Just over the iconic Ringling Bridge from downtown, the perfect day on these barrier islands would consist of a long brunch, shopping “The Circle” to your heart’s content, heading to Lido Beach to soak in the sun with a good book, then returning to St. Armands for dinner where the cuisine and people-watching are beyond compare.

When you look back on St. Armands’ history, you’ll wish you had a time machine and 13 dollars. That’s how much money its first homesteader, Charles A. St. Armand, spent for 131 acres in the 1880s to fish and grow vegetables. In the 1920s, Sarasota visionary, developer and circus magnate, John Ringling, purchased the island. He, alongside the Owen Burns Construction Company, laid out the plans for development. They envisioned a circle from which Lido Key, Bird Key and Longboat Key would radiate. Fast forward a century and their vision is reality as The Circle embodies Sarasota’s “it” factor while its surrounding neighborhoods embrace serenity.

Locals and out-of-towners can be found enjoying homemade fudge at Kilwins where it’s fun to wait in line, smell the aroma of sweetness, and watch as fudge is being cut and made. The Columbia Restaurant with its rich history and authentic Spanish roots is Sarasota’s oldest restaurant. The Crab and Fin is another favorite dining destination with its outdoor piano and delicious menu of seafood dishes. Or stop in at The Met, the perfect place to be pampered and shop ’til you drop with its combination day spa and fashion house.

Bird Key is a small island of 250 acres situated between downtown Sarasota and St. Armands. This residential neighborhood is home to newly built modern estates, Mediterranean-style residences, updated mid-century Florida ranch homes, and scenic canals that lead out to the Intracoastal Waterway and Sarasota Bay. The vibrant Bird Key Yacht Club and the Sarasota Yacht Club both celebrate community with boating, tennis and dining.

The island of Lido Key is home to beautiful white-sand beaches generally less crowded than the more well-known Siesta Beach. South Lido Key feels almost off the grid with a lush park, mangrove forests, and a quiet beach where four bodies of water converge. To the north, Lido Shores is a noteworthy neighborhood with some of the most luxurious and architecturally significant homes in Sarasota.

Heading north toward Longboat, if you blink you might miss the scenic peninsula of City Island. Introduced by a lone stoplight, the small sliver of land packs the best of the region’s science, dining, history and sports into 58 acres of pure cultural enjoyment. Many find their way here to discover the latest research of Mote Marine, grab a bite at New Pass Grill & Bait Shop and join the fleets of the Sarasota Sailing Squadron.

St. Armands, Bird and Lido keys offer a breezy blend of beaches, shopping and relaxed island living. Swim the warm waters, lay on the soft sand and walk along the beach, then stop for a quick cocktail or a delicious meal at one of the many restaurants that dot the area.