NOW - SEPTEMBER 4

The Generous Pour Wine Event at The Capital Grille

Choose from a hand-selected collection of wines to craft your own personalized wine dinner at the eighth annual Generous Pour event. The wines are all specially selected by The Capital Grille’s own Master Sommelier George Miliotes, who is one of only 215 Master Sommeliers in the world. 180 University Town Center Drive. Tickets are $28 per person with dinner.

NOW - SEPTEMBER 21

Innovative Dining Cooking Classes

Explore the unique culture and cuisine of Southeast Asia, the Mediterranean, South America and many more regions during Innovative Dining’s summer cooking classes. Each class focuses on learning and experiencing the culinary delicacies of a specific region, and includes an open beer and wine bar. There's one today focusing on Southeast Asia; buy tickets here.  $95; 8130 Lakewood Main Street.

AUGUST 13

4th Annual Cupcake-Eating Contest at Heavenly Cupcakes

If you think you and your sweet tooth can handle it, sign yourself up for the fourth annual Cupcake Eating Contest at Heavenly Cupcakes. All participants will receive a jumbo cupcake (choose from four flavors) and a free Tervis Tumbler, but those who finish the massive cupcake will win a free shirt and, of course, bragging rights. 6538 Gateway Avenue. Tickets are $40. Buy tickets here.

AUGUST 14

J.R.’s Old Packinghouse Café Fundraising Concert

Wrap up your summer with a music festival fundraiser for J.R.’s Old Packinghouse Café, a local favorite that has been closed since June due to damage from a fire. Come support this iconic restaurant and enjoy live music, a full buffet courtesy of chef J.R. Garraus, silent auctions and raffles all day long. 7289 Palmer Road. Admission is $10, buffet is $10.

AUGUST 18

Salute to Summer Wine-Pairing Dinner at Mattison’s Forty One

Indulge in a five course wine-pairing dinner, all personally crafted by Chef Paul Mattison. From local farm foods to fresh Florida seafood, the food and wine pairings offer a perfect way to say farewell to summer. 7275 South Tamiami Trail. Tickets are $85 plus tax and gratuity. Buy tickets here. 

AUGUST 20

Sarasota Beer Fest

Head over to the Robarts Sport Arena for a day filled with unlimited specialty beer and food samples from some of Sarasota’s local eateries. The event will feature live music and a photo booth, and all proceeds will benefit those who have served in the military and their families. 3000 Ringling Boulevard. Tickets are $30. Buy tickets here.