How to Give a Tour That’ll Make You Fall in Love with the City All Over Again
When you live in Sarasota, one thing is inevitable: sooner or later, you’re going to be hosting out-of-town guests. Whether they’re friends, family, or potential clients, they’ll all want the same thing—a grand tour of paradise. Luckily, you don’t need to stress. Here’s my tried-and-true Sarasota loop, a scenic, story-packed journey that blends history, glamour, and just the right amount of kitsch.
Start North: Culture, Mansions & Circus Legacy
Kick things off at the Ringling Museum, nestled at the intersection of 41 and University. Built in 1928, it’s not just opulent—it’s generous. Most of the complex is free on Mondays, so plan accordingly. From there, swing west to Bayshore Road where you’ll cruise past historic mansions, Jungle Gardens, and the charming Indian Beach Road.
Don’t miss Ringling College of Art and Design, founded in 1931—one of the engines behind Sarasota’s creative pulse.
Around 10th Street, you’ll hit The Bay, a gorgeous 52-acre waterfront park and public/private brainchild. Nestled within is the iconic 1969 Van Wezel Performing Arts Hall—a purple shell of a landmark with Frank Lloyd Wright DNA.
Glitz on the Gulf: Hotels, High-Rises & Quirky Throwbacks
Next up, you’ll pass the 1970 Hyatt, currently being torn down to make way for Hyatt Centric Harborside, part of a sleek two-tower complex.
From there, swing by the 14-acre Quay Sarasota. Once a one-stop shopping spot, it’s now a vertical neighborhood of luxury condos, Ocean Prime dining, and the preserved 1926 Belle Haven building—a flapper frozen in time, as Sarasota Magazine so poetically put it.
Continue to the 2001 Ritz-Carlton, and its neighboring pals: the Westin and The Vue, a 15-years-younger hotel-condo hybrid.
Over the Causeway: Islands, History & Presidential Dreams
Time to cross the Ringling Causeway—but not before pointing out Golden Gate Point, which once led to Sarasota’s original 1920s bridge to Lido Key.
As you ascend the bridge, look to the south and spot the revamped Sarasota Yacht Club (remodeled in 2008) and Plymouth Harbor, the tallest retirement home in town, standing proud since 1966.
Then there’s Bird Key, where John Ringling planned to house President Warren G. Harding—until fate had other plans. His sister ended up living there instead. The streets of St. Armands Circle, originally dubbed Harding Circle, are named after U.S. Presidents.
Loop halfway around St. Armands, gesture (or detour) toward Longboat Key, and continue to Lido Key Beach via Ben Franklin Drive. One of the few places where you can soak up a Gulf view without leaving the car.
Back to the Mainland: Skyline, Statues & Bayfront Drama
Heading back over the bridge, take in Sarasota’s skyline—especially enchanting at night.
Next stop: Marina Jack (1963), followed by a slow roll past Bayfront Park. Don’t miss the photo op with the towering “Unconditional Surrender” statue—also known as “the sailor and the nurse.” Its arrival in 2005 sparked more than a few local debates, and yes, there are stories.
Cruise south down 41 toward Selby Gardens, where a new parking garage and restaurant stirred up local controversy. If time allows, swing out to Siesta Key via Orange Avenue, breezing through Siesta Village before reaching that famed, powder-white beach. Loop back along Midnight Pass Road to avoid backtracking.
The Grand Finale: Main Street’s History, Hip Vibes & Hidden Gems
Take Siesta Drive back to Tamiami Trail (a mashup of “Tampa” and “Miami”) and point out the original 1926 Sarasota High School, now a stunning art museum in full Late Gothic Revival glory.
Turn north and take the fork to 301 to cruise by Payne Park and its rare Har-Tru clay tennis courts—$10 to play and worth every cent (as long as it’s not a weekend afternoon).
Make a left onto Main Street, where each block tells a different story:
- The first has a shiny new apartment complex and a downsized Hollywood 11 theater.
- The Links block is poised for condo-filled transformation.
- The Herald-Tribune building marks the slow fade of print journalism.
At Orange Avenue, the mood turns lively: think charming restaurants and a younger nightlife scene. The Latin Quarter even features open-window bands—bringing a Nashville Broadway vibe to the Gulf Coast.
Then comes Lemon and Main—Sarasota’s beating heart. The 1913 Gator Club, once a brothel (among other things), still stands tall. Look up and spot the second-story windows—each once its own… well, room for rent.
At Five Points, a brick wall reads “Welcome Buddies,” a nod to the hand-painted street greeting that welcomed WWI soldiers home over a century ago.
Wrap it all up with optional stops to see the Opera House, Selby Library, Florida Studio Theater, or swing left for a colorful spin through Burns Court.
Bonus Tip:
Print this out and stash it in your glove box.
You will need it sooner or later.
Because when you live in a city this stunning, the tours never stop—and neither does the love.
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Written by Ray Collins, award-winning Realtor, former TV newscaster, and globe-trotting travel writer with more than 200 published stories under his belt.
