Those who have enjoyed Williamsburg, Virginia, before know one thing for sure: It’s not a vacation to be skipped. That’s especially true when it comes to skip-gen travel, and there’s plenty for grandparents traveling with grandchildren to do, see, and eat. From adventure to history and from culture to nature, this multi-dimensional must-do offers something for everyone on a multi-generational trip.

Jamestown Ships Multi-Generational Family

Create new memories while honoring the past 

Teach without ever sitting in a classroom at living history museums like Colonial Williamsburg, where the past comes to life in a symphony of colors, sounds, and tastes. Listen to the clop of hooves from a horse-drawn carriage, the melodies of a fife and drum corps, and get hands-on with the wooden toys and games that delighted kids decades before electronics – or electricity. Visits here are all about immersion and choice. Some kids may want to assist farmers, bakers, and carpenters with immersive behind-the-scenes experiences with tradespeople; others who are into dinosaur fossils will dig hands-on opportunities to participate in archaeological research that reveals life in the earliest days of the Virginia colony. 

Put a unique – and spooky – spin on your blast from the past with a teen favorite: a Williamsburg Ghost Tour. The after-dark guided trek brings to life legends and lore that haunt landmarks like the Governor’s Palace and the College of William & Mary. 

Ghost Tour Social - Blog Image

There’s more fun in store in Jamestown and Yorktown. Historic Jamestowne is an archaeological treasure trove where families can walk in the footsteps of Pocahontas and John Smith at the original site of the first permanent English settlement in America. Children’s programming is just as fascinating for grandparents long removed from their history-class days, and costumed interpreters engage with their audiences to regale all ages with stories about what it was like for local Native tribes who frequented the settlement. 

Stroll a bit forward through time – 168 years, to be exact – when you and the grandkids hit up the American Revolution Museum at Yorktown and Yorktown Battlefield. Kids can compare how different their family camping trips are from a re-created Continental Army encampment and muster with troops, getting hands-on with how they farmed, cooked, and ate. Inside, films like “The Siege of Yorktown” on a 180-degree surround screen bring the boom of cannons and artillery to life in thrilling fashion with special effects. 

Enjoy fun for all seasons

While the living history museums at Colonial Williamsburg, Historic Jamestowne, and the American Revolution Museum are open year-round, there are lots of opportunities to balance the pace of outdoor fun with indoor experiences at Williamsburg’s many art museums. Kids especially delight in the 19th-century toy display at the Abby Aldrich Rockefeller Folk Art Museum. Grandparents can take it all in with the Littles on an exciting scavenger hunt through three exhibits at the Art Museums of Colonial Williamsburg.  

Museum Multi-Generational Family

Don’t miss an opportunity to be the “cool grandparents” and add STEM lessons into the mix onboard a roller coaster at Busch Gardens® Williamsburg. The adventure park’s grounds reflect the region’s rich colonial history – albeit with ground-breaking science used to design the brand-new Pantheon, the world's fastest multi-launch coaster. There’s plenty for younger kids to do here, too, with lots of rides for shorter children and a zoo with opportunities to meet and greet all things feathery and furry. 

Make more skip-gen magic at Wagsters Magic Theatre, where illusions, card tricks, and audience participation make for myriad “wow moments” (and, seniors enjoy a ticket discount). 

Parks and recreation for all ability levels, interest

The great outdoors awaits all ability levels, for those who want a relaxing stroll or those who want to take it to the next level – literally – at a zipline adventure course

The Virginia Capital Trail offers 52 miles of scenic paths for discoveries on foot or on two wheels. Bicyclists won’t want to miss out on a chance to rent some wheels and pedal past some of the region’s must-visit sites along the way; shorter, kid-friendly suggested itineraries that hit up Jamestown Settlement, Chickahominy Riverfront Park, and Freedom Park

Freedom Park combines rich history and adventure as one of the first free Black settlements in America. Today, three historically accurate cabins re-create what life was like for slaves emancipated before the Civil War. Within Freedom Park, Williamsburg Botanical Garden beckons little kids and grandparents who want to explore 800 species of Virginian vegetation, marveling at the butterflies floating throughout a pollinator’s Shangri-La. Also within, older kids can float through the air at Go Ape Zipline and Adventure Park, where aerial crossings and obstacles, rope ladders, net bridges, trapezes, and zip lines await those who want to indulge their inner Tarzan. 

Girl on zipline at Go Ape

Paddlers and anglers won’t want to skip the serenity of Waller Mill Park, where paddleboat rentals, fishing, hiking, kayaking, and disc golf awake those seeking serenity on a 360-acre lake.  

Food, glorious food

Worked up an appetite or already enjoyed food for thought and ready for something to satisfy the stomach? Williamsburg’s got no shortage of opportunities to savor and indulge – even if your little eaters are picky.

It’s just as much a feast for the eyes as a lunch to remember at Shield’s Tavern in the heart of Colonial Williamsburg. The 18th-century building hasn’t changed much since it opened as one of Williamsburg’s original taverns, and today, servers in period costumes keep that going with hospitality as warm as the comfort food coming from the kitchen. 

Casual, family-friendly fare awaits in Merchants Square at The Cheese Shop, where you can pick up sandwiches and cheese boards for a picnic or check out passersby with outside seating. 

Merchants Square Shops

Those craving pancakes or burgers will want to head to Shorty’s Diner for a walk down memory lane — to the ‘50s, to be exact. 

And for those into playing with their food – playing games, that is – Food For Thought is an essential stop. The decor featuring the Founding Fathers, trivia cards on each table, and inspirational quotes in every nook and cranny are meant to spark conversation and engagement. The menu features kid-friendly options beyond the standard mac and cheese and chicken fingers, while 55-plus senior options, like crab cakes or meatloaf, are perfect for those with smaller appetites.

Getting here, staying here

Three international airports near Williamsburg make getting here easy. Checking family-friendly, accessible hotels and lodgings off the trip-planning to-do list is easy, too, since there’s a variety of options for all ages, budgets, and travel styles. 

For those who prefer not to drive a rental car, several options abound within walking or biking distance of Colonial Williamsburg (and they include two free tickets to the attraction, too, when booking directly). The Williamsburg Inn and Williamsburg Lodge each have outdoor pools and access to an indoor pool, with ADA-accessible guest rooms and elevators. The Griffin Hotel offers oversized rooms with plenty of space for the Grands and Littles to spread out, and despite its proximity to the heart of Williamsburg, it has shuttle service to the historic highlights, art museums, and Merchant’s Square. Each of those offers babysitting, too, for when Grandmom and Granddad may need a quick break. 

Kids also love Great Wolf Lodge’s indoor water park with waterslides and a toddler-friendly play area. Grandparents with teens and tweens who want to hit the green for a little tutorial won’t want to miss the luxury guest rooms, two- and three-bedroom condos, or rental cottages at Kingsmill Resort, where there are 36 holes of championship golf and three swimming pools — a true hole-in-one for skip-gen family memory-making.