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    The WineHouse

    4.7 (6 reviews)
    Closed 4:30 pm - 11:00 PM

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    Flight Wine & Bourbon Bar - Custom flight

    Flight Wine & Bourbon Bar

    4.8(6 reviews)
    3.7 mi

    I had such a good time here and was really impressed with how fun and relaxed the atmosphere was…read more My drink of choice usually involved bourbon so I was excited to try this place. The space feels cozy, and it was easy to settle in and enjoy the night. My friend and I loved checking out the different drink options, and the wine machines seem simple to use. The prices were a little high for me but I don't mind splurging occasionally. The whole place feels like a spot you could come to for a casual night out or something a little more special. I'd definitely come back to try some wines and explore the menu again.

    I was excited to try out Flight and wasn't disappointed at all! The inside is very cute and cozy…read moreand my friends and I found a nice spot with comfy armchairs to relax in. We ordered some food, including the beautiful and delicious charcuterie board and a couple flatbreads. I really like that there's a decent food menu including everything from $2 snacks to fuller meal options and desserts. Then we were onto our beverage choices. A couple of my friends opted for whiskey flights that they had been looking forward to sipping. And then a couple of us did the wine option. I didn't understand how it worked at first but it is very simple -- you get a little card to swipe at the wine machines and then you can choose whichever wine you want. You can opt for a small tasting pour or more of a traditional pour. At the end of the night you return your wine card and pay for whatever you had. I have heard of this type of wine bar before but hadn't tried it yet. It's brilliant! Everyone enjoyed their drinks and it was fun to try some new wines and whiskeys. I would definitely come back to enjoy the tots and some different wines next time!

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    Flight Wine & Bourbon Bar
    Flight Wine & Bourbon Bar
    Flight Wine & Bourbon Bar - The sangrias are incredible.

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    The sangrias are incredible.

    Cask & Ale

    Cask & Ale

    4.2(77 reviews)
    6.2 miCapitol
    $$

    Another first-time experience in Madison, and this spot came highly recommended if you're a true…read morewhiskey or bourbon lover, and wow it did NOT disappoint! It happened to be near the theatre we went to, so we decided to stop in and check it out. They have nearly 775 different types of whiskey to choose from, which is wild! I loved that they offer different ounce sizes so you can sample a few, and they even pair it with water so you stay hydrated while tasting (smart touch). Price ranges between ~$7.50-$20.00+. The place had a cozy, lounge-like vibe and was pretty busy, but the staff was friendly and helpful. It's first come first served for seating, just like any bar. We sampled a few whiskeys and also tried their premade espresso martini. The whiskey selection was phenomenal, the espresso martini was decent, not the best I've had (it was premade), but still enjoyable (it's made with Tito's, which isn't my favorite base, but I appreciate the fresh coffee beans they used). All in all, this place is a hidden gem. Great whiskey, friendly staff, and the perfect cozy spot to escape the rain for a while. I'll definitely be back next time to try even more from their list!

    The perfect chill spot for a couple, if you need a cozy booth with dim lighting & good cocktails…read morethis is it! We also loved that the football game was on and it wasn't too loud. It's intimate and the drinks are fire. We stuck with the classic old fashioned and felt they were strong and well crafted - thank you for a true luxardo cherry too! We ordered at the bar but chilled in a booth. So many whiskey options!!! Service is friendly & quick!

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    Cask & Ale
    Cask & Ale
    Cask & Ale

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    The WineHouse - cocktailbars - Updated July 2026

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