5263 Ocean Blvd.; 941-346-1188; siestapi.com At the south end of Ocean Boulevard away from the more crowded sections of the village, 3.14 Pi Craft Beer & Spirits offers an impressive craft beer selection and cocktails to pair with some of the best comfort foods – including, yes, pizza pies, and baked chicken wings – on Siesta Key. Plus, there’s plenty of outdoor seating spilling out into the parking lot shared with sister restaurant Blasé Café. Beach Club 5151 Ocean Blvd.; 941-349-6311; beachclubsiestakey.com Established in 1947 and still one of the most popular bars in Sarasota County, Beach Club serves as a great spot to day drink, with select outdoor seats offering front-row views of the Village’s most bustling intersection. But it’s best known as a nightspot with DJs and other live music acts, a huge dance floor and various theme nights. Looking to meet a cast member from the MTV reality show “Siesta Key”? Here’s your best bet, along with Gilligan’s (keep reading.)