of 1 Prince George Street
Join Watermark and The Eastport Yacht Club Foundation for the Queen of All Fund Drives. Climb aboard Harbor Queen—fully decked out and aglow for the holidays—to enjoy festive music, beverages from the full-service cash bar, and a front-row seat for the Lights Parade. Instead of a ticket, the EYC Foundation will collect donations of $10 or more per person.
Annapolis Family-Friendly New Year’s Eve Cruise
Departing at 8 PM from the piers at 1 Prince George Street, Annapolis
Make your New Year’s Eve one to remember with this special family-friendly celebration on the water. Cruise aboard a Watermark yacht and dance to DJ Lampdawg’s tunes. Adults enjoy a complimentary glass of bubbly and kids receive a cup of cocoa, plus everyone gets a front-row seat for Annapolis’ fireworks display. Celebrate the end of 2025 on board, then head into town—or home—to ring in the new year. Alcoholic and non-alcoholic drinks will be available for purchase from the full-service bar. The City of Annapolis has scheduled fireworks for 9:00pm. $109 per adult; $59 for children under 13.
With lanterns glowing, music drifting across the water, and Annapolis dressed in its festive best, Watermark’s holiday tours and cruises capture the magic of the season from every angle. Whether you’re starting a new family tradition, entertaining out-of-town guests, or simply carving out a moment to savor the beauty of winter in Maryland’s capital city, these experiences offer a joyful way to celebrate. Bundle up, bring someone you love, and let Watermark help you make warm memories on even the chilliest days of the year.
Homestead for the Holidays