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    Sir Winston's

    3.9 (50 reviews)
    InexpensiveKaraoke, Cocktail Bars
    Open 10:00 am - 2:00 AM (Next day)

    Sir Winston's Photos

    Business Info

    SIR WINSTON'S ATMOSPHERE

    What's the vibe?
    Juke Box
    Moderate noise
    Casual
    Outdoor seating

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    Recommended Reviews - Sir Winston's

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    a neon sign for a restaurant
    TaKori H.

    I was invited to Sir Winston's last night and I'm so happy that I accepted the invitation. I had an absolutely amazing time. This place has a friendly and welcoming environment. It seems that most of the patrons are regulars because everyone knew each other. I've never met so many amazing people at once. I love that people came and conversed with me about topics that I care about and most people are afraid to discuss. My face and ears still hurting from laughing so much. Also, people I've never met bought me drinks and just made my night out so great. Again, the people I met were absolutely amazing. I can't wait to go again. Maybe, I'll perform a Tina Turner song for karaoke. Haha.

    Cynthia Garza
    Cynthia G.

    I went over there on Saturday on 15th, and it was so awesome! Love the drinks. I felt bad the bartender was working alone with no help on the waitress. I'm going on Friday or Saturday. I will keep practicing my singing. LOL Keep up the great work DJ & bartender! :) Cheers ! See you all soon. P.S. A Notary Public , just in case some one's needs one! LOL

    Sir Winston's daily drink specials.
    Dann K.

    $1 Thursday Nights 8 to 11pm, well Vodka and Lone Star & Miller Lite longnecks. I don't need to write any more, but I will. Awesome neighborhood bar. Great atmosphere, friendly staff, a/c that works (I can't believe I need to write that), karaoke, live bands, cold beer, $8 pizza (looks good, haven't tried it yet). Check this place out.

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    Page 2 of 2

    Ask the Community - Sir Winston's

    How much does cost to sing karaoke song?

    Pay to sing? Who pays to sing? I wouldn't think anyone pays to sing anywhere, including Sir Winston's; but, I guess I wouldn't know because I stay away from Kroak-a-oke as much as I can. (I'm a real musician.) I just can't imagine anyone charging to… 

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    Review Highlights - Sir Winston's

    Great atmosphere, friendly staff, a/c that works (I can't believe I need to write that), karaoke, live bands, cold beer, $8 pizza (looks good, haven't tried it yet).

    Mentioned in 2 reviews

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    RD Speakeasy - Exterior entrance

    RD Speakeasy

    4.7(80 reviews)
    0.7 miOak Park/Northwood
    $$

    Rd Hidden is one of my preferred destinations - whether meeting a close friend or enjoying a solo…read morevisit - to unwind with a well-deserved beverage while catching up on personal finances. On a recent visit, a best friend reserved a spot for us, and we ended up staying for an extended, thoroughly enjoyable time. Special thanks to Parker for the attentive service. Thanks, Parker, you are amazing. This remains one of my top hidden gems.

    Enjoyed my visit to the RD Speakeasy. It wasn't easy to find, but was worth the search! After I…read moremade the reservation online, I got the confirmation but not the password. So on the way, I texted and requested the password. After a brief search and knocking on several doors, I realized the entrance is behind the restaurant in its own small parking lot. Look for the green light and avoid searching around like a weirdo, like me lol. Once inside, I found the interior is cozy with seating for couples, small groups and bar seating. We asked the mixologist to put his own spin on old fashions and he delivered. I'm addicted to the spicy cinnamon version that he created! The quail pops were a nice little appetizer although they could have used a bit more seasoning. I think the drink and app prices were very reasonable. Service was laid back and friendly. My only reco would be to maybe put a bit more thought into the vintage decor and secret restroom. The restroom lock was hard to figure out, especially after a drink or two lol. Overall this Speakeasy is a great spot to add a bit of intrigue to your evening.

    Photos
    RD Speakeasy - Shrimp corn dogs and soft pretzel

    Shrimp corn dogs and soft pretzel

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    RD Speakeasy

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    The Modernist

    The Modernist

    4.6(235 reviews)
    5.4 miGovernment Hill
    $$

    The Modernist -- A True Speakeasy Experience in San Antonio…read more If you're in downtown San Antonio, take a break from the River Walk and check out The Modernist. This is a true speakeasy-style lounge that's easy to overlook from the outside--it looks like a regular, unassuming place. But once you step inside, the atmosphere completely changes. The interior is cozy, intimate, and has that hidden-gem feeling you want from a speakeasy. The staff members are incredibly friendly and welcoming, which made the experience even better. I had the pleasure of having Adan behind the bar, and this guy knows how to make a good drink! As always, I started with my go-to Old Fashioned. I have to say, it was easily one of my top two Old Fashioneds I've ever had. Then I told Adan to surprise me, and he came up with some kind of peanut butter chocolate martini. Let me just say... it was a true pleasure. Rich, smooth, and absolutely delicious. What I really liked about The Modernist is that it feels like a place the locals actually frequent rather than just another tourist spot. I genuinely had a great time here. If you're visiting San Antonio and find yourself downtown, give The Modernist a try. Step away from the River Walk for a little while--you might just discover your new favorite spot.

    My wife and I went to The Modernist after seeing it on social media. There wasn't a drink menu, and…read morewe were told the idea is that you tell the bartender what you like and they make something for you. Her first drink was a lavender-style cocktail and was fine. For her second drink, she told the bartender to surprise her. He gave her a look and asked more than once if she was sure she wanted him to surprise her. Instead of making her an actual cocktail, he poured her what seemed to be a straight, extremely bitter liqueur. The whole interaction felt sarcastic and like he was intentionally messing with her rather than trying to make her something she would enjoy. What bothered me most was the attitude behind it. We weren't being rude, demanding, or causing problems. We were there to have a good time and experience the whole "tell us what you like and we'll make you something" concept. I did call the number listed for the business afterward trying to speak to someone about it. The person who answered said I had the wrong number and didn't know what I was talking about. I got angry during that call and said some things I shouldn't have, and I can admit that. But that doesn't change how disappointing the experience at the bar was. We expected a creative and welcoming experience and instead left feeling like my wife had been mocked. I hope management sees this and addresses it, because the concept of the place is great, but the way we were treated completely ruined it for us

    Photos
    The Modernist - Weller 12 by way of Jason G! Thank you my friend!

    Weller 12 by way of Jason G! Thank you my friend!

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    The Modernist - The bar

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    The bar

    Sir Winston's - karaoke - Updated September 2026

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