Sarasota has been dubbed the cultural coast because of its arts scene, but theaters aren’t the city’s only entertainment venues. Destination shopping is a pleasurable pursuit, and the region abounds with seductive retail diversions that are just as engaging as the best concerts, movies and plays.

Fabulous finds await in nooks and crannies along back streets and in sophisticated malls, quaint beach village shops and big-box discount stores. You’ll find the names you know, the brands you covet, and a whole lot of local-artisan-originality thrown in. Best of all, shopping comes with a special bonus here: the extraordinary service you’ll receive from our retailers, many of them big-city transplants who opened shop in Sarasota to live their dreams. Here’s our guide to making the most of your shopping experience.  

MAIN STREET, SARASOTA
It’s the quintessential Main Street U.S.A., smack in the middle of downtown Sarasota and retaining small-town charm yet valiantly stepping up to the consumer needs and wants in the 21st  century. Sarasota’s Main Street renaissance is better than most because its shops are set alongside (or beneath) luxurious new high-rise condos, built in anticipation of the mega-trend to retirement living in urban homes. The influx of sophisticated consumers is attracting high-end restaurants, galleries and stores, including a Yuppie food market (Whole Foods, off Main Street on Lemon Avenue) that’s become the go-to take-out place for busy young professionals.

Main Street has something for everyone, from snorkel gear to fine antiques, from fashion-forward boutiques to restaurants with European-style al fresco cafes. Some of the eateries are even open late at night if you want a stroll and a snack after a movie, the opera or theater.

PALM AVENUE & LOWER MAIN STREET
Every city has its own Palm Avenue, the stretch of shops that exudes luxury from its architecture and window displays to the quality of merchandise inside. In Sarasota, this district—located off U.S. 41 (also known as Tamiami Trail), just south and east of Main—is home to the finest art galleries, designer fashion emporiums and upscale jewelers and spas. When you’re ready to take a lunch or dinner break, choose a charming café or bistro; if you’re lucky, you’ll have great weather for people-watching as you dine outside. The parking situation, a bit discouraging during the condo construction boom, is easing up—but be prepared to walk a bit if you come during rush hour.

BURNS COURT & TOWLES COURT
Enough diversions can be found in Burns Court, a historic part of downtown Sarasota just off Pineapple Avenue, to keep you occupied for days. Burns Court is home to the region’s three-screen art-house cinema and a sophisticated mélange of restaurants, antiques shops and gift galleries. The funky secondhand shops are pure retail entertainment; the consignment shops are brimming with the discards of the rich and (locally) famous.

Nearby Towles Court, located off Morrill Street east of Osprey Avenue, is a genuine artists' colony that features live and work studio spaces for artists in a collection of restored 1920s cottages. If you’re here for the regularly scheduled Friday night art walk, you’ll meet and greet new talent in a lush tropical setting.

ROSEMARY DISTRICT
This up and coming part of town (along Central Avenue north of Fruitville Road) is reminiscent of warehouse districts across the country reborn as chic, avant-garde meccas for shopping and dining. Great stores for gifts, contemporary and modern home furnishings, and the latest beauty products are offset with a mix of restaurants that run the gamut from soul food to the newest trends in international cuisine. Don’t miss the region’s most intriguing architectural salvage shop and a tasting at a unique emporium of olive oils and imported treats.    

MIDTOWN PLAZA
Locals know this mall as the home of Michael’s On East, one of the region’s most acclaimed restaurants, with its full menu and prime steaks that are world-class. Just off U.S. 41, a bit south of downtown off Bahia Vista, this generic-looking shopping mall is patronized by locals for everything from café au lait to groceries. The mall houses a hair salon and the landmark Davidson Drugs, which stocks gift and souvenir items as well as a pharmacy and post office. A connoisseur’s selection of wines is available in an intriguing cellar that’s used for private parties and tastings.

SOUTHSIDE VILLAGE
You’ll want to peruse the entire length of this picturesque shopping and restaurant haven along Osprey Avenue a little south of downtown. Be sure to check out Morton's Market, a gourmet’s paradise filled with fine meats, fish, produce, a bakery and prepared foods. Many of the area’s other shops specialize in home décor and kitchen accessories; there’s a new lighting and furniture store featuring Danish design classics, as well as boutiques that offer imported art and gift items, including fine gold and diamond jewelry. Located in a residential part of town, the village is replete with service businesses that make life easier for those living and vacationing nearby. It’s also fun to tour the surrounding neighborhoods, which provide delightful examples of "old Sarasota" types of residential architecture.

WESTFIELD SOUTHGATE PLAZA
Located off U.S. 41 between Siesta Drive and Bee Ridge Road, this is the town’s most elegant mall, with shops both internationally recognized and locally acclaimed. It’s anchored by major department stores—Saks Fifth Avenue and Dillard’s—stocking several upscale brands you won’t find at branch stores in other nearby locations. The finest catalogue retailers have outposts here, and you’ll find beauty salons, a food court and casual restaurants set in an appealing environment with sun-lit dome ceilings. Check out the freestanding kiosks, with a range of unexpected treasures including bonsai plants and potted orchids. If the kids or husband are cramping your style, there are bright red "sports car" strollers for toddlers and relaxing massage chairs for the guys. No cinemas, but easy parking in a security-patrolled open-air mall lot.

SARASOTA PAVILION
Situated on U.S. 41, the main artery serving the Manatee-Sarasota-Venice communities, this open-air mall is off Stickney Road, the south bridge route to Siesta Key. The Pavilion is a great destination for bargain hunters, with its renowned fashion and home décor discounters and a plethora of nearby restaurants, including locally owned eateries and national chains serving breakfast, lunch and dinner. Most locals find the traffic patterns and parking areas at this mall awkwardly configured, and it's always crowded, so be careful parking and exiting.

WESTFIELD SARASOTA SQUARE
Walkers pound the pavement here when it’s too hot or rainy to exercise outside; grandparents bring the tots for lunch, ice cream and the soft-sculpture indoor playground. The major shopping destination on South Tamiami Trail (off Beneva Road), this is where teens congregate and families shop, catch the latest movies, and enjoy relaxed meals. Several new restaurants are available on site, or you can grab a quickie at the food court. The mall is fully enclosed, with easy parking in a massive lot. There’s a free-standing cinema, and a substantial renovation project is in the works throughout the mall. We’re already benefiting from improvements that outweigh any minimal construction inconvenience.

SIESTA KEY VILLAGE
This classic beach village, along Ocean Boulevard on Siesta Key, is just the right size, laid-back and brimming with stores that tempt even the most disciplined window shoppers to have a look inside. Tourists and residents head for Siesta Key Village before or after the beach; some come for lunch breaks, then head back to the shore for more sun and fun. Bring a swimsuit cover-up, flip flops and a credit card, and you’re good to go in any number of fine eateries, shops, bars and ice cream parlors. The mood is lively and casual in this strip of restaurants and boutiques: You’ll find hip beach attire and chic evening clothes, exquisite gold and silver jewelry, even souvenirs with artsy beach motifs. Most restaurants offer a choice of outdoor patio or air-conditioned inside dining, and some feature live entertainment after the sun goes down.

ST. ARMANDS CIRCLE
Historic St. Armands Key is a short ride over the Ringling Causeway from downtown Sarasota, but its ambiance is as sophisticated and chic as that of Newport or Rodeo Drive. The key once belonged to circus king John Ringling, who envisioned the barrier island as a summer White House retreat for President Warren Harding. But that never came to pass, and Ringling deeded the key to the City of Sarasota when he died in 1936. The presidential names of streets radiating off St. Armands Circle are a legacy of Ringling's grand scheme.

The Circle and side streets abound with restaurants and outdoor cafés featuring European, Caribbean and American cuisine, plus the best of Old Florida’s Cuban fare. Shopping here is as good as it gets, with art galleries, gift boutiques, upscale jewelry shops and clothing stores specializing in beach and tennis wear. St. Armands is both hip and family oriented: you can savor homemade ice cream and fudge or party into the night. Street parking is available if you’re patient; otherwise try one of the several public lots. If the shopping hasn’t worn you down, try the long, lovely stroll from the Circle to Lido Beach. 

VENICE ISLAND
A small-town atmosphere draws tourists year-round to the restaurants and shops along this wide shopping avenue that leads you right to the beach. The perfectly manicured retail district is adorned with trees, flowers and fanciful sculptures, making it difficult to decide whether you’ll spend the day browsing in town or walking along the shore. There’s a historic hotel, outdoor dining and lots of galleries and souvenir shops. Seasoned shoppers say that Venice, located in south Sarasota County and easily accessible from U.S. 41, has an Old Florida appeal that is irresistible. Venture off the main boulevard for some of the region’s most captivating teahouses, lunch spots, antiques and second-hand boutiques.

FISHERMAN'S VILLAGE AT PUNTA GORDA
A waterfront complex for shopping, dining, water sports and island tours, Fisherman’s Village offers exclusive boutiques, kitschy souvenir shops, food stands and elegant dining all under one roof. It is the spot to rent a fishing boat, jet skis or bicycles for leisurely tours of the picturesque community in nearby Charlotte County, a quick drive south from Sarasota via I-75. Choose from a half-dozen lovely restaurants arranged for maximum convenience and postcard eye appeal, or shop ’til you drop for artisan jewelry, rare shells, beach fashions, exquisite home decor or even snorkel gear.

UNIVERSITY CENTER
From designer shoes to gourmet gadgets, this open-air collection of shops and eateries (at I-75 and University Parkway, straddling the Manatee-Sarasota line) offers both impulse buying opportunities and focused shopping. Its convenient location near several new upscale communities and the interstate make it an increasingly popular shopping destination for local residents as well as tourists. You’ll find great buys on quality merchandise from clothing to fine china, wallpaper and furniture, but there are also deals on other items, from fur-lined jackets to discount sneakers. This mall brings local residents a much-needed fish restaurant, good Chinese take-out and several quality chain restaurants.

LAKEWOOD RANCH
While originally designed to serve the needs of this master-planned community, the shopping and restaurants here are attracting visitors across the region. From Town Center Market Square and the Lake Osprey Village retail center to the just-opened Main Street and soon-to-be-completed San Marco Plaza, the sprawling Lakewood Ranch, located off University Parkway in Manatee County, offers upscale choices with a hometown feel. Anchoring Main Street here are two Sarasota landmarks: Morton’s Gourmet Market and the Lakewood Ranch extension of downtown’s Burns Court Cinema. San Marco Plaza promises to be just as exciting, with architecture modeled after St. Mark’s Square in Venice, Italy. A mixture of upscale boutiques and restaurants, plus gift and specialty shops, makes this community a lifestyle trendsetter.

PRIME OUTLETS, ELLENTON
Regulars visit their favorite haunts often here, continually on the lookout for the hottest sales. But you’ll always save substantially at any of the dozens of outlet stores representing many of the world’s finest brands. The mall is arranged like a village, with covered walkways and lots of places to sit and rest while you plan your shopping strategy. If you truly intend to shop like the experts, plan to make Ellenton a day trip. Prime Outlets is north of Sarasota on I-75; its tile roofs and cheerful pink buildings are visible from the highway. Mediterranean courtyards, colorful mosaics and pretty fountains add to the allure. There's a spacious food court, offering international menus, and a mélange of stores for clothing, sporting goods, home furnishings, fine linens for bath and table, children's apparel, kitchen and electronic accessories, jewelry and cosmetics.