Best Summer Festivals in Southwest Florida

By: Susan Finch

Southwest Florida’s temperate weather beckons visitors and locals alike to get outdoors and experience everything the area has to offer. It also means festival season never ends where beachside music, fine dining, and plenty of art reigns. If you’re not sure where to start, here’s a round-up of some of the best festivals to explore in Southwest Florida.

A round-up of some of the best festivals to explore in Southwest Florida by Must Do Visitor Guides.

Friday Fest (Sarasota)

Van Wezel annual concert series features local Southwest Florida musicians with a line-up ranging from blues to rock and everything in between. The free outdoor summertime concerts in Sarasota typically run from 5 p.m. to 9 p.m. on the Bayside Lawn with plenty of food trucks and vendors to take in a sunset while enjoying live music.

SummerJazz on the Gulf (Naples)

Jazz lovers flock to The Naples Beach Hotel & Golf Club for SummerJazz on the Gulf that’s fun and family-friendly. Entertainers and musicians perform with a picture perfect view of the Gulf of Mexico as their backdrop while jazz fills the evening sky.

Rhythm on the River (Fort Myers)

Fort Myers is renown for its Edison & Ford Winter Estates with 20 acres of historical buildings, historic gardens, and the Edison Botanic Research Lab and the Edison Ford Museum. But during the Fort Myers presents Rhythm on the River, live music and dancing transform the Edison Coconut Grove. Dining, drinks, and plenty of music delights guests as the stars come out.

Shop, Dine, Rhythm & Wine (Periwinkle Place on Sanibel)

Shoppers have their own festival with live entertainment, dining, and wine at Shop, Dine, Rhythm & Wine at Periwinkle Place on Sanibel. Come hungry for refreshments from the local Blue Giraffe Restaurant and peruse shopping from jewelry to handmade soap.

Sunset Celebration at Time Square (Fort Myers Beach)

Southwest Florida needs its own sunset celebration to truly embrace its magic, and Fort Myers Beach delivers. Every Friday and Saturday from 6 to 10 p.m., guests gather to watch the sunset with live music. Performers play an eclectic mix of classic rock, reggae, rhythm and blues, and country.

Sarasota Powerboat Grand Prix Festival and Offshore Boat Races (Sarasota) 

The Grand Prix comes to Southwest Florida at the annual Sarasota Powerboat Grand Prix Festival with a week of family-friendly activities that get your adrenaline pumping. A downtown block party with photo opportunities with the team pilots kicks off a week of intense boat racing.

Naples Restaurant Week

A premier semi-annual event in Southwest Florida, Sizzle SWFL Restaurant Week, (formerly Naples Restaurant Week) spans over 14-days to celebrate fine dining at an affordable price. Their three-course menus start at $25 and offers guests the chance to try out gourmet dining across the area at local restaurants and hotels at a fraction of the price.

Savor Sarasota Restaurant Week

Sarasota celebrates their own restaurant week with Savor Sarasota with prix-fixe lunches and dinners at participating restaurants. Foodies enjoy tasting Peruvian to French and everything in between for a global culinary adventure.  

Evening on Fifth (Naples)

You don’t have to wait once a year to soak up some live music with fresh ocean air. Guests flood the streets on the second Thursday of every month for the Evening on Fifth in Naples. Restaurants and cafes open the doors to visitors looking to explore boutiques, shops, galleries, and dining options from 9th Street to 3rd Street.

There are more festivals and celebrations than you can possibly experience in Southwest Florida, which means it’s all the more reason to keep coming back!

Related Posts:

Written by: Susan Finch | Author Website

Susan Finch is a travel writer and content marketer for the tourism industry who spends her time obsessing over the latest travel trends, wrangling her small kids, and planning her family's next big adventure.

[gravityform id="2"]

Newsletter Sign-up