American Experiences: Explore Williamsburg

Road trip through historic Virginia

Travel back in time in Colonial Williamsburg and discover how our forefathers spurred the American Revolution. Experience era-styled dining and day-to-day living while strolling through the oldest towns in America.



per person


Each American Experiences trip is designed for you to craft and customize your own adventure. Pick your own date, add or remove nights, upgrade your car, reverse cities, add on activities, and more. Our team of adventure experts has curated suggestions to make your trip incredible, and our team is standing by to assist you in creating your incredible adventure.

While crafting your road trip, be assured that your package includes centrally-located hotels, a Hertz car rental, breakfast daily, free hotel WiFi, and an adventure all your own.

*Above pricing quoted is per person, land, and air from Chicago.

Suggested Itinerary

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Day 1: Arrive in Williamsburg

Make your way to Williamsburg, a city that played a historic role in the American Revolution. Check in to your hotel then get acquainted with the surrounding area, especially the heart of it all: Colonial Williamsburg, a historic district and living history museum. A good place to start is Merchant's Square. Parking is available, and within the surrounding blocks, you'll find numerous boutique stores, cafes and restaurants.

Day 2: Williamsburg

Colonial Williamsburg is the world's largest living history museum filled with skilled artisans, actors, building tours, and notable events that transport you back to the 18th century. Your included tickets give you access to historic buildings, the art museums, and a complimentary shuttle for transportation around the property. After seeing The Governor's Palace, The Bindery, The Capitol Building, and Wetherburn's Tavern and Charleton's Coffee shop, you may have worked up an appetite. Why not join a walking food tour of the area that gives an inside look at what makes the local food scene so good: gourmet mac 'n' cheese, baked goods, and flights of beer all await!

Day 3: Jamestown

There's plenty more to see. Perhaps you'll visit the Jamestown Settlement and relive the experience of being part of America's first English colony. Climb on board a replica of one of the three ships that sailed from England to Virginia in 1607. Other activities include Virginia Beach, Busch Gardens, and Watertown USA. You can end your adventure tonight with a Colonial Conspiracy Tour that teaches you some of the lesser-known accounts of the nation's forefathers and includes stops at haunted houses, burial grounds, and a discovery of the more sinister side of the area.

Day 4: Williamsburg

Today, have plenty of time to travel unscripted! Perhaps take a stroll around the Williamsburg Botanical Gardens or kick back and relax in a 15 ton salt cave at the Williamsburg Salt Spa. Or, flash back in time again by heading to one of the many taverns, such as King's Arms Tavern, still operating from the 1700's - it's up to you to make your own adventure!

Day 5: Farewell

Time to head home. Be sure to grab some hand-cooked Virginia peanuts for the ride!

Add-On Adventures

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Williamsburg Walking Food Tour

Spend the afternoon eating your way through Williamsburg. Explore the neighborhood and meet some stars of the local foodie scene. The tour will take you to a handful of restaurants, specialty food shops, and producers where you will taste everything from gourmet mac n' cheese and Blue Talon Bistro, to a selection of baked goods from Justified Bake Shop, to a flight of local beers from Green Leafe Café, and so much more. Get an inside look at what makes the food scene so cool and bookmark spots to return to.
$76 per person

Williamsburg Craft Alcohol Tasting Tour

Get to know Williamsburg's craft alcohol scene on a 3.5-hour, small-group tour of the area’s top breweries, distilleries, and a meadery. Taste honey and mead, locally crafted spirits, and a craft beer flight while touring the facilities, meeting local brewers, and learning about how the local industry has grown. Choose to grab a bite to eat at a variety of food trucks along the way (own expense) and relax with all the logistics worked out for you and your guide as the designated driver.
$81 per person

Colonial Conspiracy and Dead of Night Ghost Tour Combination Ticket

Forget the mundane stories you learned in your high school U.S. history class and discover the lesser-known accounts of the nation’s forefathers on a 1-hour conspiracy tour. The atypical walking-tour takes place at night, after the large crowds of tourists have departed. Follow your in-character guide to Williamsburg’s top landmarks and listen to the controversial history surrounding each of them. Then take an eerie stroll through the dark evening streets of colonial Williamsburg on this top-rated ghost walking tour. Follow your costumed, in-character guide through the shadowy lanes and squares by candlelight, and discover the sinister side of this historical town. Stop to see haunted houses, burial grounds, and other spooky sites as your guide tells tales of 18th-century ghosts, skeletons, apparitions, and secret vaults and tunnels.
$21 per person


American Experiences: Explore Williamsburg



Unscripted experiences, insider access and authentic local flavors

Our team of travel specialists and local contacts have curated some of the best, most exclusive and authentic experiences, restaurants and accommodations to truly immerse yourself in a way that wouldn't be possible in larger groups or just on your own.

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