Southern Road trip.

Southern Road trip.

I’ve never really had an interest in going to the Kentucky Derby but this all changed. My boyfriend always wanted to go so he planned a Southern road trip for us. We had an amazing time.

Our journey begins with a short trip up to Chattanooga, Tennessee. I haven’t been to Tennessee in a while. Chattanooga is a small town in the Southeastern part of the state. We arrive and find ourselves at a quaint Airbnb. We arrive fairly late so we just do a quick look around downtown and have a drink near the Chattanooga Choo Choo. We have a quick bite at The Terminal Brewhouse which was fine, nothing to shout about. We return back to the house and fall asleep rather quickly because this was the only relaxed day out of our three day vacation.

Another one of the rooms at Miss Mary Bobo’s Boarding House.

We wake up later than planned as always and begin our trip over to the Jack Daniels Whiskey Distillery in Lynchburg, Tennessee. Before, we drink we must first eat. So we eat at the most Southern restaurant I’ve ever encountered. Miss Mary Bobo’s Boarding House. A real experience our host, was a pleasant lady and had a ton of information on all that happened inside of the home. The restaurant was so adorable. Upon arriving to our room, The Motlow room. (Named after Mr. Lem Motlow, the favorite nephew of Jack Daniels, who would later inherit the company.) The host had several drink options for us, Sweet Tea, Unsweet Tea, or water. After that it was a very family dinner type situation where we all passed our food to the left in order for everyone to get a little bit of something. The lunch lasted about an hour and then we were off to the distillery. A short walk through downtown Lynchburg and we arrived at the distillery for the Angel’s Share tour. We then toured around the distillery and at the end got to taste a flight of 5 different kinds of Jack Daniels Whiskey. The tour was a bit boring, but the whiskey tasting came with a free Jack Daniels cup, which made it worth the 25$ entry.

The first whiskey in the flight.

We are always in a rush, so after the distillery we go take a look at the Old Moore County Jail. This two cell jail held the infamous Jesse James.

After that a jump in the car and were off to Nashville, Tennessee. We’ve both been to Tennessee plenty of times. Never to Nashville, though. A pop into our Airbnb to put our stuff away and then were on an open bus tour of the city. With a very knowledgable tour guide we learn a lot about the city.

The tour is over and we are off to Broadway! I’ve been to many cities with a main street but nothing like this. Beale Street and Bourbon, even Ocean drive, or any street in Atlanta can’t compare to this. Amazing crowd of people and we were just there on a regular ol’ Friday night. We decide to eat at Jason Aldean’s Honkey Tonk. The food was very good, the service, eh not so much. In the waitresses defense it was very busy. We were one of the last group of tables in the middle of the floor before they started clearing the tables for what I guess was supposed to be the dance floor. We finish up eating and depart. To check out a few more Honkey Tonks and go back to our Airbnb. Tomorrow is the day we’ve been waiting for.

It is Derby Day and we are so excited! We wake up later than usual (of course) and are rushing to Churchill Downs. Pit stop at Starbucks, and were on our way to our hotel, which is just outside of Louisville in a city called Elizabethtown. A change into our outfits and were on our way!

Click here to get my watch!

Like my dress? Click here to purchase it!

Enter: Churchill downs, we go on over to the general admission side which is where all the fun events are. Have the iconic Mint Julep and purchase a little bit of Derby Merchandise. It starts raining, of course. So we check out a couple indoor things before we head on over to 2nd/3rd Grandstand. Our seats were a whopping $900.00 each! Plastic folding chairs outside at this price is unbelievable! We went to the wagering windows and placed our bets. We bet on Maximum Security, #7, and Tacitus, #8. Fast forward to minutes later, Maximum Security is declared the winner. We hurry on over to the wagering windows to collect our winnings. After sometime in line we wonder what’s going on. MAXIMUM SECURITY has been disqualified due to obstruction of another horse. Country House is now declared the winner! Country house literally had no chance of winning this race. Safe to say we only ‘won’ $30 thanks to Tacitus, who came in 3rd place. We really did not win anything, because we spent way more than that!

We depart Churchill Downs to head on over to see what Downtown Louisville is all about. We end up at The Galt House hotel. A 4 star hotel with 6 Star prices. The hotel was $999.00 for that night. We didn’t stay there, but we checked it out because we were going to eat at Down One Bourbon Bar. The host was friendly and we were seated right away. No one checked on us for sometime and we were getting frustrated. The restaurant was not busy, to our surprise considering this was Louisvilles time to shine. It’s the Derby weekend, for crying out loud! Our waitress wasn’t good and neither was the food. We skedaddle up on outta that place real quick! Our next stop is the casino! My fav! A short while, and more money wasted were outa there! Turning in for the night back at our hotel in Elizabethtown.

Wake up early, back on the road to Nashville, once again! This time to enjoy the Country Music Hall of Fame! A beautiful building, but not a whole lot of interactive things to do, it is still a must do on your bucket list!

Back on the road again after the museum and a 4 hour journey to Hartsfield Jackson Atlanta International Airport, and I’m on my way back to Orlando for a 3 day trip the next day. All of the activities we’ve done on our southern road trip is one that I believe everyone should do at least once in their lifetime, especially The Kentucky Derby. Would love to hear everyone else’s experiences as well!

Back on the road again after the museum and a 4 hour journey to Hartsfield Jackson Atlanta International Airport, and I’m on my way back to Orlando for a 3 day trip the next day. All of the activities we’ve done on our southern road trip is one that I believe everyone should do at least once in their lifetime, especially The Kentucky Derby. Would love to hear everyone else’s experiences as well!

Overall Nena’s Rating: 5/5

*All opinons are my own*

*This post is NOT sponsored*

*Disclosure: Some of these links may be affiliate links, at no additional cost to you, I may make a small commission*

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