Travel Diary: Williamsburg, Virginia

Williamsburg, VA trip itinerary

Williamsburg Travel Diary


My sister and I grew up visiting the Williamsburg area with our parents, because our godmother lived nearby and we just adore getting to see and spend time with her. Some of our favorite memories involve running around Colonial Williamsburg in matching outfits. 😊

So you can imagine how thrilled I was when I received the opportunity to showcase all that the Williamsburg area has to offer with the Visit Williamsburg team. They took note of some of our favorite things to do (hello eating and shopping 😉) and put together such a fun itinerary for us.

Our stay included three nights and two and a half days, and it was honestly the ideal amount of time for a mini summer getaway. We rarely leave our little beach town on Long Beach Island during the summer, but this was SO worth the trip. It’s perfect for a quick summer getaway or sunny adventure that includes it all– a beautiful hotel, outdoor activities, and divine dining.

We also felt incredibly safe in terms of COVID-19, since we were able to drive to Williamsburg and everyone there (from the hotel where we stayed to the restaurants) was obsessively cautious and clean. I also want to make a point to say just how kind everyone was throughout our trip. From the people who worked at the restaurants we dined at to the people who led the tours and activities we went on, we continuously encountered the most kindhearted people who wanted to chat and help us however they could.

Is it just something about people who live in the south?! Or maybe the Greater Williamsburg area really is just that wonderful and full of kind and courteous folks who made our touristy-selves feel right at home and welcomed everywhere we went… you’ll just have to visit and see for yourself!

The below button includes all of the resources and tips you’d need to plan a unique vacation that fits your interests. And below that you’ll find our personal recommendations for where we stayed, what we did, and ALL that we ate! I hope you enjoy and find this helpful when planning an upcoming trip in the area.

It seriously holds such a special place in our hearts and we highly recommend visiting whenever you can! xx

Where We Stayed

Williamsburg Lodge— We had the pleasure of staying at the Williamsburg Lodge, which is part of the Marriott  Autograph Collection Hotels, and my favorite thing about it had to be the location! It is located pretty much in Colonial Williamsburg and was only a half mile walk to Merchants Square, which you’ll see is where we did some of our eating and shopping. We stayed in a ‘Lodge Deluxe’ room that had two queen beds, and was lovely and very clean.

A few other perks that came with staying in the Williamsburg Lodge were the little coffee shop right off the lobby (called the Cupboard), as well as its spa (called the Spa of Colonial Williamsburg), as well as the three pools on the premises. It’s located right in front of the Williamsburg Inn, which I’ve heard phenomenal things about as well, and is also supposed to be a truly wonderful place to stay if you’re in the area.

Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary

What We Did

Shopping at Merchants Square— As soon as we arrived in Greater Williamsburg and checked into our room, we walked over to Merchants Square. The square is located at one end of Colonial Williamsburg and is shut down to vehicles so everyone may walk around. It includes an adorable 18th-century style shopping center with a variety of stores and restaurants. We stopped into Boxwood and Berry first, which sold such beautiful decorations and the most precious Williamsburg soaps (we picked up a few for gifts)! We also loved popping into Three Cabanas, The Shoe Attic, and The Precious Gem

Exploring Colonial Williamsburg— If you’re at all interested in history, architecture, or gardens, you will just lose it as soon as you step onto the premises of Colonial Williamsburg. It’s honestly like going back in time and being in a living, breathing colonial town. We’d recommend purchasing a day pass so you can access of all of the historic houses and see how they’ve been preserved and showcased to learn all about the time period. We ended up creating our own walking tour and our favorite stop had to have been the Governor’s Palace (and the gardens behind it!). Make sure to wear comfortable walking shoes and just wander around and take in all of the beauty of the colonial homes, stores, and people reenacting the time period!

Spoke + Art Provisions— On our first full day of the trip we spent the morning exploring Colonial Williamsburg and then had an active afternoon of biking and then paddle boarding. For the bike ride, we drove to Spoke + Art Provisions, which is a community gathering center that’s located right on the Virginia Capital Trail, which entails 23 miles of trail that runs from Jamestown to Richmond. We met the owner, Steve, (who was such a nice guy!) and rented two bikes and helmets from him. Then we set off on a trail that went across a bridge and beside a cornfield to Historic Jamestowne. It was very easy to navigate and follow the trail, and the path was smooth and totally manageable to bike, even if you aren’t a frequent biker. After our ride we returned back to the Spoke and Art building and enjoyed a cold drink from the little cafe that is on their premises. This is a cannot-miss activity if you like bike riding at all! 

Paddle Boarding— After our bike ride, we spent the remainder of the afternoon paddle boarding on Gordon Creek right off of Chickahominy Riverfront Park. The owner, Lori, is a fellow Jersey girl and such a wonderful instructor and guide when it comes to paddle boarding. We were scheduled for a two hour private paddle boarding session with her, but a few storm clouds began to roll in so we were only out there for about an hour, which was honestly the perfect amount of time to see the creek and enjoy the quiet beauty of the surrounding marsh and shoreline. This was such a peaceful and beautiful activity, that could very well have been my favorite thing we did the whole trip! 😊

Massage at the Spa of Colonial Williamsburg— On the morning of our final full day of the trip, we picked up a coffee at the Cupboard in the Williamsburg Lodge and walked across the street to the Spa of Colonial Williamsburg, where we both indulged in deep tissue massages! This was such a treat and relaxing part of the trip, and something I’d highly recommend after a particularly active day! You can also enjoy the three pools that are located right by the spa, which offer a variety of spots to lounge and take a dip when you’re staying at the Williamsburg Lodge or the Williamsburg Inn (one pool overlooks the Golden Horseshoe Golf Club course as well, which was just beautiful!). 

Shopping at Williamsburg Premium Outlets— After our morning at the spa, we headed over to the outlets for a little shopping… we popped into the J. Crew, Kate Spade, Le Creuset, LOFT, and Vineyard Vines. They have a ton to offer and you know we love a hunt for the best deal so this was right up our alley for a mid-morning activity. 

Segway Tour of Yorktown— Yorktown was the last area that we visited on our final full day of the trip, and it was fun to explore since we hadn’t ever visited before (whereas we had seen Colonial Williamsburg and Historic Jamestowne when we were growing up). This segway tour is such an awesome way to tour the whole area and it really is SO charming and fun to explore.

Shopping at Riverwalk Landing— We also did a little bit of walking around and shopping along the Riverwalk Landing part of Yorktown, which contains a variety of boutiques and restaurants. We found that if you walked from the riverfront up back into the town a little bit, you stumbled upon a few 18th century buildings that we just about flipped out over… it was an absolutely charming little area that is so worth walking around! If you want to head to the cutest spot, look for Mobjack Bay Coffee Roasters… truly such a pretty coffee shop located in a historic home.

Williamsburg, VA trip itinerary
Shopping in Merchants Square the first evening we were there
Williamsburg, VA trip itinerary
The Governor's Palace in the middle of Colonial Williamsburg
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Wandering around & exploring Colonial Williamsburg
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Heading into the Governor's Palace in Colonial Williamsburg-- there were no crowds at all!
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
The gardens behind the Governor's Palace
Williamsburg, VA trip itinerary
We had the whole place to ourselves!
Williamsburg, VA trip itinerary
On the bike trail from Spoke + Art Provisions
Williamsburg, VA trip itinerary
We rode through corn fields...
Williamsburg, VA trip itinerary
to Historic Jamestown
Williamsburg, VA trip itinerary
Paddle boarding along Gordon's Creek-- so beautiful!
Williamsburg, VA trip itinerary
A look into the Spa at Colonial Williamsburg's lobby
Williamsburg, VA trip itinerary
Segway tour at Patriot Tours & Provisions
Williamsburg, VA trip itinerary
Outside of Mobjack Bay, the cutest coffee shop EVER in Yorktown

Where We Ate

La Piazza— We enjoyed drinks and appetizers at La Piazza on our first night and so enjoyed it! It’s a quaint Italian-style restaurant located right in Merchants Square. We’d recommend the peach Bellini and the burrata!

Fat Canary— After we had a drink and appetizers at La Piazza during our first evening of the trip, we walked right across the street to the Fat Canary, which came *highly* recommended by my godmother, who lives not too far from the Greater Williamsburg area. I got the short rib and Jacqueline got the steak and she said that it was absolutely the BEST steak she’s ever had (and she’s a major steak lover so she’s had a LOT of steak… this is a huge statement of hers!). It’s definitely a nicer restaurant that is ideal for celebrating a special occasion or indulging in an extra nice (and DELICIOUS) meal.

Illy Caffe— This cafe is located in Merchants Square as well and was the perfect place to stop for a quick breakfast before exploring Colonial Williamsburg. The iced coffee was delicious, as well as the ham and cheese croissant.

Second Street an American Bistro— We went to this restaurant after spending the morning exploring Colonial Williamsburg, and it was such a wonderful spot to sit in the air conditioning and indulge in a really yummy lunch. The owner, Mickey, could not have been kinder and said that he has two daughters who were around our age (we reminded him of them! 😊) We’d recommend getting the onion rings (with a sriracha ranch dressing!) and the 2nd St ‘Burg & Blue salad! YUM.

La Tienda— On our second night of the trip we had tapas and sangria at La Tienda, which was only a ten minute drive from the Williamsburg Lodge. It was an adorable spot that offered such refreshing sangria and a variety of yummy tapas and paella dishes. Our favorite item on the menu had to be the garlic shrimp! SO good. 

The Cupboard— This was the little coffee shop located right off the lobby of the Williamsburg Lodge. We scooped up fresh coffee there each morning and they also had small bottles of wine or cider that you could pick up in the evenings as well. It was a very convenient coffee shop to have right on the premises of our hotel for whenever we needed a caffeine pick-me-up.

Oceans & Ale— We stopped here for lunch while we were shopping at the Williamsburg Outlets, and it just hit the spot! We ordered the seafood nachos to split and they were delicious. It was also a really convenient place to eat since it was also located right where the outlets were. A perfect mid-shopping stop!

Water Street Grille— On our final night of the trip we had dinner at this grill, which is located right on the York River in Yorktown. It was a really fun spot, complete with a circular indoor bar and outdoor patio. We enjoyed one of their orange crush cocktails and a wood-fired pizza. It couldn’t have been better to sit right by the water and enjoy the summer breeze there!

Williamsburg, VA trip itinerary
Merchants Square was were we enjoyed the majority of our meals!
Williamsburg, VA trip itinerary
Cocktails at sunset at La Piazza in Merchants Square
Williamsburg, VA trip itinerary
You have to get the burrata!
Williamsburg, VA trip itinerary
The Fat Canary right across from La Piazza...
Williamsburg, VA trip itinerary
Truly the BEST steak my sister has ever had!!
Williamsburg, VA trip itinerary
An iced coffee & croissant at Illy Caffe
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Sangria & tapas at La Tienda
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Williamsburg, VA trip itinerary
Enjoying an orange crush at the Water Street Grille
Williamsburg, VA trip itinerary

As I mentioned at the start of this post, we grew up running around here as little girls (giggling in coordinating outfits, of course), so it’s been such a dream come true to partner with Visit Williamsburg to share a place that we love so much.

Turns out it’s just as fun 20 years later 😉 & we are still matching & cracking each other up. 😂 I am beyond thankful to the Visit Williamsburg team for believing in me to tell the story of how much history, beauty, and yummy food the area holds, and what an ideal summer destination it makes, no matter what age you are.  ❤️ xx

Much love to Visit Williamsburg for sponsoring this post– all opinions are my own. And thank you for supporting the brands that support Amy Believes in Pink!

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Audrey Hepburn
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