The Great Uber Escapade

Three women on a shopping-snacking-cocktailing spree try out Uber drivers to make their rounds from Fort Myers to Naples.

BY August 25, 2015


No denying it—there’s an abundance of things to do and places to go in Southwest Florida. But if you hate driving, like I do, then you’re out of luck.

Our little corner of paradise is spread out and not exactly famous for its public transportation, but we are infamous for our crowded roadways—especially during tourist season. I live happily on the shoreline of the Caloosahatchee River near downtown Fort Myers, and while I’d love to get out and explore more, I’m very fond of being alive and don’t relish the idea of risking my life just to experience Whole Foods in Naples. In fact, I absolutely refuse to drive on I-75. I don’t care how much faster it is than U.S. 41; being on that highway is like being on Mr. Toad’s Wild Ride at Disney World. When it comes to rides, I’m more of an It’s A Small World kind of girl. I like to take things slow and safe. Unfortunately, U.S. 41 is no pleasant kiddie ride either. It’s shocking to me that so many folks have apparently not gotten the memo about putting their cellphones down while operating a 4,000-pound hunk of metal filled with gasoline. Between the swerving, the tailgating and the rare use of turn signals—I give up.

Luckily, downtown Fort Myers has free trolley service. And I love it. It doesn’t go terribly far—only a block east of the Edison Ford Winter Estates, through the historic district and to the high-rise condos just up the river a bit. But, I take it everywhere—happy hour, the grocery, the theater, boutique shopping, and did I mention happy hour? Alas, my beloved trolley runs only November through May. In the summer, I’m left either to brave the road or put on some sneakers and hoof it. Obviously, it’s way too hot for that. My makeup would melt off after a block.

Because there’s nothing worse than being stuck inside all summer, I was thrilled to have recently discovered Uber, the ride-sharing service that’s operated via an app on smartphones. Actually, it seems I’m a little late to the game. When a friend mentioned she’d taken one home after a particularly festive girl’s night out and I asked her what an Uber was, she looked at me like I’d been living on a remote island without Internet for the past three years.

Uber is the brainchild of a group of young, tech-savvy entrepreneurs in California back in 2008. They were fed up with the shortage of available cabs in San Francisco. After lots of development, Uber went global in 2012, and the company is now worth more than
$40 billion (unregulated as it is, Uber is not popular with licensed taxi services around the world).

I can see why Uber is such a huge success. It’s a genius idea, and it’s super-easy. You simply download the free Uber app, enter your information, scan your credit card and you’re set. When you need a ride, the GPS in your phone locates you and shows you where nearby Uber drivers are. Tap “set pickup location” and the app lets you know when your driver will arrive (almost always within 10 minutes—unless you’re on a remote island or something) and shows you a photo of the driver and what kind of car he or she is driving. Most Uber drivers are in business as a second job to pick up a few extra bucks. And lest the idea of getting in a car with a stranger unnerves you, Uber drivers must be over 21, have a four-door car that’s newer than 2007 and pass a background check. I mean, we never seem to have qualms about hopping into a taxi cab with a driver who may or may not be a serial killer, so why not an Uber driver? Plus, Uber is less expensive than a taxi, and since the payment is handled through the app, no money is exchanged. Riders aren’t even supposed to tip.

It occurred to me that Uber could be the answer to my getting around Southwest Florida more often and venturing out of my downtown comfort zone. It wasn’t exactly the public transportation I’ve dreamed of, but since I’m fairly certain we’ll never have a subway system between Naples and Fort Myers, Uber could be the next best thing.


On a sunny saturday afternoon in June, I decided to put the idea to the test. I would “Uber it” from Fort Myers to Naples with stops for shopping, snacks and cocktails along the way.

But, I wasn’t going to do it alone. First of all, it’s no fun to have a girls’ day out alone. Plus, what about the aforementioned serial killers? I may talk a big game, but I’m not getting into a car with a stranger all by myself.

I recruited two fabulous girlfriends, Lynne and Valerie, who also love to shop, snack and cocktail. We met at a central location, the Green Market at Alliance for the Arts off McGregor. But just as I got ready to open the Uber app and get our first ride, Lynne asked, “Wait. What’s an Uber?”

“It’s a ride-sharing service,” I replied. “Someone’s going to show up here in a few minutes and drive us to Cru at the Bell Tower.”

“I thought you meant it was a cab,” she said, her eyes widening. “We’re just going to get in a car with a stranger?”

“Well, a cab driver is a stranger, too,” I countered.

“I’m not sitting in the front,” she stated.

Valerie, who recently toured Southeast Asia alone with only a backpack and is fearful of nothing, volunteered to sit up front.

Our first driver arrived in just 9 minutes. Fernando was young, well-dressed, clean-cut, extremely polite (he even got out of the car and opened our doors for us) and spoke very little English. Originally from Cuba, he drove an extremely clean Kia Forte. Valerie, who is trying to learn Spanish, practiced on him. After we arrived safely at Cru and ordered some delicious crab cakes and white wine, Lynne declared that she could easily get hooked on Uber. She was impressed that our 15-minute ride was only $9.92 and that when I tried to force a $5 tip on Fernando, he politely refused. But one of the cool features of the app is that you can rate your driver by giving them stars. We gave Fernando the full five-star treatment.

Next up, we decided a trip to Coconut Point Mall in Estero was on the agenda. Valerie wanted to go to the Apple store, and Lynne and I were up for another glass of wine and some fancy makeup at Sephora.


Our next driver, Harry, made us pine for Fernando. While the Uber app told us Harry was only 6 minutes away, it took him a good 15 minutes to arrive as we waited outside Cru in the sun. Ultimately, though, we couldn’t really blame him for getting lost in the Bell Tower parking lot—it’s a pretty big place. Harry, who was probably in his 60s, told us he was currently unemployed and had only been driving with Uber for a couple of weeks. He was a nice enough fellow, but his driving was a bit speedy for my liking. I saw Lynne checking the tightness of her safety belt, and Valerie, the one who fears nothing, texted me from the front seat: “He’s driving 70 mph in a 50 mph zone. Also, he’s only driving with one hand.”

That was all it took for me: “Ya know, Harry—we might not go all the way to Coconut Point—maybe we’ll stop somewhere else,” I said tentatively. But, looking at the stretch of 41 ahead of me, all I could see were car dealerships and convenience stores. Coconut Point was only 5 minutes away. “Never mind, Harry,” I said. “Just drive careful.”

When we arrived, as an experiment, I gave Harry the same $5 bill Fernando refused. Harry took it.

That ride rattled us, so we headed straight for the bar at Bice where we took advantage of the happy-hour vodka prices. It’s always nice to have a cocktail before shopping, but it certainly loosens the purse strings, as I spent plenty on fancy makeup at Sephora and sparkly accessories at Charming Charlie’s.


Next up it was Mercato in Naples with Justin in his Kia Optima. Justin showed up within 7 minutes, was in his 20s, strapping and very friendly. Not only that, we were his very first Uber passengers. Born and raised locally, Justin is an air-conditioning tech with a wife and baby—Uber-ing is a way to earn extra money to support his family—which is why I tipped him and why I was happy he accepted.

We had made it safe and sound to Collier County and as we sat down to dinner at The Pub Naples, we calculated our trip—to take three different Ubers to three locations from Fort Myers to Naples, it cost us just $47.67, plus $10 in tips. Obviously, that was more expensive than public transportation, but it was certainly less expensive than a cab (according to some fares we checked, a cab would have cost around $80, plus tip). Lynne and I agreed that despite the fact that none of our drivers attempted to murder us, it wasn’t something we’d likely do on our own. And, despite Harry’s racing, Valerie said she was OK with traveling by Uber alone.

We all agreed that Uber-ing across Southwest Florida was time-consuming, though. We had started out around 2 p.m. in Fort Myers and ended up in Naples at sunset. And while the shopping, snacks and cocktail stops were fun, we were Uber-ed out. Instead of forging ahead on another Uber adventure, I called my husband, who had been golfing in Naples, to retrieve us and take us back to Fort Myers. No app required, plus the ride was free, he was cute—and he drove with both hands.


Related Images: