Explore Southwest Florida
Things to Do
in Southwest Florida
Three counties, endless experiences. Whether you are drawn to world-class beaches, cultural attractions, outdoor adventures, or simply the best places to watch a sunset, Sarasota, Manatee, and Charlotte Counties each offer something distinct. I have spent more than 30 years exploring this area. Here is where I send my own family and friends when they visit.
Updated Weekly
This week in Southwest Florida
October 15-18, 2026. Fall festivals, fine art shows, and seasonal markets are spread across all three counties this weekend. Here is where I would point you, county by county.
Sarasota County
Fall festivals in the Cultural Coast
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Sun Fiesta in Venice
Fri-Sun, Oct 16-18 in Centennial Park, downtown Venice. The city's signature fall festival with live music, arts and crafts, the Bed Race, and a Kid's Corner. Free admission.
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St. Armands Fall Festival of the Arts
Sat-Sun, Oct 17-18, 10 a.m.-5 p.m. around St. Armands Circle. Juried fine artists line the Circle's brick streets, right across the bridge from Siesta Key.
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Downtown Sarasota Craft Festival
Sat, Oct 17 at Five Points Park. The 30th annual downtown craft festival brings handmade goods and local vendors to the park.
Manatee County
BayFest and fall on the farm
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BayFest on Anna Maria Island
Sat, Oct 17, 10 a.m.-9 p.m. on Pine Avenue in Anna Maria. The island's 25th annual street festival with four live bands, a classic car show, food, and arts and crafts. Free admission.
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Hunsader Farms Pumpkin Festival
Sat-Sun, Oct 17-18, 9 a.m.-5 p.m. The corn maze, hayrides, pony rides, and live music continue this weekend in Bradenton.
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Dakin Dairy Farms Fall Harvest Festival
Sat-Sun, Oct 17-18, 10 a.m.-5 p.m. in Myakka City. A corn maze, hayrides, food trucks, and a kid zone on a working dairy farm.
Charlotte County
Fall festivals kick off in Charlotte
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Neighborhood Fall Festival at Laishley Park
Sat, Oct 17, noon-4 p.m. in Punta Gorda. A free family festival hosted by the Chamber of Commerce in the harborside park.
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Halloween Notte opening weekend
Fri-Sun, Oct 16-18 at the Charlotte County Fairgrounds. Haunted houses, carnival rides, a live show, and a pumpkin patch, gates at 6 p.m.
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Fall Home and Garden Show
Sat-Sun, Oct 17-18, 10 a.m.-4 p.m. at the Charlotte Harbor Event & Conference Center. Vendors, exhibits, and ideas for your next project.
Choose a County
Discover what each county offers
From the cultural energy of Sarasota to the laid-back charm of Charlotte County, each of these Gulf Coast counties has its own personality. Click through to explore the best beaches, dining, arts, and events in each one.
Florida's Cultural Coast
Sarasota County
From the world-famous white sands of Siesta Key to the galleries and theaters of downtown Sarasota, Sarasota County offers an unmatched blend of natural beauty and cultural richness. Explore the Ringling Museum, stroll through the Marie Selby Botanical Gardens, and discover charming coastal communities like Venice, Longboat Key, and Boca Grande.
Where Growth Meets Character
Manatee County
Manatee County stretches from the pristine beaches of Anna Maria Island through the historic riverfront of Bradenton to the master-planned communities of Lakewood Ranch. Known for its preserved natural areas, family-friendly atmosphere, and the vibrant Village of the Arts, this county offers something for every lifestyle.
Gulf Coast Exclusivity
Charlotte County
Charlotte County offers a quieter, more relaxed pace of life along the Gulf Coast, centered around the charming waterfront town of Punta Gorda and the growing communities of Port Charlotte and Englewood. Famous for its world-class fishing, stunning harbor sunsets, and the annual Florida International Air Show, it's a haven for boaters, nature lovers, and those seeking an authentic Florida lifestyle.
The Southwest Florida Lifestyle
More than just beaches
Year-Round Outdoor Living
With more than 250 sunny days a year, Southwest Florida is built for life outdoors. Kayak through mangrove tunnels, hike nature preserves, golf on championship courses, or simply spend the day on some of the most beautiful beaches in the country.
Arts & Culture Scene
Sarasota is known as Florida's Cultural Coast for good reason. World-class museums, live theater, symphony orchestras, film festivals, and art galleries punch well above what you would expect from a region this size. Culture is woven into daily life here.
Farm-Fresh Dining
The local food scene runs from waterfront seafood shacks to James Beard-recognized restaurants. Weekly farmers markets in every county bring fresh produce, artisan goods, and a genuine sense of community to downtown squares and waterfront parks.
Year-Round Festivals
From the Sarasota Film Festival and Venice Sharks Tooth Festival to the Florida International Air Show and Englewood Beach Waterfest, there is always something happening. Each season brings its own lineup of events worth planning around.
Family-Friendly Activities
Hands-on museums, nature centers, aquariums, trolley tours, and family-friendly festivals make the area easy to enjoy with children. Mote Marine Aquarium, the Bishop Museum, and Myakka River State Park are perennial favorites.
Boating & Water Sports
With Sarasota Bay, the Intracoastal Waterway, Charlotte Harbor, and the Gulf of Mexico, this is a paradise for boaters. Fishing charters, sunset cruises, paddleboarding, kayaking, and sailing are accessible from countless marinas and public launches.
Find Your Community
Exploring the area is the first step. Finding the right home is the next.
The best thing about living in Southwest Florida is that every county feels different. Whether you are drawn to Sarasota's cultural energy, Manatee's family-friendly communities, or Charlotte County's quiet waterfront lifestyle, there is a neighborhood that fits how you want to live. I know them all, and I can help you find yours.
Ready to make Southwest Florida your home?
I am Kim Donahue, your realtor with a heart to serve. I have spent more than 30 years helping people find their place in Sarasota, Manatee, and Charlotte Counties. Whether you are relocating, downsizing, or buying your first home in Florida, I would be honored to guide you.