A wooden footbridge leading to the beach

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Must Do: Downtown Sarasota

While there’s plenty to see and do along the coast, turn your attention to the city of Sarasota (it’s that gorgeous, glittering skyline that greets you upon your descent from the Ringling Bridge, FYI). Head for Downtown, where you’ll quickly discover some of the area’s best restaurants, shopping and cultural institutions. The Downtown vibe is friendly, relaxed and yet worldly at the same time–this is definitely the place to be if you love culture, nature and a really great cup of coffee.

The Downtown area is easy to get to. If you’re coming from the island, simply coast off the bridge and follow U.S. 41 as it wraps you around to Main Street. Or park at the Downtown Waterfront and grab a bite to eat at Marina Jack on the harbor before you cross the street to Main. The Waterfront boasts a beautiful park, amazing views and no-fuss food (with live music!) at O’Leary’s Tiki Bar & Grill, if you want something a little more casual than Marina Jack. Don’t know where to go first once you hit Downtown? Read on.

You Want To Shop

Luckily, there’s iRide, a free eco-friendly shuttle service that will take you anywhere Downtown–which means you can shop the whole day away and not worry too much about those bags. Glorious Bookstore1 is a fine place to start, seeing as it’s right there at the West end of Main Street. This shop is well-stocked with a range of selections and gifts, from local authors to New York Times Bestsellers.

Keep walking down Palm in either direction to get a taste of Gallery Row, as the locals call it. Several art galleries are nestled here, along with clothing boutiques and antique stores. For something a little different, head to Circus City Architectural Salvage and Sarasota Architectural Salvage, both on Central. Here you’ll find unusual home and garden items, all of them unique or vintage.

A clutch of boutiques await on Fruitville Road in an area called Historic Downtown Village (you can’t miss the candy-colored bungalows from the road). Elsewhere on Main Street, you’ll find shops selling everything from New Age items to rare books, along with quite a few clothing stores thrown in for good measure.

You Want An Amazing Dinner

You’re in luck. A great way to cap off your tour of Downtown’s Historic Burns Court is with dinner at Owen’s Fish Camp, a magical spot with a fun, down-home vibe. Try the fried green tomato salad and the oyster shooters. Another happening spot is Selva Grill, which serves up delectable Peruvian fare in a sultry atmosphere.

If you want a meal you’ll never forget, make a reservation at Indigenous, a modern American eatery run by a James Beard nominee from an old Florida-style home in Towles Court Art District. If you want music and food together, try local favorite Mattison’s City Grille or the always-hoppin’ Blue Rooster for some good old fashioned Southern comfort food.

You Want To Be Entertained

The Sarasota Opera House sits in Five Points Park, just across from the library. A typical season’s worth of shows includes concerts, opera recitals, youth opera performances, round tables, talks and more. One of the area’s most up-and-coming performance spaces is the West Coast Black Theatre Troupe, which offers a season of dynamic musicals, tributes and performances. Catch a movie at Burns Court Cinema, the film society’s hub, or at the East end of Main Street at Regal Hollywood Stadium 11.

You Want To People Watch While Eating Breakfast

Dining al fresco on Main Street is a popular pastime year-round, and several places cater to it. For a small bite and a leisurely coffee, stop in at Pastry Art to mingle with locals. Just around the corner is Boca Sarasota, which offers a sizable breakfast menu and a local-food focus. On Main Street, hit Made for award-winning brunch fare, or settle in at C’est La Vie, an authentic French cafe with all of the crepes you would hope for.

You could (and should) spend days exploring Downtown and its various neighborhoods, each of which offers a little something different in terms of local flavor. There’s always something new happening in Downtown Sarasota, so be sure to check the city’s event calendar before stepping out.