How to Have the Absolute BEST Multi Generational Family Trip in Colonial Williamsburg 2018

One difficult thing about visiting a new-to-you travel destination is finding the right activities for your extended family. This was my challenge when we took our first multi generational family trip to Colonial Williamsburg! I hadn’t been before and as with every family vacation we take, I tend to do a lot of research around where to go, what to eat, what to see, etc…

Sometimes though, this due diligence isn’t enough. This is the case at Colonial Williamsburg, because it’s such a large attraction with tons to see and do and there’s really no way at all to account for absolutely everything.

Wouldn’t it be great though if you had a dedicated tour guide to help plan your family trip to Colonial Williamsburg?  Someone who has visited several times throughout their lives, eaten at all the restaurants, stopped in all the shops and walked every single cobblestone of the property?  

What if you had resources for the entire family to help you both before, during and after your vacation or ideas on what types of things you can bring home from your family trip to keep the vacation memories alive for your family throughout the year?

Well, you’re in the right place!  Read on to learn how to have the best multi generational family trip to Colonial Williamsburg!

Multi Generational Travel Guide for Colonial Williamsburg

this post contains affilate links and includes product in exchange for an honest review 

After reading Debra Bailey’s A Colonial Williamsburg Love Affair, I am 100% convinced that this is the only Colonial Williamsburg travel guide anyone would ever need. Even if not visiting Williamsburg, it’s an incredible look back at the history of the time and chronicle of the era!  

Bailey’s book covers Colonial Williamsburg in two parts.  The first 21 chapters are a journal of her visits from age 10 in 1965 through the years including 2011 – 2016.  We’re able to learn more about her family, her parents and children and feel as though we’re growing and aging and growing and learning right along with her family. 

Later, the last 14 chapters are devoted to actual travel tips when visiting Colonial Williamsburg with your family; where to visit, what shops to pop in to, what you can expect when you get there…   Her depictions make you feel as though you’re right there hearing the ‘ting, ting’ of the blacksmith working iron in Anderson Blacksmith Shop.  

My favorite part of A Colonial Williamsburg Love Affair are the small, often missed details Bailey offers, like where to find tucked away spots to relax; detailed instructions on what little side streets to turn down, landmarks you’ll pass to get to them and what time of day to best stop for a break from the elements.

These are invaluable tips often left out of travel guides that mean so much to breastfeeding moms and parents of children with sensory issues.  


Video – Family Trip to Colonial Williamsburg – YouTube: Crazy Busy Fit Mom


Debra Baily offers insider tips for grandparents on the best time to go to Colonial Williamsburg with grandkids, recommends programs and offers suggestions on budgeting for a trip.  After reading the book you’ll see how Colonial Williamsburg has something for everyone and any age; even those not interested in history!  


How to Get Kids Excited about Colonial Williamsburg

Whenever we prep for a family trip, I always try to incorporate educational elements to our vacation.  When we visited Colonial Williamsburg and Yorktown Visitor Center I brought along some books for our road trip and purchased Powhatan Indian Safari Ltd Toobs as well as the Jamestown Settlers Toobs.   

By bringing the hands-on aspect of the history to life for my youngest son, he was more engaged during the trip because he was already familiar with many of the sights that we came across. This is especially important on multi-generational trips because the more interested the youngest members of the family are, the better time Mom, Dad, Grandma and Grandpa can have.


Check out the above-referenced books by clicking on the links below!

  1. D is for Drums: A Colonial Williamsburg ABC
  2. If You Lived in Colonial Times
  3. The Colonial Caper Mystery at Williamsburg
  4. Goodnight Virginia



Bring a Bit of Colonial Williamsburg Home With You

After the bags have been packed back up, laundry washed and put back in place and the house brought back to relative order, it’s always fun to bring home something that evokes strong memories of family time together with grandparents and grandchildren.

One such way is by bringing something delicious back home from Colonial Williamsburg, and what could be more delicious than chocolate?

Mars Chocolate North America has partnered with Colonial Williamsburg and other historical sites across the United States AMERICAN HERITAGE® Chocolate.

The chocolate is fashioned off ingredient lists from the 1750’s, but also to educate consumers on the history of the Americas through the unique lens of chocolate.  Did you know that cacao beans were used as form of currency dating back to the Aztec Empire?


Christopher Columbus brought cacao beans back to the Spanish court in the early 1500s and George Washington drank “chocolate cream” at breakfast while Benjamin Franklin sold chocolate in his print shop. Chocolate has traditionally been included in military provisions throughout history – these are all things you can learn when visiting historical sites that sell AMERICAN HERITAGE® Chocolate.  Colonial Williamsburg is one such site, where you can purchase the drink mix and chocolate blocks.

I was excited to have the opportunity to try AMERICAN HERITAGE® Chocolate recently and with my youngest, went right to the kitchen to whip up some Chocolate Peanut Butter Whoopie pies!  We found the chocolate flavor mild and delicious, the perfect accompaniement to the rich peanut butter filling.

Now, if you can’t get to Colonial Williamsburg with your extended family any time soon, rest assured American Heritage Chocolate is available on Amazon



Taking a family trip to Colonial Williamsburg or a similar living history attraction  is something I believe every family should try do at least one time in their lives.  Colonial Williamsburg in Virginia, Conner Prairie Pioneer Settlement near Indianapolis, and Old Sturbridge Village in Massaschusetts were among the first to adopt living-history as a way to bridge the historical gap.

Living-history for most is a welcomed, hands-on sensory experience; a way to learn about the past through full immersion and it’s one that we love using to incorporate homeschooling into our family travel trips. Visiting Colonial Williamsburg offers a concrete connection to our roots and the foundation of our country.

Have you visited Colonial Williamsburg or a similar living-history attraction?  If so, comment below and let me know which one!

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