For a Pre-Show Nibble
4-7 p.m. daily
Close to downtown Sarasota’s theatrical venues, Louies Modern draws an arty crowd looking to get in a mini-meal and share some spirits during the narrow window between work and the curtain rising. The energy crackles and the mix expands on Thursdays, when a boisterous crowd shows up for half-price bourbon and $2 flutes of champagne; and it turns downright manic on the weekends, when beautiful young people crowd the metal bartop and guard their low-backed seats. The duck tacos, touched up with figs and crème fraiche, are a hit, and the salty, spicy chicharrones, which crinkle when you drizzle lime juice over them, keep diners ordering round after round.
For Supper Club Chic
5-6 p.m. daily
Veronica Fish & Oyster bills itself as a throwback to the supper clubs of days gone by—and that’s the vibe you get when you walk through the restaurant’s doors, from the murals on the wall and marble-topped bar to shelves lined with books and tasteful knickknacks. Add upholstered chairs and banquettes and you feel like you’re in a vintage living room—a sublime setting for sipping cocktails. Veronica’s happy hour makes that exercise even more sublime, with $5 beer and wine specials, $6 cocktails and $7 small plates, including grilled oysters (yes, please—Veronica has a fantastic oyster bar), shrimp and scallop ceviche and smoked fish toast. Bourbon lovers must not miss the Empress of India, made with Old Forester bourbon, blackberry, vanilla and star anise.
For When You’re Craving ’Cue
2-7 p.m. daily
Brick’s is the new kid on the block—the block being red-hot State Street—and its happy hour is an excellent addition to the local scene. From 2 to 7 p.m., you can get beer, wine and cocktails for $3-$8, and small plates from $3 to $5. Our picks: the excellent house margarita ($5) and the chicken “chick”-arones, a play on traditional pork chicharrones that taste like the best chicken nuggets you’ve ever had. (The avocado and shrimp ceviche and the pulled pork nachos are also winners.) On most evenings, Brick’s throws open its floor-to-ceiling glass doors, and the thrum of downtown Sarasota nightlife, combined with Brick’s industrial-chic décor and twinkling café lights, makes you feel lucky to be exactly where you are at that moment—especially with that margarita and those chicken bites.
For the Downtown Biz Crowd
4-7 p.m. Monday-Friday
Youngish attorneys, brokers and bankers flock to downtown’s Cask & Ale, the men in loosened ties and rolled-up shirtsleeves and women subbing slip-ons for workday heels. They come for impressive deals on the beer and wine, plus happy hour-specific concoctions like the lemongrass-cucumber Collins, a sugary, herbal delight. Even non-drinkers stop in for the food— a mix of snacks and starters from 4 to 5 p.m. and the full menu after 5. A plate of poutine delivers a black pepper kiss, while the steamed bun enfolds a long, thick hunk of sweet ‘n’ smoky pork belly. On a recent evening, a pregnant woman sipped a mocktail while holding forth on the ocean’s worth of raw makimono she plans to order after she gives birth.
For Booze and Blues
5-7 p.m. Monday-Friday
A small James Brown figurine—an appropriate guardian angel—perches above the bar at the Blue Rooster. The Godfather of Soul surveys a spacious, high-ceilinged room, where the tables near the stage are often moved aside to allow revelers to swing and twerk to blues and R&B. Blue Rooster’s happy hour precedes the live music, which usually begins around 7:30 p.m., but in-the-know music fans like to pop in around 6:30 to take advantage of the restaurant’s deals before the band starts cooking. The restaurant’s owners also own Bradenton’s Darwin Brewing Co., so expect a choice pick of $4 Darwin drafts, with two taps set aside for seasonal beers-of-the-month. A Darwin Summadayze IPA tastes mighty fine next to a $3 plate of lightly fried black-eyed peas—crispy, crunchy and with a vinegary kick.
For the Ultimate End-of-Day Wind Down
4-6:30 p.m. daily
The Table Creekside has garnered a fanatical local following thanks to its house-infused liquors, creative menu and dreamy location right on Phillippi Creek. Happy hour offers all that as well, but at a fraction of the price. Get there early—the bar fills up fast—so you can grab a table overlooking the water, and order any of the $5 cocktail and tapas options, which are a total steal for the quality. Try the salty sea bass fritters with Key lime aioli, or the short rib Rangoon, a fun twist on the classic crab Rangoon that’s served with a kicky wasabi aioli. Wash them down with a Ginger Pear Blossom, mixed with house-infused ginger-pear vodka, pear nectar, velvet falernum (a sweet syrup made with an infusion of spices) and fresh lime. Meanwhile, watch kayakers and the occasional manatee glide by outside. Talk about the perfect way to end a work day.
For Civic Networking
5-7 p.m. Monday-Saturday
Three decades in, Michael’s remains the go-to spot for power players, whether they’re pow-wowing about how to make a difference over dinner or at lunch. We’ve seen some major brainpower coming together at happy hour, too—including a women’s group recently planning an ambitious fall calendar over $6 drink specials. Those specials include craft cocktails, beer and Michael’s Wine Cellar’s private-label wines. And because it’s Michael’s, the food is on point. Make a mini-meal out of the black pepper beef carpaccio rolls with shaved Parmesan, black pepper oil and chives, and sip on the herbaceous Michael’s Garden, named after proprietor Michael Klauber and made with vodka, honey, basil, rosemary and lemon. A drink and a snack while you change the world, and you’re home before 7:30 p.m.? That’s networking we like.
For a Midday Staycation
11:30 a.m.-5 p.m. Monday-Friday out of season, 2-4 p.m. Monday-Friday in season
Our pittance of beachfront drinking institutions remains a regional disgrace, but Beach House’s early-afternoon happy hour makes up for the lack of options elsewhere. Available only at its indoor and outdoor bars, the daytime discount menu includes two-for-one specials on sand-between-your-toes drinks (margaritas, piña coladas, Daiquiris), while the food menu provides portions big enough to soak up all that rum and tequila. On the beachside deck, young women wearing bikinis beneath their cover-ups clink glasses of white wine and scarf down plump peel-and-eat shrimp and softshell crab sliders slathered with Sriracha mayonnaise. At the bar, couples who snuck away from work smooch with lips salty from the rims of margarita glasses. After a summer of hurricanes, you may wonder, why do we keep living in such a precarious place? Happy hour on the beach answers the question.
For Hanging with the Cool Kids
5-7 p.m. daily
Social has been a go-to for downtown’s glitterati since it opened in 2013, thanks to its First Street location and sleek urban décor. The sofas on the outdoor patio are the place to be during the cooler months. Its “Social Hour” is a favorite for the after-work crowd, and the craft cocktails and Italian-inflected bites make for the perfect early-evening nosh. The drink and small plate deal lets you pick an appetizer (try the wood-fired pizza with prosciutto, goat cheese, mozzarella, garlic, tomato, basil and arugula) and a drink (order the White Negroni, made with gin, rhubarb, Carpano Bianco and orange zest) for $13. You can also order $5 craft draft beers, $6 wine and cocktails, and $7 snacks. Then sit back, and people-watch to your heart’s content as the sun sets over downtown.
For a Romantic Interlude
4-7 p.m. daily
With dim lighting, a quiet-storm soundtrack and a select pick of whiskeys, Libby’s and its adjacent LBar make an ideal destination for a discreet early-evening canoodle. Happy hour runs 4-7 p.m. every day of the week, with discounts on pretty much everything, including specialty cocktails, which retail for $10 but sell for $7 before 7. Try the signature old fashioned, built around Kentucky-crafted Larceny bourbon infused with brown butter and accented with chocolate bitters and orange oil. The food deals are equally impressive: Korean-spiced chicken in lettuce cups is a $6 treat, while the “bratty kid cheeseburger,” also $6, is big enough for dinner. We watched a sun-reddened couple soak up the air conditioning while killing a bottle of bubbly with the deeply satisfied look of people who didn’t plan to go anywhere anytime soon.
Editor's note, July 2018: Libby's Cafe + Bar is currently closed for renovations.
For Signing on the Dotted Line
5-7 p.m. daily
We’ve seen countless business transactions at Fleming’s over the years, including on a recent night, when some men shrugged off their suit jackets and got down to brass tacks over legal pads at the bar. It’s no wonder. The place feels like a clubby meeting room thanks to its warm wood accents, leather seating, back-lit bar and ultra-dim lighting. The cocktails and bar bites, which start at $6, are what you’d expect from this venerable chain. Start with the Bourbon Basil Smash, which is made with Maker’s Mark and has a sweet, herbal finish, or try one of the five excellent wines on offer. You can’t go wrong with the creamy homemade burrata, served with crispy prosciutto, tomatoes and crunchy garlic bread, or the juicy, meal-sized bacon cheeseburger ($9), which comes with a tangle of shoestring French fries.