Williamsburg Travel Diary

Visit Williamsburg

All the summer feels! We just got back from our incredible trip to Williamsburg, Virginia…I can’t begin to tell you how AMAZING it was to travel (even domestically) again. This was my second flight in over a year and Jeff’s FIRST – can you believe that? We were lucky enough to visit Williamsburg, Yorktown, and Jamestown, and loved every second of it. Let me share our full itinerary and photos from the weekend. We planned our entire stay with Visit Williamsburg!

Day One – Arriving & Checking-In

We flew into Richmond, VA from San Francisco on Thursday and landed around 5 p.m. There weren’t any direct flights from SFO to Richmond, so we flew through Charlotte! It was extremely easy through American Airlines. Jeff booked a car for us that was big enough for all of us to fit into – a big Infiniti SUV because a lot of the sites are a 10-15 minute drive away. Richmond is about 1 hour from Williamsburg, so we drove into town!

Visit Williamsburg

We checked into our hotel once we arrived – Williamsburg Lodge, Autograph Collection. This hotel is so charming and very central to all of Colonial Williamsburg, including shopping and dining available in Merchants Square. It was SO much fun to stay right in the heart of the living history museum. We walked to and from the main square’s shops and restaurants every day. The rooms were adorably decorated, too. We were able to stay in a little stand-alone section of the hotel which was very quiet and perfect for us. We booked two adjoining rooms so that Emma and Walker could have their own space, but we could still all be together. Highly recommend staying at the Williamsburg Lodge if you are heading to Williamsburg for a vacation.

Visit Williamsburg
Winter Blues Jazz Festival

Later that night we wandered from the hotel over to the Winter Blues Jazz Festival hosted downtown. It was FANTASTIC – the live jazz band was incredible and we were treated to a charcuterie board and wine. What more do you need?! As the name suggests, typically this festival is held in the wintertime – but it was rescheduled to the summer due to COVID. Jeff and I had a blast dancing the night away. It was the perfect beginning to our trip.

Visit Williamsburg Jazz Fest

After the Jazz Fest, we walked over to Merchant Square to have dinner at Amber Ox Public House. It is a farm-to-table restaurant that serves American food and has amazing reviews… we LOVED every bite. The girls ordered Frosé (frozen rosé) – how fun is that?! The food was absolutely delicious. Definitely make reservations in advance here because it was extremely popular and full even around 8:30 p.m.

Visit Williamsburg
Visit Williamsburg

Day 2 – Historic Yorktown

Visit Williamsburg

Day 2 was a FUN-filled day! Williamsburg and the surrounding areas are full of history, and we decided to spend most of the day over in Yorktown (about 20 minutes from Williamsburg). It was founded in 1691. It was awe-inspiring to be somewhere so critical and important to the American Revolution.

Visit Williamsburg
Visit Williamsburg
Visit Williamsburg

Our first stop was Mobjack Bay Coffee Roasters in the Historic Cole Digges House. This cafe was not only absolutely adorable but also full of history. They actually offer professional historian-guided tours through the national park battlefields and historic buildings nearby! The house itself is quite significant as it has been a coffee shop/tea house for hundreds of years. The hardwood floor inside is original! Quite amazing if you ask me. They also have a resident ghost who lives upstairs and enjoys sitting in a chair facing the window. The coffee and breakfast was yummy and a great way to start our day!

Visit Williamsburg
Visit Williamsburg
Visit Williamsburg
Visit Williamsburg
Visit Williamsburg

After breakfast, we headed to the American Revolution Museum at Yorktown where we dove into the history of our Nation’s founding. They have a living history museum with actors dressed up in period clothing…it was SO interesting. Jeff and Emma are big history buffs so they were in heaven.

Visit Williamsburg
Waterstreet Grille Visit Williamsburg

For lunch, we ate at Water Street Grille! It was so beautiful to sit by the stunning York River on a picture-perfect day. The weather was warm while we were there with barely any rain…which was perfect! You can’t ask for much more. The food at Water Street Grille was yummy! Everyone ordered salads except for Jeff. ;) Shocker!

Visit Williamsburg
Visit Williamsburg
Visit Williamsburg

Our next adventure was one of the highlights of the entire trip. The four of us jumped aboard the Schooner Alliance by Yorktown Sailing Charters. We had a relaxing sailing tour of the historic trading route. Super easy to grab tickets (just head straight to the boat at sail time to buy tickets) and we loved learning more about the history of the area. It was gorgeous! The day was perfect, and the river was pretty calm. It’s such a wonderful and must-do activity while visiting Yorktown!

Visit Williamsburg Yorktown Bookshop
Visit Williamsburg
Historic Georgetown Visit Williamsburg

After our sailing adventure, we headed back to the cute little Riverwalk area of Yorktown and just walked around…the shops are adorable. We loved relaxing and seeing everything this area has to offer.

Visit Williamsburg
Cochon Restaurant

Later that night, we decided to try a delicious French restaurant that everyone has been raving about online back in Williamsburg! It’s called Cochon on 2nd…and when I tell you it was amazing…it really was AMAZING. The girls tried some incredible drinks – one tasted like pears and the other was sorbet-flavored. Talk about mouth-watering. Everything was perfect and watching the chefs prepare everything in the open kitchen was really fun for us. Another must-do!

Day 3: Ziplining & Historic Jamestowne

Visit Williamsburg Go Ape
Visit Williamsburg
Visit Williamsburg Ropes Course

We woke up on the morning of our third day and chose chaos! I had never been ziplining before so we thought it would be a fun family activity to try Go Ape Williamsburg. They have a full adventure park with lots of zipline courses to try out…I still can’t believe we ended up doing this. It became one of the highlights of the entire trip…

Jeff, Walker, and I took part in the adventure course while Emma played the part of photographer for us! We spent an hour zipping through the trees and going through their obstacle courses. SO MUCH FUN! I officially beat my fear of heights, too. ;)

Visit Williamsburg
Go Ape Williamsburg

After our crazy morning, we headed back to the hotel to change and freshen up before going to Gabriel Archer Tavern at Williamsburg Winery. It was wonderful driving through the bright green roads & vineyards…felt like we were back home in Napa a little bit. The food at the Tavern was seriously delicious. I ordered the Sundried Tomato Risotto, and everyone was jealous. SO yummy! We were going to sit outside under the wisteria, but it rained a bit, so we sat inside. Still so nice!

Visit Williamsburg Winery
Williamsburg Winery

After lunch, we drove over to Historic Jamestowne which was the first permanent English settlement in America. They have an American Indian exhibit including Pocahontas’ belongings that were found on site…it was fascinating. Settling here in Virginia back in the 1600’s was not easy…we viewed many burial sites and where the actual settlement would have been/looked like. They are preserving this site and currently digging for more archeological finds. They also have live actors depicting what life was like back then.

Visit Williamsburg
Historic Reenactment
First English Settlement

After our visit to Historic Jamestowne, we spent the rest of our day and evening at Busch Gardens. We LOVE roller coasters and theme parks so this was a blast by itself, however…we were really there to see Kool & The Gang live in concert for the Summer Nights concert series kickoff. It was AMAZING!! This was our first live show since before COVID and everyone was in the best mood. Not only were the guys wonderful at singing but the entire crowd added that extra celebration vibe. ;) Busch Gardens elevated this trip so much…We rode roller coasters and ate delicious BBQ until the park closed. Perfect ending to another special day.

Visit Williamsburg
Kool and the Gang Concert
Busch Gardens Virginia

Day 4: Final Day

Truffled Eggs
Brunch in Merchant Square

We decided to have the BEST brunch ever on our last morning at  Blue Talon Bistro. It was just a quick walk from our hotel to Merchants Square – which allowed us more time to view Colonial Williamsburg. So many beautiful spots to check out and walk through. Once we arrived at Blue Talon, I was instantly transported to Paris. This place is just DARLING (and can I mention the blue paint is too cute…should I add it in our new home?!) and the food was seriously incredible. As soon as we sat down, we were surrounded by delicious pastries and coffees galore. The staff was so sweet they made our morning…One of our best meals, for sure!

Horse and Buggy colonial Williamsburg
Governors Mansion
Colonial Williamsburg Gov Gardens
Colonial Williamsburg

We walked through beautiful Colonial Williamsburg after breakfast for a few hours – shopping, touring the Capitol and Governor’s Palace, and just admiring the largest living museum in the world. Big Bridgerton vibes from this place…and we LOVED every minute of it. We then toured the gardens of the Governor’s Palace and found them stunning. The maze was our favorite…even though we got lost and needed the help of a 7-year-old to lead us out. :)

After this, we had to catch our flight home. I can’t believe how fast this trip went. It felt so good to come back to my home state of Virginia and show my family why it’s such a special, fun place to visit. It’s not only jam-packed with history but filled with beautiful towns and the kindest people. Williamsburg was the perfect getaway for us this summer and I’m so happy we able to plan this trip!


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7 thoughts on “Williamsburg Travel Diary

  1. Thank you, Kristy!! Definitely saving this one 🥰 you guys should try Old Town Alexandria VA next! Same vibes and so much to do!

  2. Thank you for sharing photos and comments on your trip. It looked like a lovely way to vacation with the family.

  3. Hi Kristy!

    So love all of your pictures of the Williamsburg area! Having lived there for nearly 20yrs, it’ll always hold a special place in my heart!

  4. Looks like so much fun! Thanks for taking us along to a beautiful place I would never see otherwise! So glad you were all able to enjoy it together!!