For more than a century, visitors have flocked to Sunken Gardens to gaze at exotic plants and pink flamingos. For decades, a vacation to Clearwater Beach hasn't been complete without a stop at Dairy Kurl, and the Gulfport Casino Ballroom has seen its fair share of dancing since opening its doors in 1934. For a tour of the area's classic attractions, don't miss these historic landmarks, old-school hangouts and slices of vintage Americana.
For more than a century, visitors have flocked to this sanctuary just outside downtown St. Pete. This 4-acre attraction features exotic plants, pink flamingos and more. City streets bustle just outside, but inside it's a tropical paradise. Don't forget to snap a pic of the iconic sign out front.
This mom-and-pop restaurant has been serving Coney Island-style hot dogs in downtown St. Pete since 1926. Sit on a stool at the old-school lunch counter and watch speedy short-order cooks prepare your burger, fries and milkshake.
This club has a revitalization story that makes local preservationists proud. Neglected for years, the world's oldest shuffleboard club was founded in 1924 and nurtured back to life a decade ago.
This Mediterranean revival-style building was built in 1924 and still maintains its Jazz Age grandeur with its arched ceiling and shimmering oak floors.
A beloved neighborhood dining spot since 1952, it was showcased on the Food Network's popular Diner, Drive-Ins and Dives. The vintage lunch counter and '50s-era soda fountain take visitors on a tasty trip back in time.
This family-owned restaurant keeps folks coming back for more because the food is great, the beer is cheap and the ambience is friendly.
Step back in timeat this 1950s landmark that's the last in a fast food chain that once dotted the southeast U.S. Regulars flock to theme nights showcasing vintage cars and motorcycles. Not a burger fan? Try Biff's onsite sister restaurant, Buffy's BBQ.
This is the oldest greyhound track in the country and it's still owned by the same family that opened it in 1925. Although the crowds are smaller these days, and the bar and gift shop are closed, the track endures as a reminder of days gone by (and the setting for several scenes in Oceans Eleven).
Located in Gulfport's artsy waterfront district, this art deco treasure has overlooked the shallow waters of Boca Ciega Bay since 1934. Enjoy dancing and entertainment all week long, but no gambling happens here.
The enormous sign has lit the Treasure Island skyline in vibrant neon since 1957. Though the amenities have been modernized, the hotel retains much of its mid-century appeal. Be sure to stop by the poolside tiki bar.
Generations of locals and Madeira Beach visitors know a trip to "Mad Beach" always ends with a scoop of ice cream from this mom-and-pop shop, which is easily spotted by its red-and-white peppermint striped awnings.
Those exploring St. Pete Beach have enjoyed the kitschy charm of this 18-hole mini golf course since the late 1960s. It's filled with madcap statues, making it completely photo-ready.
Folks who are extra hungry head to this family-friendly restaurant in Clearwater. An enduring local favorite since 1965, Angie's home-cooked grub and low prices keep customers coming back for more.
This sweet Clearwater landmark has been enticing folks on their way to and from Clearwater Beach for several decades. Nothing better than a delicious milkshake, malt or ice cream cone on a hot day.
Step back in time to another era at this Clearwater Beach motel that features a completely mid-century modern décor.
Formerly known as the Orange Crate Café, Old World meets new in this adorable cafe set inside a boxcar. Perfectly positioned next to the Pinellas Trail in downtown Dunedin, people watching goes hand-in-hand with a sipping fancy coffee and nibbling a healthy wrap or salad.
This quirky spot in Tarpon Springs is a slice of roadside America. Since 1968, the museum - using vintage dioramas - has educated visitors about the local Greek tradition of sponge diving.
