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Road Trip to Williamsburg: Trip Review and Lessons Learned

Sometimes vacations don't go as planned. Sometimes you have to make last minute adjustments and it can be very disappointing. I am actually quite proud of myself for keeping my cool through all the problems we encountered along the way and embracing alternative fun. Sometimes adversity can be just as fun. Here's how our trip unfolded.


We left Maryland around noon on Friday, our drive down was about what we expected. Between DC and Richmond the traffic is never great. Doesn't seem to matter what time we leave that stretch of road is slow going. It's important to have car entertainment planned. We did not. At the last minute we decided to take Pat's car not mine and thus his phone was connected not mine and we were unable to listen to Harry Potter. Instead we listened to Taylor Swift all the way down. That's what my husband gets for taking his car not mine. On the way back we listened to the Imagine Dragons station in compensation.

We arrived in Colonial Williamsburg around 4 PM and headed straight to Raleigh's Bakery. It's about a 10 minute walk from Merchant's Square and you get a nice view of the beautiful homes, shops, and taverns, both original and reconstructed along Duke of Gloucester Street. You can see the horse drawn carriages pass and the historically dressed docents. The bakery always has hot or cold cider depending on the weather and my favorite ginger cookies that I buy in bulk. We grabbed our goodies enjoyed them in the little courtyard behind the bakery, feeding the birds while we snacked.

We always try to arrive in Williamsburg before The Cheese Shop closes at 6 PM, because I simply must have my corned beef sandwich and delicious dill pickle. We also get wine, cheese and charcuterie to enjoy back in our hotel. The cheese shop has one of the most impressive cheese collections I have ever seen outside of France. I highly suggest you ask the clerks for their recommendations and get a variety to try. They will cut them down to any size for you to enjoy. They also make cheese plates to enjoy in the square paired with a bottle of wine from the shop. In the basement there is a wine shop and bar. It's changed considerably since our last visit in December of 2019, but I found both a Rose and a Cabernet Franc from Virginia to enjoy during our stay. Pro tip: you can order online for quicker service on sandwiches.

We stayed at the Fairfield Inn and Suites, a Marriott Hotel, that is centrally located to all the places I had planned on visiting this trip. We've stayed in this location before because they have multi-room suites. We also have enjoyed the Residents Inn that has a kitchen as well. Both serve complimentary breakfasts. I have to stay we weren't particularly happy with our stay at the Fairfield, but I am unsure how much of the problems were Covid related, though lack of staffing was definitely apparent. At this point I would hesitate to either recommend or deter you from staying at this hotel but I think we'll be looking at alternative lodgings in the future. We tend to stay in Marriotts, due to my husband being a gold elite member for life but now that I am a travel agent we have more options for great hotels and find you one.


We had been watching the forecast all week. We knew it would rain but we weren't sure how bad the storm would be until Friday. We texted back and forth all week with my brother-in-law, afraid of not seeing them of not using our date specific tickets and non-refundable private cabana at Water Country USA. At the time we purchased the tickets, it was significantly cheaper to buy the date specific tickets and we really only had that day to use them so it seemed like a good idea. I booked the expensive cabana in advanced because I was afraid they would sell out. We needed the limited 6 person private area to try and keep Scarlett a little safer than sitting in the giant wave pool amphitheater of lounge chairs, where socially distancing would have been tricky. If she weren't so high risk this wouldn't be necessary but we were nervous and pulled the trigger. I feel like I made a poor choice and my husband feels we would have regretted it more if we had gotten there and felt unsafe.

We spent early Saturday trying to come up with a safe way to see our in-laws. Scarlett hadn't seen her cousins since 2019 and this seemed like the most important part of the trip. It was my brother-in-law who suggested, after we had failed to come up with outdoor kid friendly ideas, Top Golf in Richmond. We were a bit hesitant as we had just gone to Top Golf a week ago and neither of us are golfers, but Scarlett was thrilled. You send a kid to golf camp once and she wants to be Tiger Woods, sheesh. We got two bays so we weren't on top of each other and had a good time. Pat got to see his brother and Scarlett her cousins. I had $4 mimosas, so everyone was happy.

After the outing to Top Golf in Richmond, an hour from our hotel, we rushed back to move our stuff to a new room. A large part of our dissatisfaction with the Fairfield was a problem with our original room and how they handled getting us a new room. They couldn't move us till 2 PM which was fine but when we returned at 1:30 they were moving our stuff without discussing it with us. I am not trying to throw the staff under the bus but remarking on a lesson I learned through this process. Check your room carefully when you arrive. Make sure the water heats up in the shower, if you are looking for an allergen free room check the pillows, check the lights, etc. In a non-pandemic situation it probably isn't as big of a deal to find out late something is wrong but as staff was short resolving our issue quickly was impossible. When they told us they could move us at 2 PM the next day we should have asked more questions and discussed how and when our baggage and contents of our fridge could be moved. Hope for the best but planning for the worst is a key motto for a pandemic vacation.

The rain began to slow so we decided to head to Walmart, grab a new card game and some warmer sweatshirts and go to a local vineyard. This seemed like a great idea at the time until the flood happened while we were at Walmart. Getting to our car and back to the hotel was a monumental disaster. We were soaked to the bone. We needed to stay put for the rest of the afternoon. Fortunately we had ginger cookies, cheese, prosciutto and wine. Oh and two new card games: Llamas Unleashed and Trash Pandas. We turned on The Great British Baking Show and had a blast playing games. I kept thinking that while this was not the plan if we had been home and some event had been rained out, we would have retreated to our corners of the house and not had such fun family time.

My favorite thing about the Fairfield Inn was always how close it is to one of our favorite restaurants. I know when you think about Colonial Williamsburg you immediately think great Thai cuisine. Ok maybe it's not the first thing to come to mind but it is to us. Our in-laws, who went to William and Mary, introduced us to Bangkok Garden over 10 years ago and we never skip it. The duck curry is to die for. I will take a personal recommendation (and I have many to give) over a yelp review any time. The rain stopped so we walked back to the hotel, hopped in the car and headed to the outlet mall. We never miss an opportunity to buy more Under Armour. Insert crying laughing emoji here.


Our final day started out well. We grabbed our delicious coffee from Aroma's in Williamsburg, where they always have fresh baked biscotti, a true love of mine. We got our steps in, under cloudy skies and the intense humidity that follows a storm like Saturday's, walking the Colonial Williamsburg streets before meeting my in-laws for brunch. While I do love history and have taught it, Williamsburg is a stroll down memory lane. We've spent so many holidays there, celebrated our engagement and had fun summer vacations. It just brings me joy. We did not go into any of the historic buildings or engage in experiences this time round as I wasn't comfortable with Scarlett in small indoor spaces but I can't wait till we can.

Brunch is almost always at Barrett's. It's a fantastic seafood restaurant where yes, I get a non-Maryland style crab cake. It's a bit of a novelty as it's made with more bread crumbs and is seared a little more on the outsides but I enjoy it and the ports in that area of the Chesapeake outdate ours here in Baltimore. They know what they're doing even if it's different. Finally, no trip is complete without treats from Wythe Candy Shop. They have every time of candy good you can possibly imagine or eat on the car ride home.

The trip home presented another covid related problem. We had intended to meet some friends outside of Fredericksburg, VA at a vineyard. But half way there I realize I the vineyard was by reservation only since the pandemic started and I didn't have one. We called our friends and agreed to meet at Ingleside Vineyard in Oak Grove, VA. Unfortunately, a snafu with Waze, let me make a strong plug for Google Maps over Waze here, we ended up on Oak Grove Rd in Fredericksburg, VA. We had a tough call to make: drive another hour to meet our friends and have much needed wine or head home. We hadn't seen our friends in some time so we went for it and accepted the extra hour drive. We quite enjoyed both the Rose and Pinot Grigio at the vineyard, along with our cheese and salami we brought with us from The Cheese Shop, and of course the company.

I wish it had been smooth sailing home but traffic was miserable and we were exhausted when we finally arrived home. Despite all the troubles, Pat looked at me in the car and said "I'm glad did this, I had a lot of fun." This statement is literally what I live for in this business. I want people to have fun on trips I plan. My heart was bursting with joy that I could plan and execute, even with problems, a trip that would allow him to see friends and family, and quality time with me and Scarlett. Let me help you plan your trip to Williamsburg, VA. Both my good and bad experiences serve to fuel me with knowledge to help you have a great vacation.

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