Beginning at Clearwater Bay where Drew Street turns back toward the city center, Cleveland Street runs east to west, all the way to North Blecher Road. While a full 3.5 miles in length, the stretch that is most popular is the first half-mile, where landscaped sidewalks boast boutiques, bars and restaurants, and plenty of public art.
Capitol Theatre [405 Cleveland Street]
This vintage Art Deco theatre has had a long history as a vaudeville stage and movie house. Nowadays, you can catch big-name touring acts like Marshall Tucker Band and The Crash Test Dummies in an intimate setting of only 750 people. It’s the perfect stop for while shopping and eating up and down the street, just keep your eyes peeled for special events, like their after party and jam session following the Clearwater Jazz Holiday which often attracts the artists from the festival’s main stage.
GIOFFRÈ Boutique [8 South Fort Harrison Ave]
If you think the only place to find couture on the East Coast is in New York City, think again. This Milan-based fashion house also calls Clearwater home (the brand’s only US location). Located on the corner of Fort Harrison Avenue and Cleveland Street, the ready-to-wear clothes here are unlike anything else you will find in this shopping district, or anywhere else in Clearwater for that matter. The designs are chic and dark – think black crepe capes, leather high-waisted miniskirts, and floral velvet pantsuits. Just make sure to call ahead, this boutique is by appointment only.
Pour Yours Wine Bar [522 Cleveland Street]
This little wine bar is trying to make good wine accessible to everyone by turning the whole concept of a wine bar on its head. Rather than employing a team of servers who make you feel like you know nothing about wine, Pour Yours has chosen to opt for machines that allow guests to taste and discover wines on their own. Picture something like a row of soda dispensers, allowing guests to pick what wine they want and their preferred amount (either in one, three, or six-ounce pours).
La Fondita de Leo [528 Cleveland Street]
Chef Leo Caicedo has been perfecting Puerto Rican cuisine for the entirety of his 23-year career, so it’s no wonder that this trendy restaurant is considered some of the most authentic in the city. Their specialty is the mofongo, a dish made of mashed and fried green plantains that are stuffed with meat and sauces. Chef Caicedo serves them up four different ways – just like his grandmother taught him.
Tampa Bay Escape Room [625 Cleveland Street]
Race against the clock and solve puzzles to escape from one of this Escape Room’s three themed challenges. In either the Wizard’s Keep, Kidnapped, or Cabin in the Woods challenges, you get one hour to crack codes, solve riddles, and investigate everything to try to get out. Just remember, these rooms are designed to be beaten by anyone who walks in, so keep it simple and don’t overthink it.