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Do not joke about college in front of Lindsay

We are complete amateurs with this whole road trip thing. Neither of us care to drive – to the point where we were joking before we left whether or not we could even last the entire four months we are planning to be on the road. Because of our shared dislike of driving we decided to “chop” up the trip as much as possible. You know, keep the drives short. No more than five or six hours of driving in a day if possible. The first leg of the trip, from Chicago to Washington DC, was going to be an anomaly. But it still kept us up at night thinking about driving for 12 hours straight. Shockingly that drive went really smooth.

Right before we took off we both mapped out a very loose and tentative schedule. Our route would take us through Shenandoah National Park, perhaps a stop around Charlottesville, a journey down the Blue Ridge Parkway to Asheville, a visit to Lindsay’s Aunt Karen just south of Charlotte, short trip to Columbia (South Carolina) for an SEC football game, on to Charleston – then maybe Hilton Head or Savannah. It sounded great. The longest trip was the drive to Asheville and according to our research that was only going to be about five hours. Boomshakala.

Wellllllllllllll we are sort of terrible at planning. At least right now. The wineries we thought we’d visit along Skyline Drive were much more out of the way, we didn’t book any accommodations after Washington DC thinking that “oh, it’d be fun to wing it” – which, it is. BUT, and a big but, you shouldn’t wing where you are going to stay over Labor Day weekend in a National Park. That night we had to sleep in our car in a parking lot for a lodge just off the road. In the morning we hopped on our bikes, road to their campsite and took a shower. It was fun, but not as smooth of an operation as we’d thought it would be. And the next night – forget it. Not going to happen. The park was jammed and we tried to secure an Airbnb near Barboursville Winery. Nope. So at 4pm on Sunday of Labor Day weekend we were in the same spot we were the night before. No place to stay. Luckily we were only a 30 minute drive from Charlottesville – home of the University of Virginia.

We’re scared, we’re tired, we’re confused – and we’re sleeping in the car. It’s not the best shot in the world, but essentially the back seats of our Mazda Tribute fold all the way down, we filled up and air mattress and settled into our five star accommodations.

Don’t Make College Jokes

Not a ton of availability for hotels in Charlottesville. I should say not a lot of hotels within our desired budget in Charlottesville. After driving to a few spots, calling a few others and growing impatient we landed at The Cavalier Inn. This hotel, set right smack in the middle of the University of Virginia campus is run by some group that returns all the profits back to the university. Cool.

I can’t explain why, but as we made our way slowly through Charlottesville, I was cracking myself up yelling a bunch of stuff out the car window to all of the students running around campus with their book bags and sporting equipment. I’m coming up with pure classics like:

“Hey, can you help me find Professor Scheimerheimer’s Psych 101 class??”

“Where is the keg tonight?”

“I have a copy of the exam, do you want to buy it?”

“I’m totally going to have to drop a class, I am like taking 18 credit hours right now, Bro…”

I’m loving life, cracking myself up and generally just having a blast. Life is real good at this point. I turn to look at Lindsay expecting her to also be enjoying what is happening, hoping maybe she’d even throw something out there too, but to my astonishment she was stone-faced. Not even an ounce of enjoyment. In fact maybe even upset. Turns out Lindsay does not care for any type of collegiate-themed jokes.

I am laughing. Laughing hard. Trying to figure out where the party is tonight, do I need to wear a yoga or will their be jungle juice at this place. Lindsay meanwhile is having an awful time sitting next to me with this face.


So Thomas Jefferson lived just outside of Charlottesville

And we were told that we absolutely could not pass up the opportunity to visit Monticello, his home in the mountains just a few miles from the University of Virginia campus – which he founded. It is a gorgeous estate. Monticello in fact means something like “small mountain” and that is exactly where his is located, on top of a small mountain with beautiful 360 degree views of the surrounding landscapes. A lot of trees have grown tall since the house was built but you can still see parts of the Virginia campus from certain angles while you are on the property.

The tour was great, the man built a nice house and was really smart. His library has books in 8 different languages, he drafted the Declaration of Independence at the age of 33, was the ambassador of France for a while and of course served as our countries president for 8 years. No doubt about it that this dude was operating at a level just a bit above where most of are able to.

Behind us are some very well kept vegetable gardens. In it’s prime Monticello was operating as a 5,000 acre farm. Almost all of the ingredients needed to prepare the meals were sourced here. Today this garden stretches almost 1,000 feet in length. This was very, very impressive.


Awesome house. Designed by Thomas Jefferson himself. Maybe not the best interior designer (unfortunately they didn’t allow photography on the inside and we were with a tour guide) — but believe me, Thomas J. is a better architect than decorator.


Here is the back of the house. Also awesome. We were on a garden tour at this point but didn’t last very long. It was coming up on our third hour at the estate and frankly we start drifting after a little bit. The guide was incredible, but too technical for our pedestrian brains to digest at this point.

But there was something else that caught my attention. The very first thing the staff on the grounds recommends you do prior to taking the shuttle up to the house where you will take a guided tour is to watch a short 15-minute film that will serve as an introduction to Thomas Jefferson and the estate at Monticello. The film was really well done. Touched on the aforementioned Jefferson accolades, how the grounds were selected (he was born just a few minutes away and fell in love with the area as a child) and gave credit to the men and women who were responsible for the construction and maintenance of the estate. And here is where it became interesting.

You see, the video (and really your entire time at Monticello) is one big Jefferson love fest. And, rightfully so. Like I said, pretty incredible guy. However there was one big glaring contradiction and the folks running Monticello didn’t even attempt to hide it. They presented quotes from Jefferson such as this one “there is nothing I would not sacrifice to a practicable plan of abolishing every vestige of this moral and political depravity.” and then the next second would talk about how he had somewhere around 120 slaves working on his property and that at his death he only freed 5 – which are assumed to be his children too. This wasn’t exactly called out in the history classes I took as a kid. Turns out TJ was very outspoken about slavery and how it was terrible and this and that but owned a shit ton of slaves. WTF? Kudos for the people running the show here for not trying to hide this, but it was so weird. I was laughing and thought to myself that not a whole lot has changed in politics in the last 200 years or whatever.

The verdict on Virginian Wines

One of the things we were excited to check out were all the wineries that dotted the Skyline drive in Virginia. I’ve heard either through reading stuff online or through other people that Virginia was producing some real quality wine and it was just a matter of time before they took the market by storm. Kind of like Napa before we all knew it as Napa. I’m no vino expert but this did get me excited. And Lindsay too. We made our way to 3 wineries.

  • Sharp Rock
  • Du Card
  • Barboursville

Maybe we didn’t go to enough wineries, maybe we picked the wrong ones – whatever it was …I don’t know, but I wasn’t that impressed. The wineries are bit more spaced out than in Napa or Sonoma so it’s not super easy to visit a bunch in a day (we did three over two days) which made it a bit less convenient and hard to make it to a ton without spending days in the region. There were a couple of good wines, but for the most part we didn’t come across any spectacular wines for less than $60/bottle – which I don’t know…just seems like that shouldn’t be too hard to pull off. If you have $60 and walk into a Binny’s in Chicago chances are you’re going to walk out with a bottle of some pretty dang good juice. Don’t get me wrong — we had a fricken blast. Just the actual wine didn’t quite compare to their competition on the west coast.

Love this view from Sharp Rock. This is a shot looking north west back towards Shenandoah National Park.

Barboursville winery, just outside of Charlottesville, is responsible for helping put Virginia wines on the map. Their flagship Bordouex-inspired Octagon wines are aged in these decorated French Oak barrels before being bottled and sold. Yum. This stuff was really, really good but you couldn’t touch a bottle for less than $55. Their older vintages were selling for over $100

Just another day at the office.

R.I.P. Grandpa

Sadly, my Grandpa passed away only a few short days ago. May he rest in peace.

4 thoughts on “Do not joke about college in front of Lindsay

  1. Pingback: The best pictures of our trip (Part 2 - Central & North America) - Jeff & Lindsay's Travel Blog

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