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    The WineHouse

    4.7 (7 reviews)
    Open • 4:30 pm - 9:00 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.

    Eno Vino Downtown - Crispy Lobster

    Eno Vino Downtown

    4.1(437 reviews)
    6.0 mi•Capitol
    •$$$

    I genuinely think I'm nicer than the average tipper, so I try to be understanding when things don't…read morego perfectly. It took about 20 minutes for us to be greeted by our server. Fair enough, I can forgive a single mistake. Once we were greeted, our server seemed to realize that, for as nice of a place as this was, the wait while the restaurant wasn't busy (there was maybe five tables sat) really wasn't acceptable, so we were given a complimentary drink. After ordering bruschetta and a cheese board, I expected things to move a little quicker since they were two fairly simple appetizers. Our bruschetta and espresso martini arrived, and both were delicious and well worth the price; no complaints there. Unfortunately, our cheese board was forgotten. Since it was obviously missed, our very kind server offered us a complimentary espresso martini which was second complimentary beverage, which was delicious. Recognizing that the overall service had been subpar, our server also offered us a free dessert. We were given the crème brûlée, which was just okay and a little too sweet for my taste and also cold. All in all, considering how slow the service was despite there being very few tables, there were more delays and mistakes than there should have been. That said, our server did a good job of making up for it with the complimentary drinks and dessert. Overall, the food was decent and the view was great. I would come back for cocktails and appetizers, but probably not for a full meal. We still tipped well higher than average because our server was extremely apologetic for the sub-par service, and made up for it in comped orders. I expect better for the cost but appreciate the honesty with the service.

    We had a great experience dining at Eno Vino Downtown last Saturday evening. The service from Abby…read morewas simply amazing, and it made the whole evening event so pleasant. We went there to celebrate the 50th birthday of a friend from New York who was in town for the art fair. Abby was attentive, with good recommendations. She's such a sweetheart. We really had a wonderful time chatting with each other and eating the great food. The mocktails were excellent, and we decided on 2 sets of their special - a two-to-tango meal. The dishes were very generously served and delicious. I would highly recommend Eno Vino Downtown for any celebration.

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    Eno Vino Downtown - The Pearfect Elyx-ir - delicious

    The Pearfect Elyx-ir - delicious

    Eno Vino Downtown - Grilled lettuce - something new for me.

    Grilled lettuce - something new for me.

    Eno Vino Downtown - View from the restaurant

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    View from the restaurant

    Cask & Ale

    Cask & Ale

    4.2(77 reviews)
    6.2 mi•Capitol
    •$$

    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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    Casetta Kitchen and Counter - Vegetalian on focaccia bread

    Casetta Kitchen and Counter

    4.6(189 reviews)
    6.0 mi•Capitol, Downtown
    •$$

    Casetta Kitchen & Counter was exactly what I needed after a night out in Madison! I was visiting…read morefrom out of town and wanted something quick, easy, and delicious, so I searched Yelp and stumbled across Casetta. I'm so glad I did. I ordered the Italian sandwich, and it absolutely hit the spot. It was fresh, flavorful, loaded with quality ingredients, and honestly cured my hangover. Sometimes all you need is a really good sandwich, and Casetta delivered. The experience was made even better by the woman at the register. She was so sweet, welcoming, and genuinely friendly. Her kindness made the visit feel even more memorable and was the perfect start to my day. If you're visiting Madison or you're a local looking for an amazing lunch, I can't recommend Casetta Kitchen & Counter enough. Great food, quick service, and wonderful hospitality. I'll definitely be back the next time I'm in town!

    Casetta is one of those places where the food definitely lives up to the hype. The bread was fresh,…read moreimpressive, and probably one of the highlights of the meal. Everything tasted fresh and delicious. The atmosphere has an industrial-rustic feel, but the large kitchen right in the center of the space really makes it stand out. You can see a lot of the action happening while you wait, which adds to the experience. Service is quick and operates more like fast food: you order at the counter, then they bring your food out to your table. Just be prepared for a potentially long line depending on what time you go. As for the price, I'm not sure my particular order felt fully worth it. That said, I think I may have made the wrong choice. If I had gone with one of their more adventurous sandwiches, I probably would have felt like it was worth the challenge of dealing with Madison Street parking. Overall, Casetta is definitely worth trying. Everything is fresh, the bread is excellent, and I'd go back to give one of their more interesting sandwiches a shot.

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    Casetta Kitchen and Counter
    Casetta Kitchen and Counter - Paradigm on focaccia bread

    Paradigm on focaccia bread

    Casetta Kitchen and Counter - Exterior

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    Exterior

    The WineHouse - cocktailbars - Updated September 2026

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