How to Spend Your Summer in Southwest Florida

BY May 31, 2017

When the snowbirds are away, the locals will play. But play where, exactly? We year-rounders like to moan about the traffic, the parking, the nonstop galas in season—but when it’s all over, what do we do? Leave town. Take a vacation up North or overseas. Or, even worse, just sit in the AC all day.

Southwest Florida opens itself up over the summer. Yes, the heat is an issue. And so are the sudden showers. But don’t let those scare you away. We asked a few notable locals to share their secrets to a good time in the summer. So, come with us as we explore ways to make the most of your summertime on the Gulfshore.


Go island-hopping

The world comes here to vacation. When it goes back home, the year-rounders can take mini vacations themselves. Too often during season we get so stuck to our normal routes that we don’t veer too far off U.S. 41 or I-75. Yet just a weekend trip to a barrier island can remind us that we live in paradise.

Useppa Island is a mini getaway for many Southwest Floridians.

Christin Collins works 12-hour shifts some days during season as System Health and Wellness Strategic Business Partner for Lee Health, so summer is when her family can actually relax. Her favorite jaunt is to Useppa Island, a private island in Pine Island Sound accessible only by boat—and accessible only to members or their guests. There, it’s like a slice of Old Florida with a small-town feel to it. 

“Useppa Island is my absolute go-to. It’s my little piece of heaven. People travel to Useppa from all over, and here it is, right in our home. I’m so attracted to the water, so it’s the perfect place to be,” she says.

“My favorite part about summertime in Southwest Florida is that we locals are able to actually connect and get together,” she says, adding that she feels surrounded by like-minded people who are enjoying the local beauty instead of traveling elsewhere. “It’s a slow time in the charity (realm), so there’s a lot more downtime to go to an outdoor barbecue or a pool party.”

The Gasparilla Inn on Boca Grande features discounted room rates during the summer.

Meanwhile, J.P. Morgan wealth adviser Shanna Short and her new husband, Noel Davies, will be making the hour trip from Naples up to Boca Grande, where she’ll stay in one of the bungalows at the Gasparilla Inn. A two-bedroom villa in June, for example, runs for about $620 per night, about $200 less than in season. Just down the road is the inn’s private beach club, where they’ll grab a meal and then lay out overlooking the Gulf. Added bonus: The villas are dog-friendly, so Layla the pug will be making the trip, too. “There are so many great places nearby that it’s so much more economical to take a short road trip than to get on a plane,” she says.

Southwest Florida Community Foundation President and CEO Sarah Owen takes family day trips to Sanibel and Captiva islands. Traffic getting on and off the island is borderline unbearable in season, but once the crowds go, moving around the two-lane roads feels like a breeze. Owen and her family will head for YOLO Watersports, down the street from the popular beach pub The Mucky Duck. “My family tends to hit the water,” she says. “We take advantage of off-season rates on paddleboarding, kayaks and power boats and just explore.”  

Get moving

Part of the trick of surviving a Southwest Florida summer is getting a good breeze. Along the coast, sometimes the sea will take care of that for you. Other times, you have to do it yourself.

For Dan Costaregni of the Naples staple Pastrami Dan’s, the summer is about avoiding the heat. “The best thing in the summer is boating and the beaches—anything that will give you a nice breeze.”

Locals like Dan Costaregni will cruise the coast on relatively open waters during the summer.

He’ll zip around Naples on his motorcycle. On a nice day, he’ll take the family out on the Gulf. The chance to feel the sea air as he skims along the water is one of those experiences that make Southwest Florida great. “We also usually rent a boat from the Naples Bay Marina and head up to Keewaydin Island (which is accessible only by boat). On calm days, we take the Gulf side down.”

Eileen Connolly-Keesler, president and CEO of the Community Foundation of Collier County, says summer is the time of year when she and her husband, Pat, actually have time to get outdoors. “We go back to Wisconsin and people ask, ‘Why are you so pasty?’ Well, we are pale compared to the people who come down for a few months and bake in the sun. Summer is when we work on our tans!”

She’ll take walks on the beach, but a bike ride in their Pelican Bay neighborhood is ideal. The wide streets allow for plenty of space for both cars and cyclists. Nearby is Waterside Shops, which allows for a good rest stop for refreshment. Battling the heat is worth it sometimes, just to enjoy the ride sans the season traffic. “It feels safer,” she says. “When summer comes, we go out.”

“I love being here in summer,” she continues. “I don’t want to leave. Yes, it rains, but if you like hot weather, this is the place to be.”

Find the best beach spot

Live in Southwest Florida for a while and chances are you’ll start to neglect its main attractions—the beaches. In season, it’s almost not worth fighting the traffic and crowds. Summer clears the crowds, but for good reason. It’s not fun just to bake in the middle of the day. Melissa Cofta of Priority Marketing says timing is key. “I love that it’s lighter later. You can stay all day at the beach and not have to fight the crowds—and even see the sunset later on.”

The Heavenly Biscuit becomes less crowded in the off-season, much to the benefit of locals like Melissa Cofta.

For her, summer is a time to act like a tourist and head to Fort Myers Beach for a day. “I go to the beach just south of the Times Square area near DiamondHead Resort. There’s enough space where I can toss a Frisbee with my chocolate lab, Hershey. If you get there early enough for breakfast, I head to the Heavenly Biscuit for the fried chicken, egg and cheese. Usually, the waits are pretty long there during season.”

Off The Hook Comedy Club runs year-round, so owner Brien Spina sticks around for most of the summer, too. For his family, this is prime beach time. He’ll head to the Bonita Beach, where chances are you’ll be able to grab one of the free parking spots off Hickory Boulevard that can be hard to come by in season. “We just have a constant stream of guests who come down—family, friends from New York, New Jersey, Boston. That’s where we usually go with guests. I like it because it’s nice and quiet. A beautiful beach. It’s easy to get in and out of. We get out there and people tell me, ‘Yes, this is exactly what we came here for.’”

Grab a seat in your favorite restaurant

Sonya Sawyer will glance at her calendar during the summer and something will seem off. She doesn’t have anywhere to be. No galas, no fundraisers. The mother of two, CFO of Home-Tech and social maven actually has time to spare. “We get inundated. It’s great, but it does get to be a lot,” she says. “In the summer, we really just get to enjoy what everyone else enjoys during season.” That means dining out. She’ll be able to make it to happy hour at Angelina’s for half-off bottles of wine. At a favorite place like The Capital Grille, she’ll be able to get a reservation at a good time. And, she’ll get to check out new places like Ocean Prime on Fifth Avenue South. “We go to all the restaurants we couldn’t get into before,” she says.  

The Mad Hatter remains a favorite summer spot for Bob Cacioppo and his wife Carrie Lund Cacioppo.

It’s one thing to get into a restaurant. It’s another to actually get a seat. Barrett Farmer, director of the Naples Winter Wine Festival, targets good restaurants with prime outdoor seating during the summer. “We like to go sit at outdoor restaurants like Jane’s Café or Campiello. Jane’s is so sweet and quaint, we like to sit and enjoy the piece and quiet there. Anything outdoors really; the restaurants downtown have great patios to sit at. It’s so much easier to do things without all of the seasonal traffic and wait times.”

Now that the roads have cleared, Florida Rep founder Bob Cacioppo and his wife, Carrie Lund Cacioppo, recommend making the trip to a hidden gem: the Mad Hatter Restaurant on Blind Pass, which separates the two islands of Sanibel and Captiva. The white tablecloth dining room is “one of the finest dining experiences to be had in Southwest Florida and is situated for the perfect view of a sunset,” Bob says. (If you’re looking to make a weekend of it, they recommend Jensen’s Marina and Cottages—a throwback to when Southwest Florida was more rustic.)

Summer frees up time for chefs to get out and about, too. But, in the case of Naples restaurateur Vincenzo Betulia, he finds that he can never quite escape the kitchen. “I am always cooking, regardless where I go. I am too attracted to the kitchen to stay away. I just feel like it’s my duty to help out. I just can’t help myself. Last summer, at my cousin’s home, I got stuck cooking for 25 people in front of the grill. As everyone else was enjoying the water, cocktails, I was enjoying a glass of wine and the smell of the wood smoke. It’s what I love to do.”

Experience the natural world

Many locals use summer as a time to become one with nature—unlike season, where they become one with traffic.

We tend to forget as we get caught in traffic just how unique of an environment we live in. Just a few miles away from congestion is the peaceful tranquility of the Everglades.

Corkscrew Swamp Sanctuary Director Jason Lauritsen and his family use summer as an excuse to go explore nature a bit more. “One thing we love to do is go to Bunche Beach up by Sanibel and Wiggins Pass, especially on calm mornings, and look at the critters. Those are two great beaches that still have some pretty good natural habitat, like shore birds, hermit crabs and sea stars. … On really hot days when we want to be indoors, we usually go down to Rookery Bay and look at their museum and aquariums.”

In season, photographer Dennis Goodman spends a lot of time going to art shows to sell his work. Summer is prime to shoot. The month of June is always special for nature photographers—it’s when the rare ghost orchid starts to bloom. Goodman will head to Fakahatchee Strand to shoot it. Early summer is also when several species of birds start to nest. So, he’ll head to Marco Island to photograph royal terns or black skimmers and then to Estero Lagoon or Fort Myers Beach for shorebirds. “I can’t wait for summer,” he says. “It gets my creative juices flowing. It’s my best time to go out and create. When the rain starts, that’s when you get the clouds and all these great colors. It makes for great photography.”

Southwest Florida features some of the best fishing in the world in the summer.

One of the other main draws of Southwest Florida is fishing. Summer is when the tarpon start to jump. Auctioneer Scott Robertson, for example, escapes to cooler weather up North during off-season, but makes sure he returns to fish the water off Boca Grande for the silver king. Author Randy Wayne White, who used to be a fishing guide on Sanibel, stays in Southwest Florida in the summer as much as he can. He still lives on Sanibel and still fishes. “The fishing is great here. Tarpon, snook, bull shark—not sure if the bull shark will scare anyone off, though.” Another hobby he’s picked up recently: nature photography. “I love the afternoon showers. They sweep across and cool the day. I’ve taken to photographing the lightning. It’s fantastic.”

“I love summer in Florida,” he says, “because it’s a sultry, private time.”

True, and it’s not one to miss.

—Emily Rose contributed to this story.

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