A wooden footbridge leading to the beach

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Classic St. Armands Circle

If you’ve spent any time on Longboat Key or in Sarasota proper, or done any amount of research on the area, you’ve heard of St. Armands. John Ringling’s fancy shopping circle is a bustling, beautiful promenade just steps from the beach, and its got a lot to offer the seasonal visitor, not to mention those who live here year round.

The circus magnate who bought the 132 acres that would ultimately be fashioned into The Circle was not the first to own them. That distinction belongs to a Frenchman named Charles St. Amand, who homesteaded on the barrier island in the late 19th century. When the land changed hands, St. Amand’s name was misspelled on the deed as “St. Armand,” a mistake that continues today. Ringling acquired the land in 1917 and started planning a high-end residential and shopping community to be shaped in a circle, just like a circus wagon wheel. Ringling Estates debuted in 1926 with much fanfare—including a parade—but the real estate crisis put an end to that. It wasn’t until the 1950s that things came alive again on St. Armand’s Key.

Today, it’s as much a park-like experience as a shopping and dining one. The Circle is a stunning showcase of Sarasota architecture, flora and fauna. It hosts art, craft, food and music festivals, as well as 30 pieces of Italian statuary, some from Ringling’s private collection. Over 130 shops and more than 20 eateries call The Circle home, so repeat visits are an absolute must. But there are some classic St. Armands institutions that really reflect the spirit and the history of this place.

The original Columbia Restaurant in Tampa might have been the first restaurant ever in Florida, but the one in St. Armands has its own unique flavor. Serving up all of the same beloved family dishes, this Spanish/Cuban spot is a date night waiting to happen. Sit on the breezy, Mediterranean-style patio and enjoy some sangria along with a bowl of the restaurant’s famous “1905” Salad. It’s hard to get more romantic than a night at Columbia, but Cafe L’Europe, established in 1973, manages it. This cozy, Old World-style restaurant has perfected classic European cooking and has the white tablecloths to enjoy eating it from. Head to long-standing Crab & Fin for local seafood and to Venezia, a relative newcomer to The Circle but making pies since 1966, for lunchtime pizza. While it’s not exactly on The Circle, no visit to the vicinity would be complete without lunch on the dock at Old Salty Dog on City Island.

The sheer number of retail spots here are a wonderful excuse to take your time meandering around The Circle, but a few are truly not to be missed. And some can’t  be overlooked anyway, like The Met Fashion House Day Spa & Salon, with its grand revival columns and elaborate staircase leading to a luxury clothing store. A second story boasts one of the best salons in the city. To look the part of a local, stop by Oh My Gauze! or Island Pursuit, both shops have that relaxed resort wear vibe down pat. For nighttime fashion, Foxy Lady has been dressing the area’s most fashion-forward women at this location since 1984; Armel Jewelers has been adorning them for 50 years.

One of the great pleasures of walking St. Armands is being enticed into one shop or another and finding some little treasure to take home. We love The Spice & Tea Exchange for this; it’s the perfect place to poke around in. One of the state’s premiere environmental photographers also calls The Circle home. Clyde Butcher St. Armands Gallery is chock full of the shutterbugs stunning work, which makes the perfect memento to take home. And if you’re planning on spending most of your time at the beach or pool—as well you should—head to Tervis. The tumbler-maker with the “Made For Life Guarantee” has been producing its cups from a factory just south of us since the 1960s.

Just a stone’s throw from St. Armands is Lido Key, the perfect place to stay for quick access to the The Circle and full of a variety of rental properties.