Download the full itinerary to get more information on dining, lodging and side trips.
Two Days / One Night
Get into the holiday spirit with a tour of St. Mary’s County featuring holiday lights, small town charm, and colonial traditions!
First Stop: St. Mary’s County Welcome Center. Freshen up at our Welcome Center housed in a historic building that was once part of the Charlotte Hall Military Academy.
Second Stop: Cecil’s Country Store and Cecil’s Old Mill. Shop for unique Christmas gifts at the turn-of-the-century country store and adjacent old mill. Find antiques, collectibles, and artwork by local artists.
Third Stop: Holiday Lunch at Historic St. Mary’s City. Step back in time to the 17th-century at Historic St. Mary’s City, Maryland’s first colony and first capital! Enjoy lunch near the State House of 1676 decorated for the holidays. Then, tour Historic St. Mary’s City and experience what life was like in colonial Maryland through living history exhibits.
Fourth Stop: Dinner. Enjoy dinner at a lovely group-friendly restaurant.
Fifth Stop: Christmas Light Display at Flat Iron Farm. See the beautiful Christmas light display at Flat Iron Farm! The theme of the light display changes each year. The farm also features Christmas shops and goodies.
Overnight: Stay at one of our finest group-friendly hotels and enjoy the special touches that make you know you are welcome! Enjoy a complimentary breakfast before beginning a second exciting day!
First Stop: Piney Point Museum Holiday Exhibit. Visit the Piney Point Lighthouse Museum for a holiday-themed exhibit! The exhibit’s theme changes each year and includes a tour of the lighthouse keeper’s quarters.
Second Stop: Shopping and Lunch in Historic Leonardtown. Enjoy lunch at one of the Town’s many great restaurants! Then, do some holiday shopping at unique specialty stores decorated for Christmas.
Third Stop: Port of Leonardtown Winery. Participate in a tour of the winery and then sample some of the local flavor during a wine tasting! All of the wines made at the Port of Leonardtown Winery include locally-grown grapes.
Fourth Stop: Tour at Sotterley Plantation. (Available only on certain days). Head over to Sotterley Plantation for a tour of the Manor House! Sotterley Plantation is a Tidewater Plantation that dates back to the 18th-century.
Fifth Stop: Dinner. Enjoy dinner at a lovely group-friendly restaurant.
Board bus for return trip.
Southern Maryland is also known for its fabulous festivals and events. Check out all of the holiday happenings on our Events page.