Attending the Kentucky Derby and Kentucky Oaks in Style

This past weekend I spent time with my parents, Mrs. Jeffsetter and some friends at the 140th Kentucky Derby in Louisville, KY. This was my first time attending the derby, and it almost didn’t happen because of my own negligence.

But it did happen, and it was awesome.

A little background on getting Kentucky Derby tickets

I have always wanted to go to the Kentucky Derby, but I also figured it would be difficult to get tickets. A friend of mine signed up on the Kentucky Derby website to get early access to tickets for the 2014 running.

In November he received notice that pre-sale tickets would be going live on the site the next day. He was not sure if he would be able to make it to the derby, so he gave me access to his account to go in and try to secure tickets on pre-sale.

After waiting in a ticket lobby for a while, I was finally able to get in and choose seats. Not much was available that was of note, but I ended up being able to book a box seat of 6 tickets that appeared to be the best value. I use the term value loosely, because these tickets were still super expensive and cost 20% above retail price as part of the pre-sale. Whatever, this is something that Papa Jeffsetter has always had on his bucket list and we had the opportunity to go.

Attending the Kentucky Oaks and Kentucky Derby

Our tickets entitled us access to both the Kentucky Derby on Saturday and the Kentucky Oaks on Friday. While we all know about the Kentucky Derby, the Kentucky Oaks is another race that is quite popular with people from Kentucky. We used our day at the Oaks as a dry-run for the madness that would ensue the next day at the Derby.

It was tough work consuming Mint Juleps and wearing pink clothes to support breast cancer, but someone had to do it. Here are some photos of the experience.

The ladies looked beautiful in their specially picked out hats for the occasion!

You might say I cleaned up nicely as well

I even managed to take a terrible red-carpet selfie.

And survived the long gambling windows

Took some venue photos for perspective

And managed to have a few of the signature drink of the Kentucky Derby. You know, because I wouldn’t be a good travel blogger if I didn’t go the traditional route.

I even snuck in a taste of Pappy Van Winkle, which is often hard to find

One more Selfie

And another photo with my and Papa Jeffsetter. We’ve come a long way since we were in South Africa 2 weeks ago!

Leaving Kentucky a Winner

I managed to take a little video of the actual race before they left my line of sight. Surely you can see my horses!

I lost every bet that I had made this weekend until the actual Kentucky Derby. I bet on California Chrome to place and Danza to show, which combined won me 2x my original bet. I didn’t leave Kentucky a rich man, but it was good to go out a winner!

If you are interested in going to the Derby, you might as well sign up for the ticket pre-sale now so that you can be notified when tickets go on sale later this year.