Holiday travel is trending cozier this year. Deloitte’s 2025 Holiday Travel Survey shows that while more Americans plan to travel between Thanksgiving and mid-January, many are skipping big, complicated trips in favor of experiences that feel simple, close-to-home and genuinely festive.
Luckily for anyone in the Mid-Atlantic, few places deliver that kind of instant holiday magic like a waterfront at dusk. The twinkling lights reflecting on the water, the silhouette of boats gliding through the cold, and the shoreline glowing like its own strand of ornaments all make the Chesapeake Bay feel especially alive in December.
Yes, being on the water makes any season feel enchanted. And while the Chesapeake Bay in Maryland is hardly the only place to find that feeling, I’m admittedly partial as someone who lives in the state. These waters know how to show off in December. The state capital, Annapolis, transforms into a waterfront snow globe during the holidays, and Watermark, the region’s long-running cruise and tour operator, busts out the holly and garland to liven up its seasonal cruises and historic tours. And in other regions, local celebrations rooted in waterman culture delight attendees with their quintessentially Maryland flair.
Here are the most festive ways to get on (or near) the Bay this season.
Ways to get on the Chesapeake Bay over the holidays
Holiday Candlelight Stroll in Annapolis
From $28 for adults; $15 for children 11 and under
November through December
This 90-minute lantern-lit walking tour invites guests to take in the atmosphere of Annapolis during the holidays. A guide in period attire leads guests past colonial homes, Victorian residences and storefronts trimmed with greenery. The tour concludes at the Market House Christmas tree right along the waterfront, with guests taking home a small gift bag that includes George Washington’s historic eggnog recipe.
Christmas on the Creek in Oxford
Dec. 5, 2025 to Jan. 10, 2026
The waterfront town of Oxford, Md., launches its month-long “Christmas on the Creek” celebration on Dec. 5, which will transform docks along Town Creek with floating lit trees, festive music, markets and family-friendly activities. Highlights include a lighting ceremony aboard the Oxford-Bellevue Ferry, holiday markets on consecutive weekends and a display of decorated boatyards and waterfront sites. Visitors can stroll the shoreline, browse artisan booths and sip on seasonal refreshments local boatyards. Mark your calendars—the dock trees along Town Creek are scheduled to light up at sunset on Saturday, Dec. 6.
Special Historic Holiday Tour in Annapolis
$30 for adults; $16 for children 3 to 11
Saturdays in December
A daytime counterpart to the Candlelight Stroll, this extended tour begins with warm apple cider before guests join a lantern-led guide through the historic district. A highlight is a visit inside the Maryland State House, where the Federated Garden Clubs of Maryland decorate Christmas trees representing each county.
Watermark Lights Parade Dinner Cruise with Ken’s Creative Kitchen
(Watermark Journey)
Lights Parade Dinner Cruise in Annapolis
$235 per guest
Saturday, Dec. 13
This seasonal dinner cruise aboard the Catherine Marie livens up an otherwise dreary December Saturday with live jazz, passed hors d’oeuvres, a plated dinner and dessert before passengers move to the open-air deck to view the Eastport Yacht Club Lights Parade. (The annual boat parade is one of the region’s most recognizable holiday traditions. More on it below.)
Jolly Express Cruise in Annapolis, Md.
(Watermark Journey)
Jolly Express Cruise in Annapolis
$28 for adults; $15 for children 11 and under
November through December
A family favorite, this 45-minute cruise on Spa Creek is captained by Santa or Mrs. Claus and includes hot cocoa served by an onboard elf. Blankets are available for warmth, and private charters are offered for groups up to 21 passengers.
Queen of All Fund Drives in Annapolis
Suggested donation of $10 or more
Saturday, Dec. 13, 5 to 8 p.m.
If simply stepping aboard a boat is enough excitement for you and you like giving back more than cruising along the water, check out this dockside fundraiser. During the Eastport Yacht Club Lights Parade, Watermark hosts an open-house fundraiser aboard the Harbor Queen. Visitors will enjoy holiday music, a cash bar and views of the illuminated boats. Donations benefit the Eastport Yacht Club Foundation and its maritime-access programs for local youth.
Christmas Express Cruise at Baltimore’s Christmas Village in Baltimore
$28 for adults; $15 for children 11 and under
November through December
New this season, this 45-minute Inner Harbor cruise departs from the Christmas Village at Baltimore’s waterfront. You won’t technically be on the Chesapeake Bay, but rather the Patapsco River, which flows into it. Still, the boat is decorated for the holidays, and guests can enjoy cocoa and views of the European-style market from the water.
New Year’s Eve Annapolis Yacht Party
$109 for adults; $59 for children under 13
Wednesday, Dec. 31
A family-friendly cruise that includes music by DJ Lampdawg, dancing, a champagne toast for adults, hot cocoa for children and front-row views of Annapolis’s 9 p.m. fireworks.
Other ways to experience Maryland’s holiday cheer
Annapolis and Anne Arundel County sit right along the Chesapeake Bay, and their mix of historic streets, waterfront scenery and long-standing holiday traditions gives the region a distinctly cozy feel in December. So if you’re heading out on the water or want a few more ways to experience the season on land, there are plenty of local events that make it easy to tap into the area’s holiday spirit, even if it’s your first time visiting.
Midnight Madness
Dec. 4, 11 and 18
On just three nights, late-night holiday shopping is coming back to the city’s historic district. Downtown glows under twinkling lights, carolers wander the brick-lined streets and local shops stay open well past dark with specials, treats and surprises.
Shoppers can browse independent boutiques for one-of-a-kind gifts, warm up with complimentary s’mores at the Visitors Center and take in the annual gingerbread house display.
Crab basket Christmas Tree in Kent Narrows, Md.
(kentnarrowsmd.com)
Crab-Basket Tree Lighting in Kent Narrows
Dec. 6 (tree on display through early January)
Kent Narrows in Queen Anne’s County marks the season with its sixth annual crab-basket tree, a stacked tower of roughly 300 painted wooden bushel baskets near the Maryland Watermen’s Monument. A vendor fair opens at noon, and the tree is lit at 6 p.m. The event is free to attend, and the display remains up into January.
Annapolis Gingerbread Houses
(Visit Annapolis and Anne Arundel County)
Annapolis Gingerbread Houses
Through Dec. 19 (public voting through Dec. 7)
The annual gingerbread house contest at the Visitors Center brings in bakers, families and local groups who build everything from snow-covered cottages to candy-laden trains. Entries remain on view through Dec. 19, with public voting open until Dec. 7 and winners announced during the Annapolis Chocolate Binge Festival. Pop into this simple, sweet stop if you want a quick dose of holiday fun.
Eastport Yacht Club Lights Parade
Dec. 13
The Eastport Yacht Club Lights Parade returns to Annapolis Harbor and Spa Creek on Dec. 13. The event began in the 1980s as a small gathering of local boaters who decorated their vessels and sang carols on the water. It has since expanded into one of the city’s most recognizable holiday traditions, drawing thousands of spectators each year.
Viewers line the waterfront in downtown Annapolis and in Eastport, a residential peninsula across the Spa Creek Bridge known for its close connection to the boating community. From these spots, including small public parks and the bridge itself, spectators watch dozens of illuminated boats move slowly past. The parade is free to attend and remains a central part of the city’s holiday calendar.
Snowflake Alley in Annapolis, Md.
(Visit Annapolis and Anne Arundel County)
Snowflake Alley
All December
In a small passageway off Main Street in downtown Annapolis, a narrow pedestrian lane known locally as Cabbage Alley transforms into Snowflake Alley, a whimsical walkway strung with glowing, overhead snowflakes. It’s one of the city’s most photogenic holiday spots and a favorite for strolls, snapshots or anyone looking for a little seasonal atmosphere.
The surrounding streets get the same treatment. Main Street, West Street, Maryland Avenue, State Circle, Market Space and Dock Street are all lined with twinkling snowflake lights, turning Annapolis’s historic district into a full winter scene. Whether you’re shopping during Midnight Madness, browsing local boutiques or simply taking in the glow, these illuminated streets offer an easy, picture-perfect way to experience the city’s holiday charm.
Lights on the Bay at Sandy Point State Park, Md.
(Visit Annapolis and Anne Arundel County)
Lights on the Bay
Through Jan. 1
This annual two-mile drive-through holiday display at Sandy Point State Park runs nightly through Jan. 1. The route includes more than 70 light installations, ranging from traditional holiday scenes to larger, themed setups. The event is organized by the SPCA of Anne Arundel County, and proceeds support the organization’s animal welfare programs.
Some evenings include added programming, such as pet-focused walk-through periods, scavenger hunts and scheduled visits from Santa. The display has operated for decades and remains one of the region’s longest-running seasonal events along the Chesapeake Bay.
For visitors planning a holiday trip, or residents who want to see their hometown with fresh eyes, the season offers a mix of waterfront experiences and onshore traditions that together showcase the region’s winter charm.