Two Days in Louisville: The Perfect Schedule

What if you only had two days to spend in Louisville, KY? What would you do? How would you pack your days full of awesome? Louisville has so much going on that you would have to be very selective in order to get the best of the best during your short stay. I fear that you could possibly miss something if you’re not careful, but that, I suppose, is the fun of the challenge. Recently, a friend called me for the inside scoop on Louisville as he was planning a bachelor party. While the information below isn’t exactly what I told him for the bachelor party, his question made me think about my favorite things in Louisville, and what I would want someone from out of state to take away from their visit. Here’s what I came up with:


5:00 pm – LOUVINO – Appetizers & Drinks

Louvino is one of the best restaurants in Louisville with regards to both concept and taste. You will want to get a table around 5:00 just as they open so that you have time for a few small plates, and a wine or a bourbon before you head out on your adventure.

6:30 pm – CHURCHILL DOWNS – Night Racing

Churchill DownsWhen you’re traveling to Louisville, it’s impossible to ignore the home of The Kentucky Derby. The first post during night racing is typically around 6:00 pm, but who really wants to see the first race anyway? Get to Churchill Downs around 6:30 so you can start on the third race. Downs After Dark only happens about eight times per year, but it certainly makes for a fun evening. You don’t need any special tickets or boxes. You can pay the general admission or pay for a third floor ticket. Know how to bet.

9:30 pm – PROOF ON MAIN – Late Dinner & Drinks

21C Museum Hotel | Downtown Louisville | Statue of David

Proof on Main in Downtown Louisville is not only a delicious spot for dinner, but it’s one of the coolest locations in the city. Inside the 21c Museum Hotel, you will find this trendy spot with amazing food and cocktails. You can eat dinner until about 11:00pm, or you can sit at the bar and enjoy the limited menu until about 1:00am.



11:00 pm – OUTLOOK INN – Bloody Mary

The Outlook Inn on Bardstown Rd is well known for being a no-frills neighborhood bar with the best Bloody Mary in the city, and quite possibly, the world. You will find a solid selection of craft beer and bourbon here, but you can’t leave Louisville without enjoying one of their award-wining Bloodies. This is a great last stop for the evening. If you find yourself out a bit later than 11:00 pm, The Outlook Inn stays open until 4:00 am.



8:30 am – WILD EGGS – Breakfast

As Wild Eggs has broadened their territory, expanded into other areas of Kentucky, and even expanded into Denver, CO, I recognize that the original small shop that started on Dutchmans Lane has done something right. This place serves amazing breakfast, and while there are certainly other great breakfasts in Louisville, I decided that Wild Eggs has something for everyone. Do yourself a favor and get an “everything muffin” with your breakfast.

10:00 am – MUSEUM ROW ON MAIN ST – Culture Fix

mainstsluggerdriveway-e1420414100615That’s right, I think it’s important to fill your culture cup during a stay in Louisville. Something you should certainly plan is a museum tour. Located between 5th and 9th on Main St in central downtown Louisville, you will find ten fantastic attractions. Among these are the Frazier History Museum, Glassworks, The Muhammed Ali Center, The Louisville Slugger Museum & Factory, and The Evan Williams Bourbon Experience, and if you have kids with you, The Kentucky Science Center. The beautiful thing is that you can see 6 of these places with only one ticket. Or, you can pick your favorites and purchase individual tickets.

12:30 pm – FEAST BBQ – Lunch & Beers

Louisville has a good number of restaurants that crank out delicious smoked treats, but I have to say that Feast BBQ is one of my favorites when it comes to flavor and atmosphere. This place is absolutely fantastic, and it will definitely fill you up after a long morning of museum-hopping. Whether you get a sandwich, traditional meat with sides, or the amazing tacos, you will know why it’s important that you visit this restaurant when you are visiting Louisville.

2:00 pm – BARDSTOWN ROAD – Shopping

Shopping may not be my favorite activity, but sometimes you have to do it. The Highlands neighborhood offers some of the best shopping right on Bardstown Rd, a walkable corridor that runs through the middle of the neighborhood. Visit boutiques like Pitaya, Pink Door, General Eccentric, and Dot Fox. Check out Old Souls Vintage for some amazing finds, or head into Why Louisville, my favorite gift shop / novelty shop / crazy shop. Whatever you’re looking for, I’m pretty sure you can find it on Bardstown Rd.

4:30 pm – HOLY GRALE – Appetizers & Craft Beers

This is a great spot for delicious beers, and delicious food. It’s located in The Highlands, which is one of the coolest neighborhoods in the world. Holy Grale sources ingredients for their menu items from local and regional farms, and they have one of the most diverse beer lists in the city. They also have a fantastic outdoor garden area, so if it’s a nice day, you know where to sit. Grab any one of their appetizers and you’ll be happy, but you will want to try the beer cheese & pretzel, and the frijtes for sure!

6:00 pm – JACK FRY’S – Dinner

Walk across the street from The Holy Grale and enter into one of Louisville’s longest standing prized possessions. Jack Fry’s is a Louisville staple with its fabulous atmosphere, and spectacular menu. You feel the history when you walk in this place, and you can also see it documented in the historic photos on the wall. Jack Fry’s truly is a legend among the Louisville dining scene, and it’s a must when you’re visiting.
**WARNING – Weekend dinners at Jack fry’s are booked weeks, and sometimes months in advance. If you aren’t that prepared see below:

**6:00 pm – SEVICHE – Dinner

Seviche, a Latin Restaurant | Chef Anthony Lamas | Highlands

I use the excuse that Jack Fry’s books up early, which is true, but I honestly could not write this article without telling you to eat at Seviche. This is absolutely my favorite restaurant in Louisville. The menu is incredible, the wine list is exceptional, and the atmosphere is inviting. Eat one of their delectable Seviches for dinner, or get the Churrascos de Argentina. The flavors in these dishes will blow your mind, and this will truly be an experience to remember.

8:00(ish) pm – BIG FOUR BRIDGE – Sunset

11958033_10153725465424560_7567329258058106832_oThis old railroad bridge circa 1910 that crosses the Ohio River into Southern Indiana was reinvented as a pedestrian bridge in 2013. It’s a great place to look over the Louisville skyline, and it’s also the best place to watch a sunset in Louisville. After dinner, cruise on down to the Big Four Bridge and head on up. As the sun goes down, you will be glad you visited this city.


Another Louisville favorite, The Homemade Ice Cream and Pie Kitchen has been slinging the best pies, cakes, ice cream, and cookies since 1982. You cannot pass this place up on your trip to Louisville. Try any of the delicious ice cream flavors, the best chocolate swirl cookies you have ever tasted, or go with house favorite, caramel cake. There are 10 locations, but for our purposes you will want to go to the Frankfort Ave location.

10:30 pm – THE SILVER DOLLAR – Bourbon

After dessert, a brief walk down Historic Frankfort Avenue will lead you to a funky spot in an age old firehouse that is reminiscent of a honky tonk. The Silver Dollar has an extensive selection of bourbons, and an upbeat atmosphere to keep you kicking. When you’re finished kicking, you can finally retreat to wherever it is that you call home in Louisville. I promise that after you take this tour, you won’t want to leave.

Thinking about moving to Louisville or relocating within Louisville? I would love to speak with you about your next home – – 502.509.9278

You can view all Louisville homes for sale at

View homes for sale on the go with my GPS enabled mobile app!



Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s