Florida Keys and Miami Road Trip

Most of the time when I start dreaming of a new destination for the first time, I can point to several factors. Maybe it’s the setting of a book I’m reading. Maybe it’s getting a lot of press thanks to a news story. Maybe I have a blogger friend or two who visited recently and loved it.

In the case of the Florida Keys, one of my top dream destinations lately, I can point to one source. Bloodline.

My sister had been recommending the Netflix drama for quite a while, but it took me forever to sit down and actually watch it. Bloodline is about a prominent family in the Florida Keys: the parents (Sissy Spacek and Sam Shepard) own a luxury resort in the Keys; they’re pillars of the community. They have four children: a detective (Kyle Chandler), a lawyer (Linda Cardellini), a shipyard owner (Norbert Leo Butz), and a burnout who waltzes into and out of his family’s lives (the excellent Ben Mendelsohn, who won an Emmy for his role).

But behind this picture-perfect family are secrets, and crime, and murder. And the show raises questions about how far you’d go to protect your family.

(Just know one thing — Bloodline is a slow burn. I think it took me about four episodes to really get into it. I highly recommend you keep going even if you’re not sure how you feel about it — trust me, it’s worth it!)

What I love most about Bloodline was how it captures the Keys, and particularly paints a gritty image of the Keys — ratty local bars, grungy docks, and dirty trailer parks interspersed among the resorts.

I always had an image in my mind of the Keys being nothing but jaw-dropping beauty and luxury properties. This gritty portrayal was nothing like what I had imagined. And for that reason, I became obsessed with visiting this destination for myself.

I knew I had to visit the Florida Keys.

My friend Cailin and I decided to do a road trip through the Keys and Miami as an add-on to our trip to Universal Orlando. This jaunt would give us two nights in the mid-Keys, based in Islamorada, and two nights in Key West. (We were supported in part by Florida Keys Tourism; see the end of the post for details.)

Key West is like a completely different planet from the rest of the Keys — and for that reason will be covered in a different post. THIS post is about the Mid-Keys, stretching from Key Largo in the northeast to Big Pine Key in the southwest.

Here is the story of our trip to the Keys, told in a series of vignettes.

The New Hampshire of the South

As we drive into the Keys, I’m struck by the sensation that I’ve already been here — that this is a place I knew well.

It hits me when we drive into a sandy parking lot punctuated with palm trees. I’ve seen parking lots like those many times — only with pine trees. In New Hampshire.

Rural streets filled with discount souvenir shops, hawking cheap t-shirts and pool floats. Lots of prime waterfront space without any exceptional beaches of which to speak. Unpretentious restaurants where the dress code is nonexistent and hits from decades ago play loudly. Loud, warm locals that lean into your conversations and give no-nonsense answers.

Not to mention the sneaking suspicion that you would never want to get on the bad side of one of these locals.

This was what I grew up with during my summers camping in New Hampshire. Turn up the heat and humidity, add palm trees and mangroves, and the Florida Keys could be the same place.

Keys Drinking Culture

People in the Keys do seem to drink a lot. Locals do as well as visitors, a great number of them in their fifties and older. And this is a place where you can drink in abundance.

Cailin and I have driven all the way down from Orlando, a six-hour drive. It’s time to start our night at Ciao Hound, near Islamorada, a brand new Italian restaurant.

We start with prosciutto-wrapped shrimp and vegetables, then move on to heartier fare, a local beer, a sparkling water. It’s like heaven after a long day of driving. (Also, dogs have their own fancy dining area and menu here!)

Next we’re led back to the Tiki Bar behind the restaurant, torches flaming in welcome.

Cailin opts for their signature drink, a strawberry daiquiri and piña colada hybrid with a floater shot of rum on top. I’m driving that night, so I order a mojito and sip it slowly. Made with key lime-infused rum, I think that this is the best mojito I’ve ever tasted.

Didn’t you say the same thing about the mojitos at that salsa club in Cartagena, Kate?

I might have.

“Get off your phones!” the bartender yells at us. “You’re on vacation!”

Cailin and I stiffen. The reaction is to respond, “We’re working,” but that’s problematic. Sure, we don’t have to snap and Instagram and Facebook every moment of the trip, but we know our readers and our readers would love these pretty drinks. And most people would kill to do what we do for work, so to draw attention to what we do seems to be rude at best.

Where is the happy medium? Seven years into professional travel blogging, I haven’t found it yet.

We do at least put our phones away and walk over to the dance floor. A cover band is blasting “Beat It” while the intoxicated jump up and down, updating Michael Jackson’s iconic 80s dance moves with some modern twerking.

Cailin and I pose for snaps with a giant monster truck parked nearby and drive to our hotel.

Later on, we read about Snappers, a brunch spot in Key Largo with a make-your-own-Bloody-Mary bar. Might as well start the day right!

Reservations are necessary at this restaurant, I hear, and I make the requisite phone call, despite having developed a fear for calling strangers on the telephone in the age of texting.

Now — a brunch place with mandatory reservations sounds like it might be fancy or formal. Not whatsoever in the Keys. We dine outside underneath Samuel Adams-branded umbrellas, watching locals jet ski their way up and down the waterways.

The Bloody Mary bar is worth the hype. We’re each given a glass filled with vodka, ice, and a single shrimp, then are led to a table covered with bottles of juices, sauces, and accoutrements. Cailin is thrilled to discover that they have clamato juice and she can make a Caesar, Canada’s answer to the Bloody Mary. (Me: “So you’re saying there are clams in your tomato juice?”) I fill mine with pickles and peperoncinis and enough horseradish to clear my sinuses for the next month, then only drink a quarter of it because I’m still driving, after all.

The Keys has such a strong drinking culture, yet it’s a place where you can’t get by without a car. What did people do before Uber?!

Sunset Time

One night we head to Lorelei, a popular waterfront bar and restaurant in Islamorada. It’s a prime sunset spot, famous for its giant mermaid painted on the side of the road.

The drinks at Lorelei are terrific — Cailin and I both get key lime coladas. The food is meh. The key lime pie is an abomination. But that’s fine — the band consists of several men in their fifties playing covers of Green Day and Red Hot Chili Peppers songs.

People are dancing and partying until the band grinds to a halt and gives a speech talking about why we need to support our troops. (My non-American friends are always surprised to see this when they visit the States. It’s not common in other countries to talk this much about the military.) The band then transitions into a 3 Doors Down medley.

“3 Doors Down was one of few bands who actually played at the inauguration,” I tell Cailin.

Monroe County, home of the Keys, narrowly voted for Trump in the 2016 election.

We don’t talk about politics with any locals on this trip.

The sun goes down and everyone jumps up with their phone to photograph it.

“This is it. I love this,” says a white-haired man snapping shots with his Android, the brightness of the sun blowing out the rest of the sky.

“It’s great,” I agree.

“I know! I live here!” he exclaims, swaying in place to the band.

It’s something that I had missed for quite some time. American exuberance. Going up to strangers and starting a conversation for no reason at all. Less common in urban areas and the northeast but present throughout the nation, especially in this very American vacation destination.

It happens again on the trip. At a souvenir shop, I take of a picture of a bumper sticker reading SURRENDER THE BOOTY to text to my bud Jeremy, knowing he’ll love it. (Best left unexplained.)

A sixty-something woman sees me taking the photo and grabs my arm. “That’s my–” and she starts laughing so hard that she can’t get the words out. “That’s my — my — husband’s nickname!” She collapses in laughter; I tentatively join in before edging away.

How to Spend Your Days

Now, lest you think that the Keys are only for relaxing and doing little to nothing, you can fill your days with activities here, too.

Cailin and I start at the Florida Keys Brewing Company. It’s filled with all kinds of art, neon growlers and mermaid-tipped taps. The staff couldn’t be friendlier or more warm as they pour us a ring-shaped sampler.

The ingredients here come straight from the Keys — like Iguana Bait, a hibiscus-flavored beer. Go for the flight of 10 beers, featuring the best of what they have at the moment. I’m a big fan of the Coffee Stout and the Hurricane Hole Red.

The brewery is actually part of the Morada Way Arts District, a small collection of galleries and artists’ studios. Like most galleries I’ve seen in Florida, the landscape is the main subject. You won’t find gloomy art here.

For something quirky and different, Robbie’s Marina, just south of Islamorada, features tarpon feeding. you can buy a bucket of small fish and feed them to the huge, biting tarpons penned into the water.

It’s scary enough on its own. It becomes even more terrifying when the pelicans start chasing you, trying to snag the smelly fish for themselves.

Have I mentioned that my two biggest fears are fish and birds?

Despite that, it’s a lot of fun. Stay for lunch at the Hungry Tarpon.

For something more docile, visit the Turtle Hospital in Marathon and learn about the work that they do to save sick and injured turtles around the Keys and beyond.

Many of the turtles have “bubble butts” from damage that keep them floating on the surface. The hospital attaches weights to them to help them swim normally.

Panicking at the thought of being away from my gym for ten days, I look for Zumba classes and find one scheduled at the Cheeca Lodge, a gorgeous luxury property in Islamorada. As I drive onto the property, I grumble at being stuck behind a red SUV driven by a woman having a full-blown conversation with the security guard.

Eventually she leaves and I drive up.

“I’m just here for a Zumba class,” I tell the security guard.

“Oh, that’s your teacher!” she says, pointing to the SUV. I promptly drive after the vehicle to make sure I don’t get lost on the vast property.

Here’s something awkward: I’m literally the only person who showed up for class. That’s never happened before!

We do Zumba one on one, me dancing behind her in an upstairs ballroom. She’s got Pitbull on her playlist, which is my benchmark of a good class.

My teacher’s name is Denise. She’s from Germany. Like many people, she came to the Keys on vacation, considered spending longer, and when a job fell into her lap, it seemed like a sign.

I couldn’t imagine a place less like Germany. Perhaps that’s why she fell in love with it so much.

A Certain Kind of Girl

After several days in the Keys, Cailin poses a question: “There’s a certain kind of girl who lives here, don’t you think?”

“What do you mean?”

“They all have that look.”

Immediately, I know what she’s talking about.

The girls around our age work in the brewery and wait tables along the waterfront. They love to fish and go out on the water whenever they can. They’re open and friendly and loud, and they’re not afraid to call you on your bullshit.

These girls are deeply tan, what my family members would call “brown as a berry,” clad in denim shorts and worn tank tops with cheap sunglasses perched on their foreheads. Their hair is pulled back into sensible ponytails or worn down and wild, glinting in the sunlight in several different sun-bleached shades.

Could I live here? is a question that I always ask myself, everywhere I go. Could this be my life?

Living here would mean subverting the vast majority of my life. I could not be less like these girls. And not only  because my uniform is jeans, black tops, and tall black boots, which wouldn’t work for one minute in the Florida Keys.

These girls are interesting. Maybe it’s that they’re so different.

And then there’s the pie.

Key Lime Pie. World-famous, sweet and tart, made from the tiny limes that grow on these islands.

Every restaurant claims the best key lime pie of all. Most of them are lying. But taste is a subjective thing — you never know which one will appeal to you personally. The only thing to do is to taste them all!

If you’re in the mid-Keys, I recommend heading to Ma’s Fish Camp in Islamorada, the Blond Giraffe in Tavernier, or Mrs. Mac’s Kitchen in Key Largo. All of them serve excellent key lime pies.

Where We Stayed — Islander Resort Bayside

Islamorada was the perfect place to base in the Keys, and we stayed at a lovely little town home, the Islander Resort Bayside, for our two nights there.

I can’t tell you what we were more excited about — the fact that it was a two-bedroom apartment and we each got our own room, or that we had a washer and dryer! It was the halfway point of our trip and couldn’t have been better timed on either side!

I loved our little home. It was ideally located in central Islamorada, a short drive (or even a walk) from lots of attractions. There was a pool in the back overlooking the water.

It’s expensive to stay here, with nightly rates starting above $300. The Keys are incredibly expensive, though, and this is a standard price for a property of this quality. That said, you can save money by making use of the kitchen and cooking some of your meals.

The Takeaway

My time in the Keys feels like a dream. Not in a conventional sense when you can’t believe that you traveled somewhere so beautiful, but more like you just got back from a bizarre destination and you’re still trying to wrap your head around it.

Would I want to go back? Would I EVER. I feel like I barely scraped the surface of this destination. Plus, Bloodline has a third (and sadly final) season coming up. I’ll be Keys-crazy once again!

If you’re looking to plan a trip to Florida, I highly recommend the Keys. It’s a far cry from more conventional destinations like Orlando and Miami, and very different from beach destinations, but I think it’s the overall culture and feeling that makes it so interesting. I hope you agree.

Essential Info: While we based two nights in the mid-Keys and two nights in Key West, I recommend spending more time if you can, especially if you’re driving from far away. Budget at least three nights for Key West, possibly even more if you can afford it, and three nights would be great for Islamorada or elsewhere in the mid-Keys as well.

Feeding the tarpons at Robbie’s costs $1 per person and $3 per bucket of fish.

Tours of the Turtle Hospital in Marathon are $22 for adults and $11 for children.

The hourlong Zumba class I took takes place on Saturdays at 10:00 AM at Cheeca Lodge in Islamorada and costs $15. I recommend verifying before you arrive. You must call and book the day before.

The Keys, as you may have noticed, can be shockingly expensive, especially when it comes to accommodation. Rates at the Islander Resort Bayside start at $317. Find more hotels in Islamorada here.

If you’re a Bloodline fan, my friend Andy wrote a guide to the series’ season one filming locations.

Don’t visit the Keys without travel insurance — if you get injured on your trip, it could save your finances and your life. I use and recommend World Nomads.

Many thanks to Florida Keys Tourism and local partners for supporting our trip. We received several comps including accommodation at the Islander Resort Bayside, visits to the Florida Keys Brewing Company and Turtle Hospital, and meals at Ciao Hound and The Hungry Tarpon. Other expenses, including all other meals, activities, car rental and gas, were paid in full by me and Cailin. All opinions, as always, are my own.

Do the Florida Keys look like your kind of destination? Share away!

Click Here to find Keys and Miami Florida Rentals

Key West

Miami