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    Cask & Ale

    3.9 (145 reviews)
    Open 3:00 pm - 2:00 am (Next day)

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    CASK & ALE ATMOSPHERE

    What's the vibe?
    Live music
    Casual
    Trendy
    Intimate

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    Recommended Reviews - Cask & Ale

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    Sh*ts Bananas
    Melissa E.

    Stopped in on Tuesday night while exploring Downtown for an amazing drink. The staff was quick to recommend their favorites and also without being asked gave us water cups (and kept them full!). I ordered the sh*ts bananas and my friend ordered the Chai Hard, both were amazing. I would definitely recommend for a quick drink or to hang out for while since their bar area and chairs are so comfortable!

    Margarita
    Mary L.

    We stopped by Cask & Ale on a Monday evening primarily for drinks, and it turned out to be a perfect, laid-back experience. There were only a few other people in the restaurant, which made for a relaxed and pleasant atmosphere--ideal for unwinding. The focus here is definitely on the spirits, and their happy hour is fantastic. At just $8 per cocktail, it offers exceptional value. We sampled two classics: the Margarita and the Old Fashioned. The quality of the drinks was ok. My Margarita was particularly strong--they certainly don't skimp on the alcohol here! If you appreciate a cocktail that packs a punch, you will be very satisfied. The Old Fashioned was equally well-made.

    Tacos
    Michael D.

    Cask & Ale was a total surprise during a recent trip to Sarasota with my partner. We had the best experience! The food was beyond good. The Sicilian rice ball was phenomenal! We also had the tacos, ceviche, Philly cheesesteak eggrolls, espresso martinis and a few other options. Their happy hour is the best anywhere! Full sized plates for $7 each! The staff is friendly and the bar is beautiful. I can't recommend this place enough if you're in the area or on Main Street!

    Nachos
    Rickey C.

    A++ spot. Great vibe. Really nice space. Excellent food. Great beer and cocktail list. Service was top notch and super friendly. Definitely a go-to spot

    Bartender climbing the ladder to the lockers!
    Susanne B.

    Had a great time at Cask & Ale last week! We stopped for a pre dinner drink but when the rain started we decided to stay! Alejandro was our bartender (and he looks like he could be Matthew MCConaughey's son!) who made great drinks for us and explained about the lockers behind the bar. Really cool place and the food was good too!

    1548 salad with chicken! Good!
    Amy M.

    Fun atmosphere, good service and food was good. We went for happy hour and will be back! We got the 1548 salad with chicken (regular shredded cheese instead of blue cheese) and 3 tacos (steak, brisket & shredded pork). Good and wanting to try different things!

    Sydney W.

    We got to see two different sides of Cask & Ale. We got there when they opened, and Jacob was an amazing bartender. Conversational, super friendly, and made us want to go back. We got mimosas and loaded fries..yum! We then saw the nightlife for a Friday, and wow! A true bar vibe, great music and drinks!!

    Angela C.

    The food was good. Our waitress was an ass, because she knew my son and he wasn't drinking to begin with, but she had to be nosy and ID me just to see who he was with and how old I was . I just look good sweetie. Martini was good. I've been there a few times with friends and the place is always fun.

    Pumpkin Martini
    Ahra J.

    We came to visit here while we were in town for a wedding. It's one of the few bars that were packed. When we visited, it was early November and they had a great pumpkin martini that I really liked. They have your normal selection of beers and some specialty cocktails on the menu. The place got crowded fast both nights we visited and one night a fight broke out, but security was quick to resolve and get them out. The prices are pretty comparable to other bars and coming from the DC area, I would even say they were cheaper. While the space is big, I will say a lot of the table tops got taken fast so be prepared to stand if you're going there later. There are 2 single stall bathrooms in the back so the line does get long as well.

    a bar with a chalk board

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    1 year ago

    So loud. So obnoxious. A night that includes Cask & Ale is going to include a raging headache in the morning.

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    6 months ago

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    3 years ago

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    2 years ago

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    1 year ago

    Great place! Very good bar service and cocktails! Live music some days with an open air feel!

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    8 months ago

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    2 years ago

    Good Times but very loud at times very crowded. Got to get there early if you want to get a table otherwise standing room only.

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    4 years ago

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    2 years ago

    This spot is excellent for a date night out! Live music was excellent and bartenders wonderful drinks. Would definitely recommend!

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    State Street Eating House + Cocktails

    State Street Eating House + Cocktails

    4.0
    (297 reviews)
    0.0 mi
    $$

    Took a group of friends visiting from Jax for a girls' night out and definitely picked the right…read moreplace. Food: delicious and creative. Every one of the five different entrees merits the five-star rating. Service: exceptional. Our server, Mr. Lenza, was beyond what even the most demanding of customer could want. Engaging, knowledgeable (about many, many things that extended beyond entree questions), fun, and attentive (but not overly so; he hit the perfect mark). Ambiance: upscale-fun meets modern-artisan. Bonus was meeting one of the owners who entertained us with hidden "duck" tales [lol; intrigue intended]. This will be my go-to spot for guests in the future (as well as for me when I'm craving creative & tasty cuisine). Well done, SSEH, well done (& I'm not just talking how to prep my burger )!

    Our group booked brunch here for 2 groups during a wedding weekend and wow, this is the spot! They…read moresat us in a cool little private room tucked in the back. The cocktail variety was top notch and all the food was delicious. Our group enjoyed the avocado toast with the whole wheat sourdough, noting the bread was so good. We also had the pork sandwich and naked burger. All solid choices. The specialty that day was biscuits and gravy with the most amazing gravy with a little spice. Our server Kristy was so lovely and took care of us so much. I would definitely recommend checking this out for Brunch and it looks like they have some great Lunch and Dinner options. The little outdoor patio would be great for nice weather.

    Photos
    State Street Eating House + Cocktails
    State Street Eating House + Cocktails
    State Street Eating House + Cocktails

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    The Doctor’s Office

    The Doctor’s Office

    3.9
    (290 reviews)
    16.0 mi
    $$$

    5 Star update- same great craft cocktails but adding that they have wonderful outdoor seating and…read moresome lovely dishes. We grabbed reservations for the outdoor area to enjoy the weather and were thankful for the shady tree cover. This time we opted for some bites and though the menus change seasonally, I would recommend anything featuring tomatoes. They use truly fantastic heirloom tomatoes that remind you what you're missing with the watery ones we get at the grocery store. Also recommend the Mediterranean Platter. It's full of veggies and the dips are YUM. As usual, the cocktails didn't disappoint. It's never a weekend in AMI without a visit here! Previous Review: 5 Stars for the best cocktails on AMI, and a craft cocktail bar vibe you wouldn't necessarily expect here. (Plus, the service is AMAZING) We walked in (no reservation) after dinner one weekend evening and we were greeted by Matt, who found us a spot at the bar. He gave us menus and a "wellness shot" -- delicious little concoction to wet your palate! Right away I was blown away by the interior and the menu. This looked like it belonged somewhere in Denver or Chicago, but I was thrilled to find it on the island! Matt helped guide us to drinks we'd like on the menu. I ordered the Purgatory, made up of Bourbon, chocolate bitters, agave and premium mezcal. It was divine!! We also ordered some warmed olives, and they were hot and so fragrant. Definitely something I'd order again at the bar. I was stoked to see they have a veggie-specific section on the food menu and can't wait to go back for dinner. I'll definitely make a reservation though, as it was pretty full. Next time, in terms of drinks, I have my eyes on the espresso martini (off menu, but saw a pic on Yelp), and the kiss kiss bang bang. Thanks to Matt and Emily who helped us with our drinks along the way. Sometimes these fabulous craft bars can be pretentious, but the service here was a huge standout. Can't wait to return!

    Have been wanting to go to this place for years and finally went and unfortunately it was…read moreunderwhelming. I feel like the drinks used to be a lot more creative from what I saw on their socials and from what my friend said who went back in the day it used to be more of a speakeasy elevated cocktail vibe versus a tiki/dive bar vibe. We had to ask for the chips that are supposed to be given complimentary and then we ordered bread and soup which literally took an unnecessary like 30 mins or more to come out as we watched the people on both sides of us get their full meals before us when we got items that just had to be reheated. The tomato soup was very good once it finally came out, the rolls were good but nothing as great as the hype in my opinion for the menu. The drinks were good but honestly the starter shot given at the bar was my favorite which was a hibiscus Pom margarita which I ended up getting fully as my second drink. Service started out hot but then went downhill but that is unfortunately the standard of when gratuity is already included in a check. Then when it came time to pay it got weird when there was a simple mix up when my friend intentionally overpaid even with gratuity involved in her check and the bartender asked her if she wanted change and she said yes but never brought it back. My friend gave 3 - 20s on a $38 check (gratuity) already in but she wanted to tip a few more dollars because she is a very generous person and then when she asked about her change that's when it got weird and the bartender made it seem like she didn't understand why she wanted change instead of just apologizing for the mistake and they went back and forth for a few minutes with the bartender ending up just giving her the extra $20 back. Just left a weird taste in our mouths for the experience when I feel like any bartender would understand what she wanted to do with giving extra larger bills to split especially when she said she wanted change and it was a massive overpayment or if the thought there was a very generous tip like 30% would make sure with guest that's what they want and show appreciation if that were the case. It was just weird how it all was handled. The decor was on point for Christmas and the vibe was very casual but oldie vibes which makes sense for it being in Anna Maria island.

    Photos
    Dude who stayed too long
    Dude who stayed too long
    Praline Alexandra with homemade ice cream!
    Praline Alexandra with homemade ice cream!
    Old fashioned, cinnamon stick that looks like a cigarette

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    Old fashioned, cinnamon stick that looks like a cigarette
    Wink Wink Food & Drink

    Wink Wink Food & Drink

    4.3
    (54 reviews)
    0.5 mi

    What an absolute gem of a restaurant. The ambiance is artsy, whimsical, fun--and it all just works…read more Really well. Our server, Juliana, provided absolute perfection. She was bright, effervescent, eager to please, extremely knowledgeable about every drink and food item on the menu, always present when needed but never hovering. She has perfected her craft and it made for a wonderful experience. The menu is written with flair and verve, and every offering seems irresistible. We wanted to try everything, but of course couldn't, so we made do with a couple of their signature cocktails (wonderful), a flatbread appetizer (also wonderful) and the very delicious meat loaf and the gemelli pasta entrees. I 10 out of 10 in every respect. We were quite concerned that we were the only patrons in the restaurant during our entire meal. It was early on a Tuesday evening in low season, but still. I hope more folks discover Wink Wink as it would be a shame to lose such a treasure. I would think they might want to consider offering a happy hour to boost things a bit. On the other hand, they could be doing very well and we just hit an off night. Go. Try it. The whole experience will be very entertaining with the art and whimsy of the decor and the menu. Great vibes. and the service and food were wonderful.

    There's a floral pop up event of some sort going on The food…read morewas great! And the drinks were unique and tasted even better! The charcuterie was like a dream, and the Popsicle champagne drink wasn't too shabby! The service was good, and it wasn't too busy when I went. There's definitely photo ops for days for all my fellow content creators! The manger was friendly as well, and was nice enough to check in on all the guests here and there. Will def come back soon!

    Photos
    Inside restaurant
    Inside restaurant
    Pickled Eggs
    Pickled Eggs
    Deviled eggs

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    Deviled eggs

    Cask & Ale - newamerican - Updated July 2026

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