Nightlife in Winter Garden

Coconuts Comedy Club, located in Jack’s Joint since 1998, has been luring in chuckle-seekers for more than two decades with a glittering stage filled with nationally touring comedians. To keep growling stomachs from heckling comedians out of frustration, visitors can mute tummy rumbles with a full menu bursting at the seams with saucy wings, 14-inch hand-tossed pizzas, and brawny steaks.

Veering away from the mainstream molds of personality-devoid coffee shacks, Tre Amici aims to establish itself as a local, independent hub for cappuccinos and creativity. Camp out on the squishy, orange sofas and admire local artwork while sipping on fair-trade and organic products. The full menu of hot and cold beverages includes the slushy latte frappamici with frozen espresso, milk, and a flavor shot ($4.75), chai latte ($4.20), and Italian soda ($3). Counter caffeine with a selection of good-for-you grub, such as Kashi oatmeal with either raisin spice and sliced apples, or brown maple and apple cinnamon ($2.95); organic low-fat yogurt parfaits layered with berries and maple-nut granola ($3.95); and hummus plates served with toasted pita ($5.75). Heartier fare includes crisp salads and gourmet sandwiches.

The Rack boasts impressive lunch, dinner, sushi, and cocktail menus at both the Hyde Park and Brandon eateries. House favorites include the Bomber ($12.95–$14.95), a specialty sushi roll of cooked and uncooked delights (snow crab, avocado, and asparagus topped with salmon, tuna, and eel sauce) served with tempura chips. Or blast through hunger with the Volcano roll’s cucumber, crab, cream cheese, avocado, eel sauce, and spicy mayo ($12.95–$13.95). Fusion appetizers, salads, sandwiches, single rolls, and chef special entrees round out The Rack's eclectic menus into a rolling billiard ball made of sticky rice.

Learn some new jokes to share with coworkers in the gladiator pit, laugh off a stressful week of gladiating, and don a neat blue poncho so that you can sit in the splash zone of some quick-witted stand-up pros. Coconuts books nationally touring comedians whom you've likely spotted standing in front of a faux-brick background on HBO and Showtime comedy specials, Comedy Central, sitcoms, movies, the Late Show with David Letterman, and the Tonight Show with Cormac McCarthy. Along with superstars, Coconuts also presents cut-ups on the precipice of superstardom, as well as local favorites with a preternatural understanding of the Floridian funny bone. Recent acts include Matt Sorrentino, Italian dolphin trainer Carmen Vallone, and viral videographer and NYC native Chris Jones. Check the schedule for more upcoming acts.

Wining and dining yourself is easy at Clearwater, whose eclectic menu will mollify even the grumpiest of your taste buds. Begin a romantic dinner for yourself and your cute hitchhiker with a starter of brandied shrimp ($9), hummus and grilled pita bread ($7), or a salsa trio with tortilla chips ($6). Ask your server to whip out the award-winning wine list and double-team your main course with a glass of Borsao ($7) and a chipotle chicken quesadilla ($9); a pairing of pizza margherita ($9) and Vicolo pinot grigio ($7); or, in celebration of the day you saw your first squid, a glass of Marcel Martin Tetê de Cuvée Brut Cremant ($10) and a specialty cinnamon-apple and brie quesadilla ($10). Stop in during the daily happy hour from 5 p.m. to 7 p.m. and say goodbye to the sad and perplexed hours with two-for-one house wine, or drop by on the second and fourth Friday of every month for a free wine tasting and live music.

As Tommy, one of Howl at the Moon’s piano players, explains on the club’s website, “Every night…we try and throw a party, regardless of whether it’s a Tuesday night or a Saturday night.” The bar’s trademark dueling pianos serve as the epicenter of these nightly celebrations; patrons submit their favorite songs on slips of paper for the pianists and backing musicians to recreate. If the website’s playlist is any indication, the bands can handle popular songs from all genres and eras, from Bon Jovi’s “Livin’ on a Prayer” to Kanye West’s “All of the Lights.” The performances are spirited: colorful lights splash upon a stage where servers, guests, and chairs that have somehow developed mobility all dance along to the music.

Fueling the celebration is the bar’s indulgent selection of drinks. Servers stand over patrons to plunge jello injectors into their mouths, and revelers grab colorful straws to help drain 86-ounce booze buckets filled with sangria or other fruity libations. Pomegranate liqueur and honey-infused whiskey sweeten specialty cocktails, and local beers add depth to coolers stocked with Stella Artois and Dos Equis.