A visit to this Gulf-side city and its islands combines culture with beach time, making it hard to choose between viewing masterpieces at one of Florida’s most impressive art museums or frolicking barefoot on soft sandy shores, where drum circles and sand sculptures entertain beachgoers. So whether you turn urbanite one day and beach bum the next, you’ll find plenty of ways to make your stay in Sarasota stimulating, yet super laid-back.
1 Island Hop
Sarasota’s barrier islands are an adventure for sunseekers eager to explore by car and foot. Visit five Gulf islands, starting on Longboat and Lido keys, the farthest north islands. Then zigzag your way, traveling back and forth over bridges and causeways between island and mainland, to Siesta Key, Casey Key and Manasota Key.
2 Cruise the Sarasota Bay
Marina Jack in downtown Sarasota is the place to set sail into the Sarasota Bay. Take your pick from a dolphin-and-manatee watch cruise, a sightseeing cruise or a sunset cruise. You can even book a lunch or dinner cruise on the sleek two-story Marina Jack II.
3 Tour the Ringling
This elegant cultural complex is home to the Ringling Museum of Art, where everything from ancient antiquities to 20th-century paintings is displayed in jewel-tone-painted galleries. But there’s more. The Circus Museum, with its miniature model of an early 1900s circus city, is a history lesson on the Greatest Show on Earth. Cà d’Zan, John and Mable Ringling’s 1926 home, shows off Florida’s version of old-world architecture with its perfectly restored Venetian Gothic design. You’ll also want to meander through Mable’s rose garden; look for the Diana Princess of Wales rose.
4 Dine Downtown
Sarasota is notorious for its indie restaurants and downtown is a culinary hub where you can walk from one to another. So plan to enjoy at least one meal here, whether it be breakfast at The Savory Street International Café & Bakery (order the French Crater: scrambled eggs with ham, brie and bacon in a homemade bread bowl), lunch at Nancy’s Bar-B-Que (North Carolina-style pulled pork with slow-smoked baked beans) or dinner at Mozaic (Mediterranean-influenced dishes like duck leg confit couscous with poached pears and pheasant hazelnut sausage).
5 Shop and Stroll St. Armands Circle
Three blocks from the Lido Key beach, St. Armands Circle is the place to spend a Sunday afternoon. Walk the circle and its arteries; you’ll be tempted by fabulous signature prints at Lilly Pulitzer, classic nautical sportswear at Island Pursuit and cutting-edge designs at Foxy Lady. Art lovers with a penchant for marine life art stop at the Wyland Galleries. When you’re legs can’t take another step, grab a sidewalk table at Café L’Europe, order a glass of chilled white wine and people watch.
6 Tour Exotic Gardens
The highlight at the Marie Selby Botanical Gardens is the Tropical Conservatory. Among the epiphytes you’ll see in this warm and humid greenhouse are species you won’t find at your local Home Depot’s garden shop. Think rare orchids and bromeliads nestled into the greenest foliage that makes you feel like you’re in a rainforest.
7 Catch a Show
Fondly called the “Purple People Seater” by locals, the Van Wezel Performing Arts Hall, painted a vibrant shade of purple, sits on the edge of Sarasota Bay. In a town where life revolves around the cultural scene, this Sarasota theater delivers stellar lineups season after season. Not only Broadway musicals and the Sarasota Ballet, but pop concerts and performances by comedians the likes of Joan Rivers and Bill Cosby draw both residents and visitors.
8 Bicycle Siesta Key
Siesta Key Bike & Kayak rents beach and road bikes near the intersection of Midnight Pass Road and Stickney Point Road, the crossover to Siesta Key. From here pedal south under the shade of wide-spread banyan trees and peek into the backyards of beachfront Mediterranean-style homes and cozy bungalows. Bicycle north of Stickney Point Road and you’ll reach Siesta Key Village, where you can poke into shops or cool down with a cone of Key lime ice cream at Big Olaf Creamery, an ice cream shop run by the Amish.
9 Beat the Drum
You haven’t really been to the beaches of Sarasota until you’ve participated in a sunset drum circle. Men of all ages assemble with their bongos and tom-tom drums, beating out a boom-boom rhythm as hundreds form a circle and dance on the sand to celebrate the Gulf’s glorious sunset. The unpredictable, informal drum circle is usually held on Casey Key’s Nokomis Beach on Wednesday and Saturday.
10 Loll on the Sand
Everyone needs a beach day and Siesta Key is the most sought-out stretch for its powder fine sand and dramatic crescent shape. Bring a chair and spend the day. Stroll the shore and you’re sure to find some impressive sand sculptures by resident “artists,” who are regulars on Siesta Key’s beach.