There are so many reasons to travel, but good food is the core of all successful trips. Sarasota is home to hundreds of beloved restaurants serving local favorites, so don’t forget to pack plenty of pants with elastic waistbands.

Where to Stay

The Longboat Key Club is the best hotel for foodies. With five restaurants and lounges (only available to resort guests and club members), you could eat to your heart’s content without ever leaving the property. Plus, its proximity to downtown Sarasota and Anna Maria Island makes it a perfect launching pad from which to explore our rich culinary landscape.

Day One

Start your day in the Rosemary District in downtown Sarasota with a vanilla oat milk latte and vegan breakfast from Project that’s so good you won’t miss the meat or dairy. You could even grab a giant cookie for the road, although you may not need it as you snack through town. Afterward, take a quick walk down the block to Artisan Cheese Company, where you’ll find rare cheeses from around the world, as well as excellent house-made sourdough. Be sure to stay long enough to have a chat with owner Louise Converse, whom locals lovingly refer to as “Cheese Louise.”

If you’re in town on a weekend, schedule a Saturday trip to the downtown Sarasota Farmers Market, where you’ll find the most amazing Argentinian empanadas at the Empanada Girl tent. The caramelized onion and cheese-stuffed empanadas are worthy of praise.

Next, head to nearby Southside Village. There you’ll find Morton’s Gourmet Market, which is packed to the gills with fancy products. It’s a great place to stock up on snacks for the hotel room, whether you’re in the mood for charcuterie fixings, caviar or some of the best desserts in town. Afterward, walk down Hillview Street to Two Chefs on Hillview for even more grab-and-go options.

While you’re on your southbound journey, head to Siesta Key, where you can relax—and maybe take a food-induced nap—on its white sand beaches. If you stop by Daiquiri Deck on your way to the beach, grab a frozen daiquiri to enhance that nap in the sun. Once you’re feeling restored, visit the village one last time for a pistachio gelato from Made in Rome before catching a ride-share back into town.

You may be starting to fill up, but that’s no reason to skip dinner. Florence and the Spice Boys is a great spot for a light bite or a full meal inspired by the flavors of Israel and the Middle East. If you’re lucky, Florence herself might be there—her bright, bubbly energy fills the dining room.

Day Two

After a marathon first day of feasting, you may want to start day two at a more leisurely pace. Order room service at the hotel before taking a dip in the oceanfront pool. After all, it would be a shame to not take advantage of Longboat Key Club’s many amenities. You might even consider a paddleboard rental to build up your appetite for the day ahead.

For lunch, take a trip north to nearby Cortez, where you’ll find the perfect fish sandwich at Star Fish Co. Located right on Cortez’s fishing docks, it has the best location for one of Florida’s most famous lunches—just make sure to bring cash, since the restaurant doesn’t take cards. While you’re there, stroll the historic fishing village of Cortez, which is still home to many of Manatee County’s commercial fishermen.

Take the scenic route back to Sarasota by way of Longboat Key, where the Gulf of Mexico flanks the main road, making for a relaxing drive with stunning views. Follow Gulf of Mexico Drive onto St. Armands Circle, a food lover’s dream boasting more than 25 food-centric places to meet your needs. Crisp Waffle Company is a unique spot to people-watch while enjoying a Belgian waffle topped with tons of fresh berries and whipped cream. Or, if you’re in the mood for something savory, Crab & Fin has you covered with some of the best raw oysters in town. No matter where you stop, everyone back home will ask you if you visited “the Circle,” so spending a few hours there is a must.

After visiting St. Armands, head downtown to O’Leary’s in Bayfront Park, where the drinks are strong and the views of Sarasota Bay will put you at ease. The sandy shoreline is a great place for flip-flops, and in no time, you’ll be transported to the land of the late, great Jimmy Buffett’s song “Boat Drinks.”

When dinnertime rolls around, the options are nearly unlimited—but we recommend snagging a reservation at Indigenous in quaint Towles Court, where chef Steve Phelps serves sustainable seafood that’s as good for the soul as it is for the ocean. 

Insider Tip

Take it slow by sightseeing in each recommended neighborhood. Our town is filled with loads of interesting shops for when you simply can’t take another bite. And if you’re still curious about Sarasota’s many great restaurants, click here to learn more.