Our Family Trip to Williamsburg

Lifestyle Travel

Hey Fam! What a sweet time it’s been over the past couple months getting situated in our new home and new life in Texas. With the craziness that has been 2020, I feel like there’s no place I’d rather be than with my sweet family. Baby #2 is coming in less than 2 months (omg that feels like tomorrow), and we are so excited to see Teeny in action with her baby sis! I’ve noticed in this season that the pace of our lives is going to change in a few months, so we’re trying to soak up as much undivided “Teeny Time” as possible. When Visit Williamsburg invited us to enjoy a family getaway in August for a fun trip to tour the area, we felt like it was a sweet prayer answered. We took a four-day getaway (for the first time in months!) as a family and got to visit some of the incredible areas that Stevie grew up visiting (his parents are originally from Virginia and Maryland).

We flew out a couple of days early to enjoy some beach time, and it was so fun to see Teeny light up for the ocean! I didn’t realize how much she missed it!!! My favorite part of the entire trip was when we visited all the attractions in Greater Williamsburg. When we arrived at the Kingsmill Resort, it was so peaceful with an incredible view overlooking the water. We stayed in a condo which felt like our little home away from home. It was amazing because it gave Teeny plenty of room to breathe and run around! It was also so close to everything we wanted to see including all of the sites and delicious restaurants we planned in our itinerary, and had amazing amenities of its own including a top championship golf course (for Stevie) and a gorgeous spa with amazing services (for me haha).

I loved walking through Jamestown Settlement and seeing the tiny houses people used to live in and walking through an old but beautiful church. Suddenly all the stories in U.S. history were coming back to life! It’s crazy to think that THIS is where those first settlers lived, and it was mind blowing getting to see the things that have been preserved and left behind. I’ve personally never been to a place like this before, and for Stevie, it had been years since he went, so a lot had changed. There was so much to see and everything we did was family-friendly, which was perfect for Teeny who LIVES for a good adventure (as you can see from all these cute snaps from our trip!). 

Speaking of Teeny, her favorite activity was definitely the Pirate Adventure Sail we did in Yorktown through Yorktown Sailing Charters. It’s a kid-friendly pirate cruise that lasts about an hour and a half! The crew members dress up as pirates and put on a fun little performance for the kiddos out at sea. It was awesome!  

On a totally random but not random note, I ate half my body weight in some of the BEST seafood I’ve ever had. YUMMMMY. My favorite restaurant we went to was Waypoint Seafood & Grill because it had a cozy yet family feel, and the seafood was so fresh! I got the shrimp and scallops and Stevie got the flounder – we always share so we were both sneaking bites from each other’s food! There were honestly so many good local eatery spots (I loved the fun dinner we did at Revolution Golf & Grille because we got to play virtual golf (kid-friendly!) and eat some delicious bites while we played.  We also visited the cutest antique shop called Lightfoot Antique Mall & Country General Store. If you’re an antique nerd like Stevie and I, then you will love that they have over 35 vendors to pick from and so many cute trinkets! We ended up finding the cutest vintage candle holders (a set of 5) for $15 total! Score!!!!

There was just something so special about this trip that brought our family closer together. I don’t know if it’s because we will be a family of 4 soon (5 if we’re counting Sweetie!!), or the fact that this trip was so much more appreciated because we haven’t traveled in so long. We definitely soaked up every minute. Stevie’s mom also came along to help us with Teeny, so it was a blast watching her and Nana in action and hearing fun stories from when she grew up in the area.

We definitely can’t wait to go back. There’s so much to see in the Greater Williamsburg area and it’s continuously growing with new sites and attractions. It was easy on me (being 6 months pregnant at that time lol) and bringing a toddler with us who is still talking about some of the things we did and saw. Oh teeny <3

If you’re looking for recommendations, here’s a short list of our itinerary and everything we did! If you’re planning a trip to Greater Williamsburg or looking for a fun family getaway, these spots are must. Special thanks to Visit Williamsburg for helping us plan our family vacay!


Kingsmill Resort & Spa


Berret’s Seafood Restaurant & Taphouse Grill

Mobjack Bay Coffee Roasters and Petite Cafe

Carrot Tree Kitchens Yorktown

Revolution Golf & Grille

Blue Talon Bistro

Gabriel Archer Tavern at Williamsburg Winery

Waypoint Seafood & Grill

Duck Donuts

Hound’s Tale


Pirate Adventure Sail in Yorktown 

Charlie’s Antiques

Lightfoot Antique Mall & Country General Store

Tour Colonial Williamsburg

Jamestown Settlement

Tour American Revolution Museum at Yorktown

Hope you enjoyed this little travel diary. Love you fam! 

Thank you Visit Williamsburg for sponsoring this post 🙂

comment tweet like pin



Leave a comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

  1. This is just the perfect trip with family. In the recent events due to covid travelling is almost stopped for many such post really admire and give us a hope to roam. Hope you enjoyed a lot. Lots of love 🙂

  2. Cool photos! And the city is wonderful! Thank you so much for this post – really like it!) Keep up the good work, good luck.

  3. I love reading your blog, and this one was no exception! The seafood sounded absolutely divine, and your photos are gorgeous. Thank you for sharing a little bit of your life with us! I’ll have to make a trip to Williamsburg myself. My son finally helped me get a mobile medical alert system, which means I can start exploring the wonderful state of Virginia again. 🙂

powered by chloédigital
Read previous post:
Easy, Healthy, Delicious Meals for the Whole Family

Hey fam!! I hope you’re having the most beautiful day...