Kentucky · Travel

Louisville Weekend Guide | Bed & Breakfast + Itinerary

Louisville Weekend Guide | Bed & Breakfast + Itinerary

Louisville Weekend Guide

When I chose Louisville as one of my destinations, I had a lot of people ask me… why Kentucky? What is there to do there? Um, well let me be the first to tell you… TONS! I spent 3 nights exploring the Louisville area and we went non-stop the entire time. So I want to make sure that I send a special thank you to The Louisville Tourism Department for helping me put this itinerary together. I hope you enjoy my Louisville Weekend Guide:

Louisville Weekend Guide | Bed & Breakfast + Itinerary

The Itinerary:

Day 1:

  • 3 pm Check-in at Chateau Bourbon (B&B)
  • 5 pm complimentary Happy Hour at Chateau Bourbon
  • 7 pm Drinks at Commonwealth Tap (walking distance)
  • 8 pm Dinner at 502 Bar and Bistro (walking distance)

Day 2:

  • 9 am complimentary breakfast at Chateau Bourbon
  •  11 am depart for Huber’s Winery & Orchard (around a 30-minute drive or Uber across the river and into Indiana, and well worth it)
  • All day: Wine Tasting, Tour, Lunch, Shopping, Fruit Picking, etc. at Huber’s Winery
  •  Return at leisure to Chateau Bourbon for rest or nearby shopping
  • 7 pm dinner at Volare

Day 3:

  • 9 am complimentary breakfast at Chateau Bourbon
  • Explore at leisure
  • 12 pm lunch at Proof on Main (downtown)
  • 1:30 pm Tour of Evan Williams (walking distance downtown from Proof on Main)
  • Explore downtown at leisure
  • 4 pm Kentucky Derby Museum (attached to Churchill Downs Horse Track)
  • 5 pm Attend a live race at Churchill Downs
  • 8 pm Dinner at Bourbons Bistro

Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0148Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0194DSC_0143Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0139DSC_0137DSC_0136Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0129-2DSC_0128-2


The Bed and Breakfast:

Chateau Bourbon

If you actually took the time to look at all of the beautiful photos above this paragraph, then you should already be in love with the gorgeous Chateau Bourbon Bed & Breakfast. Located in Prospect, KY (right outside of the city), sits your perfect home away from home. Owners Missy and John put their heart and soul into Chateau Bourbon and it simply oozes out in every inch of the immaculate property.

All guests of Chateau Bourbon are invited to indulge in a complimentary top-notch 3-course breakfast each morning, as well as a complimentary house-made happy hour drink and dessert each evening at 5 pm. And I highly recommend being in attendance for both as much as possible!

Chateau Bourbon offers four guest rooms and even an option to rent the entire house for large groups. However, my personal favorite feature of Chateau Bourbon is the gorgeous front porch and back patio. If you look back through the photos you will see the giant hanging swing on the front porch and the adorable individual swings on the back patio. I spent 92% of my time at the house in these areas! My Louisville Weekend Guide wouldn’t be complete without a stay at Chateau Bourbon.

DSC_0223Louisville Weekend Guide | Bed & Breakfast + ItineraryIMG_8522Louisville Weekend Guide | Bed & Breakfast + Itinerary

Commonwealth Tap:

Chateau Bourbon is located in a neighborhood called Norton Commons; alongside it are a variety of restaurants, shops, and other businesses within walking distance. Commonwealth Tap is a beautiful wine, craft beer, and bourbon bar located just steps away from Chateau Bourbon. With a gorgeous outdoor seating area and a sliding garage-style door in the front, the atmosphere itself is overwhelmingly appealing.

We sat outside and split an exquisite bottle of Moet 2012 Grand Vintage Rose’. It was the perfect way to start our first evening in town! Kenny (partner and GM) greeted us with a friendly welcome; it was clear that he truly loved his business and I couldn’t be more excited to share it with you! Commonwealth Tap is also known for their famous wine and bourbon slushies, so definitely keep that in mind when you visit.

DSC_0244DSC_0245Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0249DSC_0250DSC_0251DSC_0252DSC_0256DSC_0241

502 Bar & Bistro:


Course 1

  • -Calamari – miso aioli & sweet chili jam*****
  • -Korean style short ribs – ramp pesto, scallions*****
  • Freedom Run Farm lamb meatballs – cucumber & tomato salad, whipped goat cheese***

Course 2

  • Ashbourne farms dinosaur kale salad – charred carrots, peanuts, oranges, ginger soy vinaigrette*****

Course 3

  • ramp cavatelli – charred pickled ramps, ramp pesto, sugar snap peas, pecorino romano*****
  • mac & cheese gratin – cavatappi, Jarlsberg, black truffle cheddar, Tillamook cheddar*****

Course 4

  • Joyce farms chicken – beet gnocchi, charred carrots, ramp pesto, black truffle vinaigrette***
  • Berkshire pork chop – blackberry maple glaze, succotash, smoked gouda grits***


  • hand painted chocolates****
  • key lime “pie” – white chocolate mousse, lime curd, brown butter cumin blondie***
  • corn cookie with blueberry maple ice cream and salted corn nuts**

*stars indicate my favorites on a scale from 1-5

Mom and I were both blown away with everything about The 502 Bistro and Bar. From the atmosphere to the service, and most importantly the delicious uniqueness of each and every hand-crafted dish that was prepared for us! Chef Ming was an excellent host and did not disappoint in the kitchen! If I ever end up in Louisville again (which I hope I can attend the Kentucky Derby next year), I will 100% be back to dine at 502! I am a huge calamari fan, and chef Ming’s calamari and house-made sauce were both to die for. Also, it is located just steps from Chateau Bourbon!

DSC_0264DSC_0263DSC_0272Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0282Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0289DSC_0293DSC_0307DSC_0308DSC_0309Louisville Weekend Guide | Bed & Breakfast + Itinerary

Huber’s Orchard, Winery & Vineyards:

Huber’s Winery is Indiana’s largest tourist attraction. With over 800 acres of grapes, fruits, and vegetables… there is something for everyone! Huber’s Winery is located just across the river (around a 30-minute drive from Louisville), and it is well worth the drive or Uber.

Family owned and operated, the Huber Farm was created in 1843 and the Huber family hasn’t stopped since. We got to meet several of the Huber’s, each of which was hard at work. Their passion is very clearly shown in both their facilities and their products. Huber’s offers U-pick fruits and vegetables, a fabulous winery, restaurant, starlight distillery, an ice cream shop, and a fresh market store. Their hand-crafted pizzas, blackberry whiskey, and fresh strawberries are just a few of the stand-out reasons to stop in for a visit.

DSC_0310Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0320DSC_0322DSC_0333DSC_0334DSC_0329




  • Prince Edward Island Mussels – Sautéed p.e.i. mussels with prosciutto, cremini mushrooms, and peppadews finished in white wine and roasted garlic cream**
  • paired with the Brooklyn cocktail – Barrel-Aged Maker’s Mark, Averna Amaro, Contratto Bianco Vermouth, Luxardo Maraschino Liqueur**


  • Kale Salad – Baby Blue Kale Chiffonade, toasted walnuts, red onions, roasted red peppers, crispy pancetta lardons, and grated pecorino Romano cheese tossed in a stone-ground vinaigrette*****
  • paired with Sonoma-Cutrer Russian River Ranches 2016, Sonoma, Ca*****


  • Pappardelle Boscaiola – House-made Pappardelle pasta tossed with mushrooms and bacon tossed In demi-glace cream sauce*****
  • paired with Quilt Cabernet 2016, Napa Valley, Ca****


  • Sea Bass – Pan Seared Chilean Sea Bass finished with a sauce of ratatouille 
  • paired with Ruffino Orvieto Classico 2016 DOC, Umbria, Italy****


  • Vitello SaltimboccaVeal scaloppini sautéed with prosciutto, sage, and mozzarella finished with a white wine and butter sauce, accompanied with a pepperoncini and Kenny’s Kentucky Moon Swiss Cheese*****
  • paired with Mer Soleil Pinot Noir 2017, Santa Lucia Highlands, Ca*****


  • Tiramisu – Lady Fingers soaked in espresso, Frangelico, and Kahlua, layered with a  sweet mascarpone cream****
  • Sea Urchin Ice Cream****
  • Volare’s Lemoncello***

*stars indicate my favorites on a scale from 1-5

Volare is an upscale Italian restaurant with amazing flair and an even more amazing chef. Executive Chef Joshua Moore is not only a former winner of the show Chopped but also creates dishes for Volare using his own garden. Alongside him, general manager Jonathan Tarullo runs the front of the restaurant with a great presence and hospitality.

Every single dish that was put in front of us was outstanding, but there was something extra special about the kale salad. What was it? The kale was freshly picked that morning from the chef’s garden. This was hands-down the best salad I have ever experienced, and I am not even a huge fan of kale. With all of this said, a trip to Louisville without a meal at Volare would be a huge disappointment.

Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0348Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0356DSC_0363Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0359DSC_0368DSC_0346

Proof On Main:



  • Chateau de Roquefort Corail, 2018 Cotes de Provence****


  • Spring Onion Soup – Cabbage, jam, pepita, chili oil**
  • Grilled Chicken & Romaine Salad – Sundried tomato walnut pesto, pangrattato, creamy parmesan, anchovy*****
  • Spicy Chicken Sandwich – Red Chile, Bread & Butter Pickles, Iceberg****

*stars indicate my favorites on a scale from 1-5

Proof on Main is an up-scale, artsy eatery located in the 21C Hotel in downtown Louisville. As you can see from the photos above, each piece of art and furniture makes a bold statement for the restaurant. This makes the vibe an uplifting and intriguing place to relax for lunch or dinner (and to get a great new Instagram shot while you’re there). We enjoyed a fabulous lunch at Proof on Main, and my absolute favorite dish was their fresh caesar salad.

DSC_0370DSC_0375DSC_0390Louisville Weekend Guide | Bed & Breakfast + Itinerary

Evan Williams Bourbon Experience:

The Evan Williams Bourbon Experience is located just steps from Proof on Main in downtown Louisville. The experience takes you through the story of who Evan Williams is and why the company who actually makes Evan Williams Bourbon (Heaven Hill) chose to dedicate this bourbon to his name. Throughout the tour, we got to taste one of their whiskeys straight out of the barrel. Later in the tour, we sat down at tables and were told to open the secret compartment. This compartment opened and out came our bourbon tasting flight. The Evan Williams Bourbon Experience was truly an informative and interesting tour. The history and flavor combined makes it a must-do in this Louisville Weekend Guide.

Louisville Weekend Guide | Bed & Breakfast + ItineraryLouisville Weekend Guide | Bed & Breakfast + ItineraryLouisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0434

Churchill Downs:

Nothing is more iconic in Louisville than Churchill Downs. I was thrilled that there was going to be live races while we were in town. I tried my luck a few times betting on around 5 of the 8 races, and I actually surprised myself! There are tons of factors to consider and I am no expert by any means, but it is an extremely interesting and fun way to spend an evening.

The grounds and stands are absolutely stunning. I am 100% ready to come back to another race one day; I’d LOVE to be able to go to the Kentucky Derby next year. I think it goes without saying, but Churchill Downs should be your #1 destination in your own Louisville Weekend Guide.

DSC_0461Louisville Weekend Guide | Bed & Breakfast + ItineraryDSC_0462DSC_0463DSC_0469DSC_0468

Bourbon’s Bistro:

The Menu:

Course 1:

  • Buffalo Wings****

Course 2:

  • Filet of Beef – pan seared, sage herb butter, fingerling potatoes, asparagus, balsamic glaze****
  • Cacio e Pepefresh Campanelle pasta, baby spinach, Parmesan cheese, cracked pepper, grilled and blackened heirloom cauliflower, white truffle oil****

*stars indicate my favorites on a scale from 1-5

Bourbon’s Bistro is actually located right across the street from Volare (another restaurant that I have featured in this article). They have done an excellent job of mixing an upscale vibe with a casual, cool setting. The menu has a wide variety of options; there is definitely something for everyone. We actually sat outside on their side patio, which I adored. Both entree dishes that we were able to taste were outstanding. The steak was cooked to perfection and the pasta was marvelously blended with truffle oil and parmesan.

Louisville Weekend Guide | Bed & Breakfast + ItineraryLouisville Weekend Guide | Bed & Breakfast + Itinerary

This was most certainly an action-packed trip. However, I wouldn’t have had it any other way. Plus, coming back home to Chateau Bourbon every evening truly felt like home. I could not recommend a weekend in Lousiville more, and thank you for reading my Louisville Weekend Guide.

One of my main goals with Wine and Weekends this year is to inspire people to break their vacation time into more mini-trips, instead of 1-2 big (often repetitive) trips. The world is such a beautiful place; I promise you won’t miss your “usual” spot too much if you decide to give a few new places a try!

I’m home this week to get a lot of work done, rest, and re-group for lots of fun things coming up! Stay tuned and thanks for reading and supporting. Follow along on Instagram (@katie.wineandweekends) for more content and to get to know me more behind the scenes 🙂

Previous Post: Gordonsville’s Famous Fried Chicken Festival

Until next time,


Katie Church signature

Leave a Reply