Experience
Discover Annapolis Waterfront Hotel
Each season leaves its mark on the harbor. In winter, the lights multiply, the air sharpens, and familiar traditions return to the calendar. From races across the Bay to boats lit for the holidays, Annapolis feels both storied and alive. Here’s what’s waiting nearby.
Midnight Madness
December 4th, 11th, & 18th
On a trio of December evenings, downtown Annapolis comes alive after dark. Stroll brick-lined streets beneath glowing garlands and canopies of snowflakes. Sip something warm, browse locally owned shops, and enjoy free street performances that feel straight out of a storybook. The first two Thursdays run until midnight, with the final night wrapping up at 11 PM—a festive tradition that lights up the whole city.
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.
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.
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.
Annapolis Holiday Market
December 2025 – Dates TBA
Framing the historic waterfront, the Annapolis Holiday Market brings together more than 100 regional artisans and food vendors. From Chesapeake-made crafts to hot cider in mittened hands, it’s a chance to experience the city at its most festive.
Eastport Yacht Club Lights Parade
December 13th
Every December, a fleet of boats trimmed in lights sails across the Annapolis Harbor, a decades-old tradition known as the Eastport Yacht Club Lights Parade. It's Annapolis at its most magical, blending maritime pride with holiday spirit. Watch from the Spa Creek Bridge, catch glimpses from a pocket park, or enjoy the view with a warm drink from our dockside perch
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. 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.
Candlelight Concerts
This December, experience the magic of live music under the glow of candlelight at Annapolis Waterfront Hotel.
December 14, 6:30 PM – Candlelight: Coldplay & Imagine Dragons — A stunning tribute featuring the biggest hits from two iconic bands, reimagined by a string quartet.
December 21, 6:30 PM & 8:30 PM – Candlelight: Christmas Carols on Strings — Celebrate the season with timeless holiday favorites performed in a warm, candlelit setting.
Tickets from $51.
Military Bowl
December 27th
College football finds a home in Annapolis each winter, as teams from the ACC and AAC face off at the Navy–Marine Corps Memorial Stadium. The Military Bowl turns the city into a stage for parades, pageantry, and pride, all in support of veterans and their families. Kickoff may be at 11 AM, but the energy lasts all day.
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.