Incorporated in 1902, Sarasota has been home to many impressive residents, some of whom are household names wherever you live (like the late Paul Reubens, aka Pee-wee Herman). Decades after the city’s founding, in the 1940s, the Sarasota School of Architecture was established, creating Sarasota’s signature architectural look of sharp, clean lines and open-plan structures that invite the outdoors in.

Where to Stay

A Burns Square Historic Vacation Rental places you in the center of Sarasota’s historic Burns Court neighborhood. Constructed between 1924 and 1925 by the neighborhood’s namesake Owen Burns, this little pocket of downtown is teeming with architectural gems and walkable shopping. Nine rooms sleep between two and four guests, with plenty of amenities to take you out of your historical journey and back into the 21st century.

Day One

Summer Tap Juice Bar is just a hop and a skip down the street, and you can select from a variety of pressed tropical juices and gourmet toasts that are almost too pretty to eat. With starfruit juice in hand, you’ll be ready to face the day, which begins in Osprey, 10 miles south of downtown.

Selby Gardens’ Historic Spanish Point campus has been inhabited by humans since the year 300. Its earliest residents, the Manasota Culture, occupied the land for more than 500 years. Walk through the excavated shell midden tunnel, where you will see discarded bits of pottery, oyster shells and fish bones, all of which were used and consumed millennia ago.

Spanish Point’s history doesn’t stop with the Manasota Culture. Fast forward to 1867, when the homesteading Webb family settled the land—long after the last Manasotans migrated elsewhere—and opened a citrus packing and shipping company. After selling the property to Bertha Palmer, of the famous Palmer House in Chicago, the land became part of Palmer’s 90,000 acres of holdings in Sarasota, and the prize jewel where she built her winter home.

After meandering through Spanish Point’s many gardens and historical sites, continue south to Casey Key Fish House on Blackburn Point Road. Smoked fish dip has been a favorite among coastal Floridians for nearly as long as the state has been settled, and Casey Key Fish House serves a great version of it.

At the edge of the property lies the Blackburn Point Swing Bridge, which takes you to neighboring Casey Key. The bridge is listed on the National Register of Historic Places and is one of only a handful of swing bridges left in the state. Follow it to the barrier island and drive south to gawk at the many waterfront mansions.

At the south end of Casey Key, take a moment to park at Nokomis Beach and admire the mid-century pavilion designed by Jack West, an architect and member of the famed Sarasota School of Architecture. If time allows, dip your toes in the Gulf of Mexico and scoop up a handful of shells before continuing south to Venice Island, much of which was first constructed in the 1920s.

Once on the island, stroll the downtown area, with its many shops and restaurants. A scoop of ice cream is a necessity at Venice Avenue Creamery before you head back north for dinner at Owen’s Fish Camp, located a stone’s throw from your Burns Square bed.

Day Two

Today you’ll stick closer to town. Start the day with sun salutations at Shack Yoga + Fitness in the historic Rosemary District. Originally called Overtown, this neighborhood was the first Black community in Sarasota and has been home to many Black residents who were vital to the development of the city.

While there, walk to Sarasota by Segway, where you can hop on a tour of Sarasota’s most popular destinations, including Main Street, the Sarasota bayfront and the Ringling Bridge. Tours last for two hours and pack an informational punch—not to mention the fun of figuring out how to ride a Segway.

After the tour, you’ll cross the Ringling Bridge again to visit St. Armands Circle, which was built by another famous Sarasotan, John Ringling of the Ringling Bros. and Barnum & Bailey Circus. He built the bridge to Lido Key (home of St. Armands Circle) and was the first to drive across it in 1926. For lunch, visit Cafe L’Europe. The restaurant celebrated its 50th anniversary this year, making it a throwback stop for your historical tour. The French onion soup is the menu’s mainstay and is rich enough to fill you right up.

Take a short drive to neighboring Lido Shores, where you’ll find an architectural paradise of homes new and old. The neighborhood’s star Umbrella House was designed by Paul Rudolph and built in 1953. The home is open to the public a few times a year and is worth planning a trip around—but don’t stop there. The neighborhood boasts homes from many of Sarasota’s leading architects, past and present. Check out Architecture Sarasota, which is dedicated to preserving and celebrating Sarasota School homes, to learn even more.

At dinnertime, head down to Walt’s Fish Market for even more seafood (you’re in Florida, after all). Walt’s has been in the Wallin family since the 1950s and its menu details the family’s long Sarasota fishing history.

Insider Tip

To get the full effect of Sarasota’s past, you’ll spend plenty of time in the car, so download a podcast—Sarasota’s Compass Rose has one called “Navigating History”—or make a tropics-inspired playlist.