Williamsburg Colonial Christmas

December 2-7, 2021 • 6 Days • $1990

This Yuletide Virginia vacation will bring to life some of America’s most significant historical eras with educational and engaging walks in Colonial Williamsburg, Jamestown, Yorktown, and the capital city of Richmond.

Attention non-walkers: Colonial Williamsburg provides a fun holiday experience for everyone, walkers and non-walkers alike! If you’d like to join us for the fun, but opt out of the walks, you can enjoy the endless holiday sights and sounds of the historic area while the walkers are out on the trail. In Richmond, you can explore the Civil War legacy of Capitol Square while the rest of us are walking. Just send us an email at [email protected] to let us know you are a non-walker.

Tour Complete

We explore this tapestry of timeless treasures all from the comfort of our hotel in Williamsburg, so you can unpack and unwind as we travel over 400 years back in time to the very roots of our nation’s story. In Jamestown, we stroll through America’s first permanent English settlement and enjoy a living history museum that not only focuses on the English settlers but also on the native Powhatan Indians (the people of Pocahontas). In Colonial Williamsburg, an amazing array of costumed interpreters and actors bring to life the tense scene shortly before we declared independence from Great Britain. With a featured walk, guided tour, and an entirely free day here, you’ll have ample opportunity to explore Williamsburg’s many living history museums and take advantage of excellent optional activities. In Yorktown, set foot on the historic battlefield where George Washington defeated Cornwallis and essentially won our independence. Finally, in Richmond, re-live some of the pivotal moments of the Civil War as we walk through the former capital of the Confederacy and the current capital of Virginia. This exciting 6-day adventure will leave you with wonderful memories and a renewed appreciation for our shared history as Americans!


  • Walks in Jamestown, Yorktown, Richmond, and Colonial Williamsburg
  • 5-night hotel stay near the heart of Colonial Williamsburg, with convenient, complimentary access to the town’s re-created 18th century atmosphere
  • Historic Jamestowne and Jamestown Settlement – England’s first permanent settlement in the New World
  • Yorktown Battleground and Victory Center – site of the final major clash of the American Revolution
  • Richmond – the heart of the Confederacy during the Civil War
  • Shirley Plantation – a visit to Virginia’s oldest plantation, established in 1613
  • One-of-a-kind dining experience at a Williamsburg historic tavern


  • All land travel as outlined
  • Superior tourist-class hotel accommodations: 5 nights in the same hotel near Colonial Williamsburg’s world-renowned historic area
  • All breakfasts as listed (B)
  • 4 AVA-sanctioned walks as listed
  • Fees for walking credit
  • All tipping for local guides and coach drivers
  • WAI guide service throughout
  • Pricing is based on double occupancy; a limited number of single rooms will be available for a supplement of $350. We will also provide a roommate matching service.

Activities/Entrance Fees:

  • Colonial Williamsburg
  • Jamestown Settlement
  • Historic Jamestown
  • Yorktown Battlefield
  • Yorktown Victory Center
  • Guided historical tour of Colonial Williamsburg Historic Area
  • Shirley Plantation tour
  • The Grand Illumination evening Christmas show
  • More fun stops than we can list!

Optional activities:

  • 18th century style dinner at one of Williamsburg’s historic taverns (Day 4 – December 5)
  • Several holiday programs and musical events available throughout the day and evening in Colonial Williamsburg
Colonial Williamsburg Map

Adventure Pace

Tour Pace: 1 2 3 4 5
Walk Challenge: 1 2 3 4 5

About Adventure Pace

Important Info

Your Guides

Scott IsomScott Isom has had a passion for the outdoors ever since his childhood days spent exploring the waterfalls and outstanding hiking trails of the Columbia River Gorge with his family. Scott has led tours on all 7 continents and is one of WAI’s busiest guides and on-site Adventure planners. Scott will be leading our Colonial Williamsburg Adventure along with a WAI Assistant.


This is a draft itinerary. Revisions will be made, and an updated itinerary with finalized dates and pricing will be made available!

Click on each day to reveal more details. BD refers to meals included, Breakfast and Dinner.

Travelers arrive from across the country today into Williamsburg/Newport News, a region known as America’s Historic Triangle. From the Williamsburg Airport (airport code PHF), we’ll provide information on how you can arrange your own transfer to our hotel in nearby Colonial Williamsburg, where we begin 6 days and 5 nights of Christmas celebrations that bring to life some of America’s most significant historical eras. Following a get-acquainted orientation this evening, feel free to explore the Yuletide sights and sounds of Williamsburg’s restored 18th century charms.

Jamestown Walk – 6 km, rated 1B

We start our morning by traveling over 400 years back in time to the very roots of our nation’s story. During a walk through America’s first permanent English settlement at Jamestown, a newfound appreciation develops for our 17th century forebearers. Following this first of many historic strolls, a short drive takes us to Jamestown Settlement, a living-history museum where our Colonial Christmas tour is enhanced by costumed interpreters. Enjoy the Settlement’s outdoor re-creations of a Powahatan Indian village, three ships modeled on the 1607 originals, and the colonists’ fort before returning to our hotel for the balance of the afternoon. This evening, feel free to get out and explore the historic holiday scenes in Colonial Williamsburg, where various optional activities await you.

Colonial Williamsburg Walk – 5 or 10 km, rated 1A

Today offers a wonderful opportunity to dive deeper into the Christmas delights, sights, and sounds of Colonial Williamsburg with its famous decorative doors awaiting our admiring stares. Our morning begins with a custom-made guided walking tour of the historic area, where our resident experts bring centuries-old stories to life in the heart of this important American town. After lunch on your own, the remainder of the day is devoted to choosing your very own holiday adventure.

What makes this evening even more special is the annual Grand Illumination, a Christmas celebration replete with fireworks, drum and fife performances, and multiple live musical and dance performances.  A helpful printed guide to optional programs will be provided to help you maximize your free time in our colonial home away from home.

Yorktown Battlefield Walk – 5 km, rated 2B

This morning, our motor coach transports us along the scenic Colonial Parkway on our way to Yorktown, site of the decisive and final battle of the Revolutionary War, where George Washington and our French allies forced the British to surrender. Envision this momentous event at the American Revolution Museum as we listen to historic accounts of Christmas and winter in the Revolutionary War encampments. We then retrace the footsteps of our first commander-in-chief on the Yorktown Battlefield during today’s walking event before we return to our hotel in the afternoon. The remainder of the evening is free for you to enjoy dinner and further explore our charming surroundings. During our stay in Williamsburg, we have unlimited entry to all daytime programs, museums, exhibition sites, and Revolutionary City. Within easy walking distance of our hotel, you will enjoy easy access to the historic center of town. For those interested in a nice dining experience in one of Colonial Williamburg’s historic taverns, reservations have been made at King’s Arm Tavern this evening

Richmond Capitol Walk – 10 km, rated 2B

A short drive north this morning takes us back to another crucial moment in American history as we walk in Richmond, current capital of Virginia and former capital of the Confederacy during the Civil War. While the city has changed a great deal in the last 150 years, many fine buildings and historical markers have survived and re-create for us a sense of this city’s important role in our national story. On our afternoon return trip to Williamsburg, we make a memorable stop at Shirley Plantation, one of the gracious country manor houses of the James River. Revel in a “Home for the Holidays” tour at this oldest of Virginia’s plantations, founded in 1613. We arrive back in Williamsburg’s historic environs for one last evening of holiday exploration!

Following breakfast at our hotel, you are free to arrange your transfer back to the Williamsburg/Newport News airport for your flights home. Full of historic holiday memories spanning several centuries, we return home to warmly celebrate our own traditions with family and friends.

More Details

Click on each heading for more details.

To register, a transferable $200 deposit is required to hold your spot. This amount is non-refundable; however, up until 60 days before departure, it can be transferred to a different tour.  A final payment is due 60 days before departure and you will receive a prompt email from us a week or two in advance.

An email with critical information on flight arrangements will be sent soon after registration, with important details about steps to take in the months before your trip. Please do not buy your airline tickets until you review the Flight Arrangements email.

Please follow this link to read our full General Tour Conditions.

With help from local experts and walking guides, these itineraries are hand-crafted with extensive on-site planning by WAI tour planners.

When planning Classic Curated Tours, our objective is to capture the essence of a destination–the history, culture, and natural wonders unique to that part of the world. We then build activities and walks that take us inside these characteristics.

Yes, these tours are educational, but they are also interactive and immersive; walking gets us off the bus and penetrates local cultures to not only see but touch, smell, and feel these special spaces.

Along the way, local walking guides amplify the experience by sharing insights into the magic of that particular location.

The official start and end point is our hotel in Williamsburg, Virginia. Travelers will fly into the Newport News/Williamsburg International Airport (PHF).

We recommend that you contact Laura Pfahler, the travel agent we work with, to help book your flight arrangements. In this age of airfare complications and airport uncertainty, using a travel agent is a good investment! More details about flight arrangements and travel agent contact information will be provided by email after you register for the Adventure.  Please do not book your airfare prior to receiving these flight details from us!

We generally walk at a pace of 2 to 3 miles per hour. Several walks on this trip are oriented more towards education, and therefore take longer due to stops for guide commentary. Nature walks, on the other hand, generally continue at a steadier pace because we’re stopping less to talk.

In most cases, we are not “strolling.” We are walking at a relaxed but steady pace. Your experience will be significantly affected by your level of physical fitness. If not walking regularly at home, we strongly recommend that you make a priority of “training” beforehand in order to both enjoy the trip and avoid medical issues due to overexertion. If you have questions about your ability to participate, please call our office at 1.800.779.0353.

We have adopted a walk difficulty rating system which contains a numeric indicator for trail incline and an alpha indicator for trail terrain. The explanation for this system is presented on the table below:


1. Minimal hills or stair climbing. Cumulative elevation gain: <200 feet.
2. Some moderate hills and stair climbing. Cumulative elevation gain: 200-1000 feet.
3. Some significant hill or stair climbing. Cumulative elevation gain: 1000-2000 feet.


A. Almost entirely on pavement.
B. A significant part of the route is on well-groomed trails with very few obstacles.
C. A significant part of the route is on somewhat difficult terrain (rocky / rooted paths or soft sand).

WAI believes strongly in the importance of travel insurance for financial and medical protection from any number of unforeseen circumstances that can arise before departure or during your Adventure. This is now especially true in the era of COVID-19, which is typically treated like any other illness for travel insurance purposes. Many travel insurance providers are available for you to consider. Laura Pfahler and Sharon Mitchell of World Travel Inc. are travel agents who provides air travel and insurance services to many WAI travelers.

Check out Insurance Tips from World Travel for a short introduction to travel insurance. (NOTE: WAI receives no commission or financial remuneration from World Travel Inc.).

As always, do some shopping to ensure you are getting the best value. Using the SquareMouth.com website can be a good way to compare pricing.

Other options include:

  • Allianz
  • Betins
  • Travel Guard
  • Travel Insured International

NOTE: We suggest purchasing from a reputable, well-established insurance company (avoid buying insurance from an unknown company found only online). Travelers interested in purchasing “cancel for any reason” insurance coverage should be careful to check pricing and terms BEFORE they register for a tour. Recent changes in the international travel landscape have caused changes in the policies of some insurance companies, and made the purchase of this particular type of policy even more time-sensitive.

Walking Adventures International reserves the right to cancel this tour departure with fewer than 12 participants, in which case registered participants will receive a 100% refund of payments received. This refund policy contains one exclusion related to the COVID-19 outbreak. Many suppliers require non-refundable deposits as a condition of booking services. Unforeseen circumstances linked to the virus can force us to cancel a tour. Due to these supplier’s non-refundable policies, WAI intends to retrieve as much of these deposits as possible, but cannot guarantee a 100% refund. In cases where full refunds cannot be obtained for a cancelled tour, we will do our best to transfer unrefunded money as traveler credits to be applied to a future tour to that destination.

View our full Coronavirus FAQ for more details

The Our Approach to Fun but Prudent Travel document identifies and explains Covid-19 mitigation policies and procedures WAI is using as a starting point for our 2021 tours. Because the knowledge base about COVID-19 changes daily, we review these policies and procedures on an ongoing basis, and will, of course, notify travelers on tour of updates as we approach the departure date of your tour.

Contact our office with any questions at 360.260.9393 or [email protected].

During this age of COVID-19, WAI evaluates reports and conditions on an ongoing basis. Please read Our Approach to Fun but Prudent Travel document before signing the COVID-19 Travel Waiver. Participation in this tour requires your signature on the COVID-19 Travel Waiver.

Contact our office with any questions at 360.260.9393 or [email protected].

Upon registering for this Adventure, you will receive a welcome email and initial invoice notifying you of your tour balance and due date. You will be able to make that payment online or over the phone as well. Any other payments necessary for optional services or one-off decisions can also be made this way.

Upon registering for this Adventure, you will receive a welcome email and initial invoice notifying you of your tour balance and due date. You will be able to make that payment online or over the phone. Any other payments necessary for optional services or one-off decisions can also be made either way.

A Flight Arrangements email with critical information on booking your flights will be sent soon after registration, as well as important steps to take in the months before your trip. Please do not buy your airline tickets until you review the Flight Arrangements email.

About 70 days before departure, you will receive a final statement reminder about the final tour payment, which is due 60 days before departure. Once paid, the final tour payment is non-refundable. Please see our General Tour Conditions for the full terms and conditions for participation in this Adventure.

Around 2-3 weeks before departure, you will receive a final email packet with details of the program, including hotel names and contact information, a list of fellow travelers, and a more detailed daily schedule.

We hope you’ll join us to experience Christmastime amidst the lights and sparkling festivity of historic Colonial Williamsburg!

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Williamsburg Colonial Christmas 2021