The Magic of Christmas in Lynchburg, Williamsburg, Norfolk and Portsmouth

Experience the magic of the holiday season on this festive journey through Lynchburg, Williamsburg, Norfolk, and Portsmouth. From historic holiday traditions and dazzling light displays to charming waterfront celebrations and seasonal entertainment, this itinerary showcases the warmth, history, and spirit of Christmas across some of Virginia's most beloved destinations. 

Day 1: Lynchburg (Wednesday)

Afternoon Arrival in Lynchburg

Step back in time at Point of Honor, the picturesque 1815 Federal-style home overlooking the James River, where costumed interpreters and period holiday decorations bring Lynchburg’s early 19th-century history to life. It’s the perfect festive stop to experience traditional Virginian seasonal heritage and timeless charm. (1.5 hours)

Enjoy dinner at Depot Grille, a charming restaurant housed in Lynchburg's restored historic train station along the riverfront. 

Stroll along downtown's bluffwalk during Bright Nights, where thousands of twinkling holiday lights and festive decorations transform the pedestrian pathway into a magical winter wonderland. Complete with scenic views of the James River and sparkling photo opportunities, it’s an enchanting seasonal highlight for all ages. (1 hour)

Overnight Lynchburg 

Day 2: Lynchburg, Charlottesville and Williamsburg (Thursday)

Experience the festive local spirit at the Lynchburg Community Market, one of the oldest open-air markets in the country, brimming with seasonal baked goods, fresh regional produce, and handcrafted artisan gifts. It's an inviting holiday stop to pick up unique local treasures while soaking in the warm community atmosphere. (1.5 hours)

Discover the rich tapestry of the Hill City's past at the Lynchburg Museum, housed inside the landmark 1855 Old Court House overlooking downtown. (1 hour)

Depart for Williamsburg stop in Charlottesville

Savor traditional hearty Southern fare and browse unique artisan gifts inside quaint, historic merchant shops decked out for the season at Michie Tavern.

Experience the timeless grandeur of Thomas Jefferson’s iconic hilltop estate, Monticello, beautifully framed by winter vistas of the surrounding Virginia countryside. Seasonal guided tours offer an insightful look into historic holiday traditions and the complex history of this UNESCO World Heritage Site. (2 hours)

Depart for Williamsburg

Arrive in Williamsburg, the heart of Virginia’s Historic Triangle, and settle into your hotel. With a unique blend of American history, holiday traditions, exciting attractions, and group-friendly experiences, Williamsburg is the perfect destination for a memorable winter getaway. 

Enjoy a delicious group dinner at one of Williamsburg’s welcoming restaurants before choosing from one of the many exciting evening experiences as  Busch Gardens’ Christmas Town (2 hours) where the park comes alive with millions of twinkling lights, festive entertainment, seasonal attractions, and holiday cheer or a enjoy an evening of incredible magic, laughter, and audience participation at The Wagster’s Magic Theater (90 minutes)

Overnight Williamsburg

Day 3: Williamsburg & Jamestown (Friday)

Historic Jamestowne
Explore the site of America’s first permanent English settlement, where archaeological discoveries bring Jamestown’s fascinating history to life. (1 hour)

Jamestown Settlement
Experience history through immersive exhibits and living-history experiences, including a recreated Powhatan village, replica ships, and a 1610–14 fort. (2 hours)

Take a break for lunch at Jamestown Café, conveniently located at Jamestown Settlement. 

Enjoy some free time for shopping at Williamsburg Premium Outlets, featuring a variety of popular brands and outlet stores. (2 hours)

Group dinner

Enjoy a memorable group dinner surrounded by the charm and history of Williamsburg’s Historic Area. 

Ghost Tour or Evening Program in Colonial Williamsburg

As evening falls, discover another side of Williamsburg with a ghost tour or evening program in Colonial Williamsburg. (1 hour)

Day 4: Williamsburg (Saturday)

Colonial Williamsburg & Grand Illumination (Occurs on the first three Saturdays in December, unless otherwise noted)

Colonial Williamsburg
Spend the morning touring Colonial Williamsburg dressed in festive holiday decorations, with seasonal programming, traditions, and historic interpreters throughout the Historic Area. (3 hours)

Lunch in Merchant Square
Enjoy lunch at a group-friendly restaurant or choose from the many dining options in Merchant Square.

Williamsburg Christmas Market
Browse festive vendors, unique gifts, seasonal treats, and handcrafted items at the Williamsburg Christmas Market. (1 hour)

Return to the hotel to relax, refresh, and prepare for the evening festivities.

Enjoy an early dinner in the Historic Area, Merchant Square, or at a nearby group-friendly restaurant.

Grand Illumination
Celebrate Williamsburg’s holiday tradition with festive decorations, live music throughout the Historic Area, and spectacular fireworks lighting up the sky from the Capitol and Governor’s Palace. (2 hours)

Day 5: Yorktown, Portsmouth & Norfolk (Sunday)

Hotel check out

Enjoy a morning exploring historic Yorktown and the American Revolution Museum at Yorktown, where immersive exhibits and living-history experiences bring the story of the American Revolution to life. (1 hour)

Depart for Portsmouth

Portsmouth & Norfolk Holiday Finale

Visit Portsmouth Art & Cultural Center. Enjoy the Winter Wonderland exhibit and indoor holiday displays

Lunch & Movie

Visit the Commodore Theatre. Enjoy classic movie palace atmosphere, lunch served during the film

In the afternoon, take a Holiday Walking Tour. Explore the Olde Towne Historic District

Cozy Coastal Holiday  in Norfolk - Take a guided tour of historic St. Paul’s Episcopal Church, one  of Norfolk’s oldest landmarks, to admire Gothic architecture, intricate stained glass, and centuries of rich heritage.

Gather for a memorable group dinner at Omar's Carriage House, one of Norfolk's most beloved locally owned restaurants. Housed in a beautifully restored 19th-century carriage house dating back to the 1840s, the historic building once served as the carriage house for a grand downtown residence before being transformed into the charming restaurant it is today. 

Winterfest on the Wisconsin, the holiday celebration that earned national recognition on ABC’s The Great Christmas Light Fight in 2025 aboard Battleship Wisconsin. Stroll the historic decks transformed by more than two million lights, step inside the immersive exhibits, experience below deck, explore the festive Winterfest Riverwalk, enjoy seasonal entertainment, and take in sweeping waterfront views throughout the evening. 

Cap off the day with a 30-minute Victory Rover Naval Base Cruise, taking in holiday lights and festive waterfront views along Norfolk’s harbor. 

Day 6: Depart (Monday)

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