Think of Anna Maria Island as a seven-mile-long necklace with three cities shining like jewels: Bradenton Beach, Holmes Beach and Anna Maria. In each one, you time travel to the laid-back Florida of the 1970s. But along with mom-and-pop groceries, shell shops and modest beach motels, you’ll see gourmet restaurants, contemporary waterfront homes and intriguing boutiques and galleries. And surrounding it all, Sarasota Bay and the sparkling Gulf of Mexico.

Eat

The cutting-edge menu, from shrimp and grits to the beet-and-ginger-infused quinoa, at The Waterfront Restaurant, is fresh and locally sourced. Sit inside the charming cottage or outside to enjoy views of Tampa Bay and the Skyway Bridge. 111 S. Bay Blvd., Anna Maria, (941) 778-1515, thewaterfrontrestaurant.net

Blue Marlin Seafood makes its home in a 1920s cottage with nautical-style interiors on historic Bridge Street. The “Trap Yard” courtyard boasts a big covered deck and live music on weekends. 121 Bridge St., Bradenton Beach, (941) 896-9737, bluemarlinami.com

Zagat consistently rates Beach Bistro as one of America’s top restaurants. The wine selection is astonishing, the service stellar, and chef/proprietor Sean Murphy’s inventive mind is always cooking up something new. 6600 Gulf Drive, Holmes Beach, (941) 778-6444, beachbistro.com

You can wear your flip-flops while you enjoy peel-and-eat shrimp on The Sandbar’s Gulf-front deck. Inside is a tad more formal. The menu offers casual Florida fare with an emphasis on fresh seafood. Try the Tuscan-style mullet, stuffed with roasted garlic gremolata and topped with candied oranges. 100 Spring Ave., Anna Maria, (941) 778-0444, sandbar.groupersandwich.com

The restaurant on the Rod and Reel Pier is a seafood shack, improbably perched at the end of a long, rickety wooden pier. The fare is fish and burgers; the panoramic Tampa Bay vista—priceless. 875 N. Shore Drive, Anna Maria, (941) 778-1885, rodreelpier.com

Shop

At the Artists’ Guild of Anna Maria Island, you’ll find fine art by more than 50 regional artists. Many of the works depict island themes, so if you’d like to take home a piece of Anna Maria Island, stop here before you go. In addition, the guild hosts Holmes Beach Art District Art Walks every second Friday January-April. 5414 Marina Drive, Holmes Beach, (941) 778-6694, amiartistsguildgallery.com

The White Egret family of stores covers the island with a little bit of a whole lot of things: coastal furnishings, home decor, clothing and a wide selection of island-themed gifts. The Egret's Landing home furnishings and interior design, 5602 Marina Drive, Holmes Beach, (941) 778-2878; The White Egret home accents and gifts, 10006 Gulf Drive, Anna Maria, (941) 778-3782; and The Egret's Nest boutique, 10010 Gulf Drive, Anna Maria, (941) 778-8406, egretami.com 

At Back Alley Treasures & Bar, you’ll find custom-crafted jewelry, paintings and photographs by regional artists, women’s fashions and repurposed furniture. There’s a friendly little café, too, with pastries, coffees and craft beers. 121 Bridge St., Bradenton Beach, (224) 209-1480, backalleytreasures.com

Pink & Navy Boutique, with its island-style clothing for adults and kids, jewelry, accessories and gifts, is among the home-grown shops that line charming Pine Avenue. 216 Pine Ave., Anna Maria, pinkandnavyami.com 

Founded by the late former First Lady of Florida Rhea Chiles, The Studio at Gulf and Pine offers exhibits, art classes and lectures and also serves as a salon where artists and art aficionados interact. 10101 Gulf Drive, Anna Maria, (941) 778-1906, studioatgulfandpine.com

Do

Historic Bridge Street is a bustling, two-block enclave of souvenir cottages, galleries, boutiques, bars and restaurants. The Historic Bridge Street Pier juts 300 feet over Sarasota Bay. Bring your own fishing pole or grab a cold libation and fried clam strips at the Anna Maria Oyster Bar, right at the end of the pier. Gulf Drive North and Bridge Street, Bradenton Beach, visitbridgestreet.com

Just off the island, Cortez Village is a working fishing village replete with colorful Cracker cottages, timeworn boats, winding streets and dockside fish joints and markets. Start your visit at the Cortez Village Historical Society, then head to Star Fish Company & Restaurant for picture-postcard views and fresh Florida fixings. 12306 46th Ave. W., Cortez, starfishcompany.com

Charter a boat tour with Capt. Frank Jones on the M/V Minnow, which operates out of the Mainsail Marina on Holmes Beach. The boat accommodates 20, so bring your crew for dolphin watch and sunset tours or special adventures to Egmont Key. Or charter your own fantasy cruise. (941) 920-0092, mvminnow.com

Suncoast Fishing Charters offers inshore and nearshore fishing, night trips and sightseeing trips. You just might hook a 100-pound tarpon. (941) 356-4318, suncoastfishingcharters.com