If there’s one thing I’ve learned as a grandmother, it’s that time spent with family is priceless—especially when it involves a little adventure. This fall, I took a trip to Williamsburg, Virginia, with my daughter and two granddaughters, and it turned out to be a magical blend of history, fun, and bonding that we’ll be talking about for years.
My granddaughters, now 6 and 9, are at such a fun age for traveling. They’re curious, energetic, and at that perfect stage where everything feels like an adventure. When the opportunity for a girls' getaway popped up during their school fall break, I knew we had to make it happen.
My granddaughter Emilea, who's in fourth grade, is starting to dive into American history, so it felt like the perfect opportunity for the four of us to bond while discovering a bit of the past together. And what better place than Williamsburg?
Day One - Felicity Joins the Adventure
Our trip had a unique twist: we brought Felicity, the American Girl doll! If you’re unfamiliar with her, Felicity’s story is set in Colonial Williamsburg, and my granddaughters were eager to explore the very streets and houses their beloved doll "grew up" in. Before our trip, the girls read about Felicity's life in the 1770s, making everything much more exciting.
Where to Stay
We stayed at the exquisite and historic Williamsburg Inn, which is an experience in itself. The Inn is impeccable and has such a rich history. I couldn't help but think about all the incredible stories the walls must hold. We were excited to learn that previous guests included Queen Elizabeth and Winston Churchill. Even the Rockefellers have stayed there. However, the girls were more impressed that Shirley Temple celebrated her 10th birthday there! How's that for a bit of history? I couldn't help but think that my granddaughters would be telling stories about this visit one day.
Our suite was perfection—each night, we returned to freshly turned-down beds, chocolates for the girls, and cordials for my daughter and me. The room even had fresh-cut flowers. Not to mention, the service at the Inn was beyond attentive.
Historic Walking Tour and Dinner at Christiana’s Tavern
On our first evening, we took a short walk to Colonial Williamsburg, where we met with Trish, our tour guide from Williamsburg Walking Tours. She made the past come alive and led us on a fascinating guided tour. Even more impressive was how Trish connected historical facts and locations to scenes from Felicity’s books. I saw my granddaughters' eyes light up as they imagined Felicity walking the same cobblestone streets.
We finished the tour just steps from Christiana's Campbell’s Tavern, a charming restaurant. We dined by candlelight to mimic the historical feel. George Washington himself frequented this famous tavern, and they say he loved stopping by for their fresh seafood—and I can see why!
Another popular dish is their pea soup, made with marjoram, mint, and green onion. Of course, I had to try it—along with their famous crab cakes—and let me tell you, I'm so glad I did.
Day 2 - A Morning in Colonial Williamsburg
One of the things I loved most about this trip was how picturesque it was. Williamsburg has a way of capturing time and beauty. After an elegant and delicious breakfast at the Terrace Room right inside the hotel, we spent our morning frolicking through the beautiful courtyard and gardens at the Inn, watching the girls dance in and out of the flower-lined walkways.
Next, we strolled through Colonial Williamsburg and Merchants Square. Walking from the hotel to Colonial Williamsburg was a great way to explore on our own. Merchant Square is lively, with charming shops, outdoor taverns, and restaurants. The fall weather was perfect, and you could feel the energetic buzz in the air. Lunch at the Cheese Shop was a must—delicious, fresh, house-made sandwiches. Oh my goodness, did they hit the spot! Of course, lunch wouldn’t be complete without stopping next door at the Wythe Candy & Gourmet Shop. Watching my granddaughters carefully choose their candies felt like witnessing a ritual of childhood.
A Little Magic and Adventure
We added a bit of magic to our trip with an afternoon at The Wagsters Magic Show. The girls loved the mid-afternoon break in the day to catch this fantastic performance. The Wagsters are a sweet, young married couple, and their love for each other shines through in their spectacular show. What made the show a blast was their interaction with the entire audience. The girls were captivated, especially when my eldest granddaughter, Emilea, was invited on stage to help with a trick. The look of excitement on her face was unforgettable! I highly recommend this show for families visiting Williamsburg—my granddaughters are still talking about it and even took home their very own magic tricks.
The fun didn’t stop there. We also played a competitive round of mini-golf at Pirate’s Cove.
We ended our day with a great experience at Revolution Golf and Grille. What an incredible place! They have private golf bays with simulators and interactive games, offering plenty of options for all skill levels. We all got involved in a hilarious round of fighting off zombies with zombie dodgeball. We might’ve (virtually) broken a few windows in a round of golf (without any real damage, of course!). Needless to say, they are ready to go back again!
Day 3 - Exploring Jamestown Settlement and Busch Gardens
On day three, we dressed, ready for another exciting day. We began with breakfast at the charming Blue Talon Bistro located in Merchant Square. This cozy, French-inspired bistro is known for its comfort food. My daughter and I ordered the omelet with black forest ham, mushrooms, and Swiss cheese. Yum!
A Day of Discovery at Jamestown
We visited the Jamestown Settlement, a highlight for all of us. The interactive exhibits and outdoor living history displays were incredible. The girls boarded replicas of the ships that first brought colonists to America, and their curiosity was in full swing. We lost track of time imagining what life was like for those early settlers. The girls adored this museum, especially with its courteous staff ready to answer their many questions. We probably spent more time there than planned, but it was worth every minute!
Our visit coincided with a special exhibit featuring Ruth E. Carter costumes from movies like Black Panther, Coming to America, and Selma—a treat for all of us!
We headed toward the river for lunch and found a charming spot right off the beachfront. Coastal Thirst is the perfect place to grab a bite before setting sail.
Our afternoon sail along the York River with Yorktown Sailing Charters was a dream. We soaked in the historic scenic views and learned a few fun facts from the friendly crew members. The girls were in awe as dolphins swam alongside the boat, and my six-year-old granddaughter Evelyn even sang to them! It's one of those moments I’ll treasure forever.
After the cruise, we couldn't resist returning to Merchants Square and Colonial Williamsburg to shop for souvenirs. We couldn’t leave without taking home a few keepsakes to remind us of this fantastic girls' trip. We walked into the William Pitt Store to purchase a new dress for Felicity (handmade in Williamsburg, of course) and to Prentis to purchase an authentic quill feather and ink.
A Perfect Ending
No trip to Williamsburg is complete without a visit to Busch Gardens, and we surprised the girls with a night at the park. The Halloween decorations added a spooky touch, and while I’m not one for roller coasters, my daughter and her eldest, Emilea, braved the rides. Meanwhile, I strolled the decorated streets with my younger granddaughter, Evelyn. The icing on the cake? They saw the northern lights from the top of a ride! It was a magical end to an unforgettable trip.
On our last morning, as we headed to the airport, we stopped for a tasty breakfast at yet another quaint little restaurant called Hohl. This is a spot I will never forget, as their breakfast is made with the freshest and healthiest ingredients. Not to mention, I left there with the best cup of coffee I've ever had.
Why You Should Go
Looking back on this trip, I'm reminded of the special bond that mothers, daughters, and granddaughters share. This vacation brought us even closer together.
Don't wait—take the time to make unforgettable moments with the ones you love.
The town offers a charming mix of culture, fun, and adventure. We came for the history but left with so much more—laughter, stories, and moments that will stay with us forever. So, if you’re dreaming of a getaway that offers a bit of everything, Williamsburg is calling your name.
