How to give a good tour of Sarasota
When you live in beautiful Sarasota, invariably you wind up giving a lot of tours to visiting friends or clients. I want to share with you the loop I do—starting from the north:
*I first point out the 1928 Ringling Museum at 41/University—and the fact there is no admission charge on Mondays for most of the complex.

*Turn right and head west to Bayshore to see some beautiful mansions, Jungle Gardens and take Indian Beach Road back to 41.
*Also along the North Trail, the Ringling College of Art and Design that began in 1931.
*Starting around 10th Street is The Bay, a public/private partnership on 52 acres. Within that is the 1969 Van Wezel.
*After that is the 1970 Hyatt that workers are knocking down this summer to make room for a smaller new hotel called Hyatt Centric Harborside. It will be part of a two-tower complex that will include 117 condos.
*I then point out the “new” 14-acre Quay—that used to be a popular one-building destination but is now a series of high-rise condos/apartments and five-star dining (Ocean Prime). Also within those 14 acres, the 1926 Belle Haven building that Sarasota Magazine described as “a flapper in an embroidered hat with a jade cigarette holder forced into a Zoom meeting.”
*Up next on the tour, I’ll mention the 2001Ritz-Carlton that now shares space with the Westin and The Vue, a hotel/condo combination that came along 15 years later.
*We’ll turn right onto the Ringling Causeway and head out toward St. Armands. On the way west, I’ll point out that beautiful Golden Gate Point used to be a road that led to the original bridge to Lido Key back in the 1920s. It was replaced by another lift-bridge in 1958, and then the current 65-foot-tall span in 2003.
*As we cross the bridge, I’ll point out the relatively new and improved Sarasota Yacht Club that had a huge makeover starting in 2008. After that is the tallest retirement home in the area–Plymouth Harbor, built in 1966.
*I’ll point out Bird Key and how Sarasota forefather and circus pioneer John Ringling had acquired a mansion for President Warren G. Harding to use as a winter White House but Harding died in office and Ringling’s sister lived in it instead. (St. Armands Circle was originally named “Harding Circle” and Ringling named the streets after Presidents.)
*We’ll go halfway around the circle, gesture toward Longboat Key (or even drive a third up the key until it starts to get repetitive), and go out to Lido Key Beach where my passengers are able to easily see the beach/gulf from the car on Ben Franklin Drive without leaving the car.

*Circling back around we’ll cross back over the Ringling Causeway where I’ll point out the beautiful skyline–which is even prettier at night.
*We’ll pull into the 1963 Marina Jack, drive a bit along the marina, point out pretty Bayfront Park. People love to see and often stop and pose with “Unconditional Surrender” also known as “the sailor and nurse statue.” The story about its original arrival of the 26-foot-tall statue in Sarasota in 2005–as well as the controversies and incidents around it–could take 15 minutes to explain.
*Back to the tour, heading south on 41 toward Selby Gardens where I’ll explain the new and controversial addition of a parking garage and restaurant that some neighbors protested. If time permits, we’ll turn right on Orange Avenue and head out to Siesta Key.
*We’ll drive through Siesta Village on the way in and point out the many casual shops and restaurants leading to the world-class beach. So as to not repeat my steps, we’ll loop back on Midnight Pass Road back to the north bridge.
*I’ll take Siesta Drive out to Tamiami Trail and turn left. Around then I’ll explain “Tamiami” is a contraction for Tampa and Miami. I’ll point out the beautiful old 1920s Sarasota High School building that is now an art museum. It’s described as a “Late Gothic Revival” building built in 1926. Classes moved to the newer high school building in 1996.
*As we head north on 41, we’ll take the fork toward 301 in order to point out Payne Park and the rare public tennis club that includes a dozen soft surface (Har-Tru) courts. Most public tennis courts are cement. It costs $10 to play but the club is closed on weekend afternoons.
*Turning left onto Main Street, I’ll mention that each block has such a distinct personality. The first section just had a big upgrade with an upscale apartment building that replaced an underperforming mall/office complex and reduced Hollywood 20 to just 11 theaters.
*The next block (Links) is on the brink of a big change. (Read: Lots of new condos.) I’ll also point out the former Herald-Tribune building that is visible evidence of the decline of newspapers.
*The next block of Main (Orange Avenue) includes lots of charming restaurants and an active nightlife that skewers younger in this section. The new Latin Quarter includes bands in the open front window that reminds me of the energy of the bars along Broadway in Nashville.
*Lemon and Main is the ‘epicenter’ of downtown, helped by the red-brick pedestrian mall the city installed 10 years ago. The 1913 Gator Club building used to be a grocery store, cigar shop, soda fountain and brothel. (If you stand on Lemon and look up at the building, you can see the individual bedroom windows upstairs.)

*As you approach “Five Points,” notice the flagpole and the short brick wall that includes a random sign that says, “Welcome buddies.” That is reference to a salutation painted on the street 110 years ago that welcomed home solders after World War I. Great trivia.
*The subsequent block is another mix of shops and restaurants, with a slightly sloped street and plenty of trees. It’s a lovely block.
*If time permits, I’ll turn right to show the Opera House, Selby Library, Florida Studio Theater and even the Rosemary District—or to the left to tour eclectic Burns Court.
I’m always proud to show off my adopted hometown. I fall in love with it all over again during each tour.
Feel free to print this tour and leave it in your car for your next tour. It’s only a matter of time.
Rayi Collins Photos
Ray Collins is an award-winning Realtor and former TV newscaster. He’s been published more than 200 times writing travel articles around the world. www.raycollinsmedia.com/articles