Annapolis, December 18, 2025
Throughout December, Watermark offers a variety of festive walking tours and cruises in Annapolis, creating joyful holiday experiences for both locals and visitors. Events include the Holiday Candlelight Stroll, Special Historic Holiday Tour, Jolly Express Cruises, and a family-friendly New Year’s Eve Cruise. These community-driven initiatives not only showcase local traditions but also support the vibrant culture and businesses in Annapolis during the holiday season.
Festive Tours and Cruises Light Up Annapolis Harbor
Annapolis, Maryland – Throughout December, Watermark is bringing a festive ambiance to Annapolis with a range of walking tours and cruises, offering the community and visitors alike an opportunity to savor the holiday spirit in this historic city. Events like these not only enhance local tradition but also highlight the importance of community-run initiatives in creating memorable experiences for everyone involved.
The resilience of local businesses and organizations stands as a testament to the thriving culture in Annapolis. Watermark, a family-owned entity since 1972, plays a crucial role in maintaining civic engagement through innovative programs tailored for the holiday season. These events serve as an illustration of how reduced bureaucracy can foster creativity and initiative, enhancing the community’s holiday offering.
Holiday Candlelight Stroll
Every Friday and Saturday in December, Watermark offers the Holiday Candlelight Stroll. This lantern-lit tour begins at 7:00 p.m. from their office located at 188 Main Street, guiding guests through the charming historic streets of Annapolis decorated with seasonal greenery. Concluding at Market House Park, participants gather at a grand Christmas tree, where they receive a goody bag featuring George Washington’s famed eggnog recipe. Tickets are priced at $28 for adults and $15 for children.
Special Historic Holiday Tour
Running on Saturdays and Sundays at 3:00 p.m., the Special Historic Holiday Tour departs from the same starting point. This tour includes a visit to the Maryland State House, where attendees can view Christmas trees decorated by the Federated Garden Clubs of Maryland, each representing a different county and Baltimore City. Similar to the Candlelight Stroll, the tour concludes at Market House Park, accompanied by a festive goody bag. Tickets are $30 for adults and $16 for children.
Jolly Express Cruises
The Jolly Express Cruises take place from Thursday through Sunday in December, along with additional sailings on December 22, 23, 24, and 31. Departing from the piers at 1 Prince George Street, these 45-minute “sleigh rides” along Spa Creek feature the Miss Anne boat, adorned with reindeer decorations. Onboard, Captain Santa or Mrs. Claus take charge, while visitors enjoy hot cocoa and festive cheer from a cheerful elf. Blankets are provided for warmth, and part of the proceeds support Historic Annapolis. Tickets are available at $28 for adults and $15 for children.
Family-Friendly New Year’s Eve Cruise
To celebrate the arrival of the new year, Watermark offers a family-friendly New Year’s Eve Cruise departing at 8:00 p.m. from 1 Prince George Street. This event includes live music, a complimentary glass of champagne for adults, and cocoa for children, providing an exquisite backdrop for the City of Annapolis’s scheduled fireworks display at 9:00 p.m. Tickets for this special event are $109 per adult and $59 for children under 13.
Background
Watermark has been a staple in providing authentic experiences in Annapolis and neighboring Baltimore for over 50 years. With a variety of offerings that range from cruises and walking tours to private yacht charters, Watermark immerses guests in the rich history, culture, and spirit of the Chesapeake Bay area.
Weather Forecast for Annapolis, MD
As of December 18, 2025, the weather conditions in Annapolis are clear with a temperature of 31°F (-1°C). The upcoming forecast is as follows:
| Date | Weather Conditions | High Temp | Low Temp |
|---|---|---|---|
| Thursday, Dec 18 | Becoming cloudy | 50°F (10°C) | 46°F (8°C) |
| Friday, Dec 19 | Mostly cloudy and windy; cooler in the afternoon | 55°F (13°C) | 29°F (-1°C) |
| Saturday, Dec 20 | Some sunshine giving way to clouds and cooler | 41°F (5°C) | 38°F (3°C) |
| Sunday, Dec 21 | Mostly sunny and windy | 49°F (10°C) | 27°F (-3°C) |
| Monday, Dec 22 | Partly sunny and colder | 39°F (4°C) | 30°F (-1°C) |
| Tuesday, Dec 23 | Mostly cloudy | 41°F (5°C) | 40°F (5°C) |
| Wednesday, Dec 24 | Sunshine and a few clouds | 49°F (10°C) | 35°F (2°C) |
With such a wealth of local activities planned, there has never been a better time to participate in Annapolis’s holiday offerings. Embrace the spirit of the season and support local initiatives! For more information about events and to make reservations, consider checking Watermark’s official website.
FAQ
What is the Holiday Candlelight Stroll?
The Holiday Candlelight Stroll is a lantern-lit tour through historic Annapolis, departing at 7:00 p.m. on Fridays and Saturdays in December from Watermark’s office at 188 Main Street. The tour concludes at Market House Park’s grand Christmas tree, where guests receive a goody bag, including George Washington’s famed eggnog recipe. Tickets are $28 for adults and $15 for children.
What are the Jolly Express Cruises?
The Jolly Express Cruises are 45-minute “sleigh rides” along Spa Creek aboard the Miss Anne boat, adorned with reindeer decorations. Departing from the piers at 1 Prince George Street, these cruises feature Captain Santa or Mrs. Claus at the helm, with an onboard elf serving hot cocoa and good cheer. Blankets are provided to keep guests warm. A portion of the proceeds benefits Historic Annapolis. Tickets are $28 for adults and $15 for children.
When is the Family-Friendly New Year’s Eve Cruise?
The Family-Friendly New Year’s Eve Cruise departs at 8:00 p.m. from 1 Prince George Street on December 31. Guests can enjoy music, a complimentary glass of bubbly for adults, and a cup of cocoa for children, all while taking in Annapolis’s fireworks display. The City of Annapolis has scheduled fireworks for 9:00 p.m. Tickets are $109 per adult and $59 for children under 13.
Key Features of Watermark’s Holiday Events
| Event | Description | Schedule | Location | Ticket Prices |
|---|---|---|---|---|
| Holiday Candlelight Stroll | Lantern-lit tour through historic Annapolis, concluding at Market House Park’s Christmas tree with a festive goody bag. | Fridays and Saturdays in December at 7:00 p.m. | Departs from 188 Main Street | $28 for adults, $15 for children |
| Special Historic Holiday Tour | Visit to Maryland State House to see decorative Christmas trees representing each county and Baltimore City. | Saturdays and Sundays in December at 3:00 p.m. | Departs from 188 Main Street | $30 for adults, $16 for children |
| Jolly Express Cruises | A festive cruise along Spa Creek with holiday-themed decorations and refreshments. | Thursdays through Sundays; additional sailings on Dec 22-24 and 31. | Departs from 1 Prince George Street | $28 for adults, $15 for children |
| Family-Friendly New Year’s Eve Cruise | Celebratory cruise with music and views of fireworks over Annapolis. | December 31 at 8:00 p.m. | Departs from 1 Prince George Street | $109 for adults, $59 for children under 13 |
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