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    The WineHouse

    4.7 (6 reviews)
    Closed 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(431 reviews)
    6.0 miCapitol
    $$$

    The view here is absolutely beautiful, truly one of those places where you can sit, relax, and just…read moreenjoy the atmosphere for hours. Everything about the setting feels peaceful, scenic, and special. Whether you come during the day or around sunset, the surroundings make the entire experience even more memorable. The food was excellent and honestly one of the best we had in Wisconsin. Everything tasted fresh, flavorful, and high quality, and you can tell a lot of care goes into both the presentation and the ingredients. Every dish we ordered was delicious, and the menu had great options for everyone. The service was also outstanding. The staff was warm, attentive, professional, and genuinely welcoming from the moment we arrived. They made us feel very comfortable and took great care of us throughout the meal. Overall, this place has everything, amazing views, fantastic food, and wonderful service. Definitely one of the top spots we visited in Wisconsin, and a place we would happily come back to again. Highly recommend for both locals and visitors looking for a special dining experience.

    Had tapas and cocktails after our daughter's graduation. Couldn't have had a better celebration…read more Menu was thoughtful and the food was absolutely delicious. Service was top notch. Views of the capitol at night made our last night in Madison bittersweet. Highly recommend.

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    Eno Vino Downtown - The Pearfect Elyx-ir - delicious

    The Pearfect Elyx-ir - delicious

    Eno Vino Downtown - Annatto Pork Tacos

    Annatto Pork Tacos

    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 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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    Casetta Kitchen and Counter - Vegetalian on focaccia bread

    Casetta Kitchen and Counter

    4.6(180 reviews)
    6.0 miCapitol
    $$

    Casetta is one of the best places in Madison. The ingredients are freshly prepared and of the…read morehighest quality. They have a special sandwich every day and I strongly recommend getting it before they run out. Their focaccia is to die for!! Honestly so are their chocolate chip cookies. It's a small spot and gets super busy during lunch so I would expect a long wait that is extremely worth it. All of their employees are incredibly nice and passionate about their job. Shoutout Ella the cashier! She was so funny and gave me the best recommendations - give her a raise!

    Stopped by here for lunch on a weekday. I ordered the Paradigm sandwich. The flavor of the sandwich…read morefillings were really good, especially on the marinated bell peppers inside. The sandwich had a good variety of textures throughout - my only wish was that the focaccia was also toasted. I think that would complement the sandwich textures even more. The coveted chocolate chip is *that* good. Thin, crispy edges, chewy center with flat chocolate wafer chips. The salt on top was a wonderful contrast to the sweet chocolate. You also can't beat the price of $2.25 for a good cookie. My only other complaint would be the limited seating. The workers here also try to provide table service and bring your sandwich out to you if you do dine-in. However, there isn't a system for them to find you at the table easily and they are just wandering around looking for you by name. Having a little table # placard would benefit the staff here.

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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 May 2026

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