Quit monkeying around and try a Red Monkey in the Colony’s Monkey Room Bar with its walls of monkey murals. Made with orange rum, Amaretto Di Saronno and cranberry juice, it looks like a Cosmo, but is oh-so-much-more cosmopolitan. Why the monkey theme? The Colony’s founder, Murf Klauber, goes ape for the precious primates. Colony Beach and Tennis Resort, 1620 Gulf of Mexico Drive, Longboat Key. (941) 383-6464.
Consider the view through your martini glass: the Gulf, bay and Sarasota’s cityscape as seen eight stories up from Christopher’s on Lido. Inside your glass? Bar manager Sasha Odishelidze’s signature drink: an Emerald Rain martini, concocted with sour apple schnapps and premium vodka. Sip it while drinking in the view—and local artist Virginia Hoffman’s spectacular etched glass partition dividing the bar. Lido Beach Resort, 700 Ben Franklin Drive, Sarasota. (941) 388-5608.
Limit yourself to two Flirtinis at Michael’s Piano Bar—or your flirtatious tendencies just might go into overdrive. Served in cavernous 10-ounce martini glasses, this Sex and the City twist on the martini is made with strawberry Stoli, champagne, a pinch of Chambord, and pineapple juice. It’s the perfect accompaniment to pianist Joe Michael’s jazzy repertoire. 1212 S. East Ave., Sarasota. (941) 366-0007.
Rustic Grill’s bar manager Dawn Smithson enjoys introducing guests to the traditional Brazilian cocktail, the caipirinha. She prepares this tartly sweet and refreshing potion with golden Batuque rum distilled from sugarcane (also known as cachaça), fresh limes, sugar and ice. Sip a few and you’ll be daydreaming about taking a steamer to Ipanema. 1525 Fourth St. N., Sarasota. (941) 906-1111.
The original owner of Sarasota’s legendary Bahi Hut Lounge, Tom McClenithan, created his take on the Mai Tai in 1963, and Mai Tai devotees (people make pilgrimages to sample them) have loudly lauded it ever since. Tom’s son, Tim, now runs the Hut and won’t divulge the recipe except to say that he uses four kinds of liquors. It packs a potent punch, which is why they limit customers to two. 4675 N. Tamiami Trail, Sarasota. (941) 355-5141.
Selva Grill gets creative with its Peruvian-influenced Santa Maria, a mouth-watering mix of Stoli raspberry vodka, coconut rum, fresh mango puree and strawberries that’s so sweet and refreshing it seems to be impersonating dessert. Best sipped al fresco on Selva’s lively patio overlooking the bustle of Main Street. 1345 Main St., Sarasota. (941) 362-4427.
The Ca d’Zan Lounge at the Ritz-Carlton is celebrated for bartender Peter Whitely’s famous chocolate martini. Whitely doesn’t use just any old chocolate; his martinis employ luscious Godiva chocolate liqueur, to which he adds Stoli’s vanilla vodka and a splash of Bailey’s. If that weren’t dazzling enough, it’s served in a chilled glass with your initials carved in chocolate syrup. 1111 Ritz Carlton Drive, Sarasota. (941) 309-2000.
When it comes to vintage cocktails, nothing beats the Manhattan. First introduced around 1850, it became the epitome of urbane chic in the 1930s. This quintessentially adult drink is made with whiskey or bourbon, sweet vermouth and bitters, but Fred’s bar manager, Steve Olkowski, adds a dash of Dubonnet and dubs it the Midtown Manhattan. In a crowd of designer cocktails, this timeless classic stands out. 1917 S. Osprey Ave., Sarasota. (941) 364-5811.
Managing partner Aaron Redman got to concoct his own cocktail when he opened Roy’s Hawaiian Fusion in Sarasota. His Maui Mojito gives the traditional Cuban aperitif a Hawaiian twist by infusing a mix of Skye Vodka, Stoli Vanil, and Malibu rum in pineapples for a week. Add fresh mint and lime juice and you’ve got one big kahuna of a cocktail. Roy’s Hawaiian Fusion, 2001 Siesta Drive, Sarasota. (941) 952-0109.
If you can’t pass up cocktail hour without a dose of tequila, you’ll want to try Bonefish Grill’s Rita-Tini. This intoxicating fusion of martini and margarita is made with Margaritaville tequila, Grand Marnier and lime juice served in a martini glass. It may look like a martini, but the tequila within packs a wallop that will last way past the cocktail hour. 3971 S. Tamiami Trail, Sarasota. (941) 924-9090.
Our 10 Best lists are not ranked in order of numerical preference.