4 Days in Kentucky

Spent my birthday weekend in Kentucky for the Kentucky Derby!! I grew up riding horses & ever since I was a little girl, I DREAMT of going to Kentucky Derby weekend. I would record it on TV each year and replay it all week. 9 year old Tessie would be over the moon knowing she finally made it!

But the best part? Not only did we get rained on, but my birthday weekend has turned into this tradition where me, mom, and grandma take a "3 generations" trip. Honestly, can't think of a better way to celebrate another trip around the sun.

Lexington is famous for being the Horse Capital of the World! It is also the second-largest city in Kentucky and offers a surprising blend of history, art, and natural beauty. While Kentucky might not be at the top of everyone's travel list, Lexington stands out as a vibrant and engaging city worth exploring. This 4-day guide will help you make the most of your time for an unforgettable weekend packed with unique experiences. From the city's rich history and southern cuisine to visiting the several horse farms, Lexington promises a fun adventure for everyone!

Day 1:

• Travel day! We flew into Nashville because it was a lot cheaper being that Kentucky Derby weekend is busy!

• Rental car from Enterprise Rentals (we drove to Lexington, which is not far at all!)

• Bloom & Brew Coffee

• Spent the day in Nashville (3 hours from Lexington, KY) and shopped at boutiques!

Day 2:

• Old School Coffee House (my personal FAV coffee shop from the whole trip! they have school themed drinks like dirty school counselor lol!)

• Churchill Downs for Kentucky Derby Weekend (fun fact: if you ever plan to go to the Kentucky Derby, do not get scared by the ticket prices!! your ticket comes all inclusive with foods and alcoholic drinks or regular drinks!!)

Day 3:

• Black Swan Books

• Downtown Shops! Honestly so fun and so many neat and fun things to see and do!

• Missy's Pies (HOMEMADE PIES and AMAZING!!!)

• High on Art and Coffee (the BEST homemade sandwich shop!!!! 11/10!!! We each LOVED it and will be dreaming of these sandwiches!)

• Create Studio (you can make your own candle here and get creative with it!)

• Keeneland Horse Race Track

• The Black Market Boutique

• Calypso Boutique (my fav out of all of them for a very aesthetic and chic style)

• Peplum Boutique

• Monkee's Boutique

• Leestown Coffee House

Day 4:

• Third Street Coffee (they have Kentucky Derby Themed Drinks after racehorses)

• Kentucky Castle

• Kentucky Horse Park (you get to meet retired race horses and feed them peppermints)

• Vinaigrette Salad Kitchen (SO YUM!!!!)

• Ramsey's (the best home cooked southern cuisine and they give huge portions)

Advice:

• Don't think that you need to plan extremely in advance for the Kentucky Derby. We literally planned everything out only 3 months ago. Hotel, tickets, rental car, everything! Our horse race ticket was about $150 each but so WORTH it because it comes all inclusive with all you can eat food and drinks. The drinks even come in a cute glass that can be used as a souvenir! The hotel was about $170 a night and the rental car was a total of $242 for the entire time. Overall, it was a very decently priced trip!

• If you are going to buy tickets for the Kentucky Derby in the future, BUY THE BLEACHER TICKETS!!!! The best view and 1/5 of the price for the covered tickets. Also, don't wear heels! Even though it may go better with your outfit, there is so much walking that you do at the derby that everyone who goes, wears sandals.

• Also, do a rental car!!! So much easier to get around and driving around Kentucky is so rewarding and gorgeous!! You get the most amazing views of the horse ranches and the endless white fences!!

As always, if you need any help at all, reach out to me! I love to help you all out!

XOXO, Tessie Ledesma