We Rank The 4 Best Christmas Experiences & Tours In Williamsburg

Discover the top Christmas experiences in Williamsburg, from private decorated walks to historical holiday tours and WWII character reenactments, perfect for making your holiday memorable.

Williamsburg transforms into a holiday wonderland during Christmas, with its beautifully preserved historic streets and buildings dressed in festive decorations. Unlike generic holiday destinations, Williamsburg offers a deep dive into colonial Christmas traditions and immersive experiences that bring history and holiday cheer together. You won’t find tacky light displays here; instead, expect authentic wreaths, historical stories, and guided tours that reveal how Christmas was celebrated centuries ago. This makes Williamsburg an ideal spot for history lovers, families, or anyone looking to celebrate the season with meaningful, educational festivities.

During the holiday season, the town’s historic architecture and carefully curated decorations provide a charming backdrop that feels both festive and authentic. Whether you’re strolling along Duke of Gloucester Street or learning about Christmas on the homefront during World War II, each tour offers a unique way to experience Williamsburg during the holidays. To help you choose, we’ve compiled a list of the best Christmas experiences and tours in Williamsburg, from private decorated walks to lively reenactments.

1. Private Colonial Williamsburg Christmas Holiday Decorations Walking Tour

Private Colonial Williamsburg Christmas Holiday Decorations Walking Tour

This exclusive, private tour is perfect for those who want an intimate exploration of Williamsburg’s holiday decorations. For $125 per person, you get about 1.5 hours of personalized insight into the materials, craftsmanship, and judging criteria used in colonial wreaths and garlands. The tour starts at the Williamsburg Inn, where parking is included, and then heads to the Duke of Gloucester Street, giving you a close-up look at the picturesque holiday displays.

What makes this tour stand out is the focus on understanding 18th-century decorating techniques—from how the wreaths are made to what categories the decorations are judged on. Led by a knowledgeable guide, you’ll learn about the craftspeople behind these decorations and the history behind their design. The guide also points out how private homes and public buildings participate differently, adding layers to your holiday understanding. Guests consistently praise the personalized experience, with reviews calling it “perfect because it was at our pace” and “very thorough and interesting.” Priced at $125, it offers a more exclusive, leisurely experience especially suited for history enthusiasts who want a deeper appreciation of colonial holiday traditions.

Bottom Line: For those wanting a private, detailed look at colonial holiday decorations with expert insights, this tour delivers a personalized and immersive experience that goes beyond just looking at pretty lights.

2. Guided Colonial Christmas Tour in Williamsburg

Guided Colonial Christmas Tour in Williamsburg

At around $25 per person, the Guided Colonial Christmas Tour offers a lively, well-rounded look at Williamsburg’s Yuletide traditions through the lens of history and storytelling. It lasts about 1.5 hours and features a costumed guide who shares stories about holiday customs, decorations, and colonial life during Christmas.

What makes this tour special is the authentic costume and the personal candles given to each participant, which add a cozy, festive feel. The tour covers highlights such as the Bruton Parish Episcopal Church, the Capitol Building, and various historic homes decorated for the season. The guide offers stories about how colonists celebrated Christmas and the significance of certain traditions, including pirate festivities. Many reviewers mention how engaging and informative the guide was, with comments like “Tom was an excellent guide—entertaining and knowledgeable.” This tour fits travelers interested in a broad overview of colonial Christmas customs without a hefty price tag, making it ideal for families or casual history buffs.

Bottom Line: If you want a fun, engaging, and affordable way to learn about colonial Christmas traditions with a lively guide, this tour hits the mark. It’s perfect for those interested in holiday stories and historic sites.

3. Christmas on the Homefront: A 1-Hour World War II Character Tour

Christmas on the Homefront: A 1-Hour World War II Character Tour

Stepping into a different kind of holiday history, this Christmas on the Homefront takes you back to Williamsburg in 1943. For $25, the 1-hour tour immerses you in wartime Christmas celebrations, with guides playing roles such as USO hostesses or Air Raid Wardens, giving a lively, theatrical touch.

What makes this tour unique is its focus on the wartime experience, including rationing, blackout drills, and the presence of military personnel. You’ll visit sites like Bruton Parish Episcopal Church and the George Wythe House, where guides discuss homes housing troops, wartime hardships, and the contributions of the African American community. The tour offers a vivid picture of how Christmas was celebrated amidst the challenges of war, emphasizing community resilience and wartime sacrifices. The reviews highlight the attention to historical accuracy and the engaging participation, with one remarking it as “a great way to experience history actively.” This tour is ideal for history buffs who want a dynamic, story-driven experience emphasizing American wartime holiday traditions.

Bottom Line: For travelers interested in a less typical holiday experience that combines history, reenactment, and wartime stories, this tour delivers an engaging hour of educational fun.

4. Tales of Christmas Past and Present in Williamsburg

Tales of Christmas Past and Present in Williamsburg

Finally, for those curious about how Christmas traditions evolved from colonial times to today, Tales of Christmas Past and Present offers a 1-hour walking tour through Williamsburg’s historic streets. Priced at $25, the tour covers the history behind modern decorations and how colonial Christmas celebrations influenced current practices.

Your guide will explore the role of the Bruton Parish Episcopal Church, the history of the George Wythe House, and the first recorded Christmas tree in Virginia at the Tucker House. The tour also discusses how decorations, festivities, and social norms have shifted over centuries. While reviews are not available, the focus on evolution of holiday customs makes this a fascinating choice for those interested in the broader story of Christmas traditions. It does not include entry to historic buildings but emphasizes storytelling and historical context.

Bottom Line: Ideal for travelers curious about the origins and transformation of Christmas customs, this tour offers a broad perspective on holiday traditions in Williamsburg.

How to Choose the Right Williamsburg Christmas Tour

When selecting a Christmas tour in Williamsburg, consider your interests and the kind of experience you’re after. If you prefer a private, detailed look at colonial decorations, the Private Colonial Williamsburg Christmas Holiday Decorations Walking Tour is ideal, especially for those wanting a leisurely, personalized experience. For a more affordable, storytelling-focused experience, the Guided Colonial Christmas Tour offers a lively overview suitable for families or casual visitors.

Travelers interested in wartime history and an active, theatrical approach should consider the Christmas on the Homefront, while those fascinated by historical evolution and how Christmas customs developed will find the Tales of Christmas Past and Present compelling.

Book early, especially for popular tours, and consider how much time you want to dedicate. Many of these experiences run for about 1 to 1.5 hours, making them easy to fit into a busy holiday schedule.

Williamsburg offers a variety of Christmas experiences that blend history and holiday cheer in a way that’s both educational and festive. Whether you opt for a private wreath decorating tour, a lively storytelling walk, or a wartime reenactment, you’ll find that celebrating Christmas in Williamsburg is about connecting with the past in a meaningful way. For a truly memorable holiday, consider booking your preferred tour early — these experiences tend to fill up quickly as the season approaches.