May Wining And Dining Events In SWFL

Winter and Spring tourist season is behind us and there are new opportunities to discover or rediscover local restaurants and retailers. If you enjoy food and wine, this is where you'll find an ongoing list of May wining and dining events in SWFL.

Some establishments are still finalizing plans, so this is a work in progress. Check back periodically for updates. Finally, if you see something that sparks your interest RSVP as soon as possible. Most of these have limited seating and often sell out.

In the meantime, if you can't make any these events how about creating on one of your own. Here are five different wine and food pairings to inspire your personal May wining and dining events in SWFL. Gather your friends, try some new recipes and new wines to compliment them.

This rose is such a pretty shade of peach. It comes from Washington state and is made with juicy grenache grapes. Yet the wine is dry and a bit minerally. It has notes of cranberry, strawberry and citrus. I enjoyed it solo and with a caprese salad too. $20

This sauvignon blanc is from North Fork of Long Island. Pindar Vineyards is not as acidic or grassy and many sauv blancs. It is, however, tropical with notes of lemongrass. It goes down easy with salads and hanging out poolside. That's the way I tried it and recommend you try as well. $22.99

Yering Station was one of the first wineries established in Victoria, Austrailia in 1838. This is an aromatic and lively 100% pinot that has nice cherry notes. It's a lighter style, more fruity than earthy. The acidity makes it a great food wine. Make sure it has a slight chill to it.

Kaiken is from Argentina and Ultra is a dark, lush wine. It has dark fruit, herbs and spice that are beautifully integrated. I tried it with pork medallions and a dark berry gastrique. It would work with any grilled meats, think Memorial Day. The wine is a good value. $25

Casillero del Diablo has a partnership with the Mexican National Futbol Team and this limited-edition wine is part of the collaboration. This is a semi-sweet wine in a gorgeous bottle and makes for a great conversation piece. It was a big hit for some people at a pool party I recently attended. It's dark with vanilla and plums. If you like wine on the sweeter side, this is for you, with grilled and spicy meats, or maybe even dessert. $12.99

There are two Old Vines, one is a restaurant and wine bar in Mercato in North Naples. In addition, there is Old Vines Supper Club is on Davis Blvd near downtown. Make sure you arrive at the correct spot for these events. Reservations required. More info here   

This retailer is one of the premiere spots in Naples and Southwest Florida to learn about wine. They also have a restaurant on site to make dinners easy. The calendar will likely continue to book up. As of now, here is what to RSVP for in April. More info here.

Vichino's is in a small strip mall along U.S.41 in Bonita Springs, Bonita Commons. The coffee bar also has a nice selection of wine and calendar full of events. Some of those events involve wine and sunset wine cruises. More info here.

This North Fort Myers Farm is a gorgeous setting for a farm to table wine dinner. There are a few events to check out in May and not all are with wine. On May 21st there is a harvest dinner featuring tequila. More info here.

This beloved, chef owned Fort Myers restaurant has a series of summer wine dinners every year. The first one for 2025 features Long Shadows Winery in Washington on 5/7. More info here.

The Silver King restaurant inside of the Luminay Hotel in downtown Fort Myers is launching a new Wine Dinner Series this month. The theme is "A Night in France." Local, seasonal foods will be paired with a range of French wines. 6pm on 5/29. More info here.

This restaurant has a fully staffed, full-time wine tasting bar. You can stop by anytime, without a reservation to taste and learn about wine. They also have special events for even deeper dives. Cooper's Hawk has locations in both Naples and Fort Myers.

At the Naples location on 5/12 is Small Bites & Wine Flights: Junk Foodie. A food and wine pairing featuring your favorite junk foods.

Warren is a trendy restaurant near downtown Naples, known for its extensive whiskey and wine selections. While they do have wine events, in May it's the famous Pappy Van Winkle Whiskey. A selection of the highly sought after whiskies will be paired with food at this dinner on 5/8. More info here.