A guide to seeing the most of Florida by car.

Do you remember February?

It was actually this year, but in 2020 that may as well be a lifetime ago. I was still going to trivia night! I was still going to yoga classes! I still had a job!

Italy was still a week from shutting down, and we still felt arrogantly untouchable by news out of China, so my friend Susan and I flew to Florida for this thing most of us used to do sometimes, called a vacation.

I cannot conjure that mental state anymore, but I have photo evidence that it’s true, we did go. And we did one of my favorite kinds of vacations, a road trip! We started in Miami, then drove down to Key West, then through the Everglades and up to Tampa.

If that was my last trip for this year or even next, it was a pretty epic one. On the one hand, I marvel that we were so oblivious of what was to come. On the other hand, I envy myself that obliviousness. Looking at these photos hurts a little bit, because it was honestly the last time I felt totally relaxed.

I wonder if anyone really wants to read about the before times right now (especially right now, as so many are trying to protest police brutality and advocate for their rights amidst the pandemic), but I think people need to know about Florida. I didn’t really know about Florida! I just thought there was Disney World and Waffle House, but not much else to recommend the state, and I was wrong. Florida really surprised me! Best of all, I think Florida is a state made for road trips.

In Florida, we found mermaids! And watermelon sushi, crystal blue water, white sand beaches, and key lime pie. So! Much! Key! Lime! Pie!

I have to believe that all of these wonderful things will be there in the after times as well and I have a hunch that in the near or distant future we will all be in search of a little joy. So when it’s time for your road trip in Florida, I insist you know going in how awesome it’s going to be.

Miami & Miami Beach

Oh, Miami, what can I say?

Before this trip I had only ever had a layover in Miami, and it wasn’t really at the top of my travel wish list. Of course, I love The Golden Girls and Jane the Virgin, and Blanche, Rose, Dorothy and Jane all seemed to love Miami (well, Blanche mostly seemed to love the men in Miami). But the only other thing I really knew about it was that it’s a favored city for celebrities, and anytime I knew anyone who went there, they’d rave about the clubs and the nightlife, and clubs and nightlife aren’t my preferred vacation mode.

But guess what? Everybody is right about Miami! It’s the best.

We joked we were doing the Golden Girls version, with cheesecake and an early bedtime, but right on day one that plan died in the face of stone crab, vegan sushi and good cocktails. Our first evening was rainy and windy, but even so, Miami Beach was pulsing with music and crowds, and just a walk down the street was enough to feel the energy. Red eye exhaustion has no chance against all that.

For our only full day in Miami, we made the absolute most of it! We walked along the beach until the humidity got to us, then headed across the water to Miami proper, to kick off what turned out to be a mini cubano and mojito crawl in Little Havana, then over to Wynwood to see the walls and murals. If you like street art, I highly recommend!

At that point, we were completely stuffed with cubanos, ice cream, pastries, and even a mini key lime pie, so we thought we’d walk back to downtown for our planned ceviche dinner. Susan and I are seasoned pedestrians, but between the heat and humidity and the miles we had already walked, even our feet gave out, just in time to discover that Miami’s downtown area has a FREE public transit system!! WHAT. I think San Francisco should get one of those. Miami doesn’t even have hills!

The next day, we had to head out early for the drive down to the Keys, but we made time to drive up near the Fontainebleau and the boardwalk up there, where I got my only decent shots of the beach in Miami, then on our way south we stopped for arepas, which were delicious, huge and filling, perfect sustenance for the drive South.

We never did get any cheesecake, but we saw just enough of Miami for me to be sure I want to go back.

Top Miami Eats & Drinks:

Joe’s Stone Crab I arrived first in Miami, and I had a very grumpy afternoon alone in Miami Beach. All I wanted after my red eye was a long walk to stretch my legs, but it was pouring rain. So I decided to treat myself to an early dinner while I waited for Susan to arrive, and I headed here, where I figured some fresh seafood and a slice of key lime pie would cheer me up. I suspect I may have been their first solo diner ever, but it was fantastic! The crab is sweet and tasty (and already shelled!) and the pie was excellent ( if you want to keep track this was key lime pie #1).

If you go, try to go early! They open at 5 pm for dinner, I got there at 5:08 and got seated at 5:45. There is a massive bar you can wait at, so you can have a drink (or 2), but they don’t serve the full menu in the bar, so be prepared to wait.

Planta Once Susan arrived, she was hungry, and I was like, “I could eat,” but since this was my second dinner of the night I suggested this vegan place I had heard of, as it might be a bit lighter for me. I’m so glad I was selfish, because this was hands down one of the best meals of the whole trip, if not the best. This place serves vegan versions of almost every type of cuisine. We had watermelon sushi, queso dip, truffle steamed dumplings, and a coconut ceviche that was so good that Susan, a bit of a ceviche connoisseur, proclaimed it one of the best ceviche’s she’d ever had. As someone who can’t usually get past the rawness of raw fish in sushi and ceviche dishes, I was in heaven.

Azucar Ice Cream Company I think I first heard of this little ice cream shop while watching the Cooking Channel, and luckily I remembered it, because their abuela maria flavor, with a guava ripple and Maria cookies throughout, is one of the best cones I’ve had in a while. The ice cream wasn’t overly sweet, so it felt actually refreshing as I stood in 90 degree heat, eating it as fast as humanly possible in a battle with the elements.

Old’s Havana Our first stop for cubano sandwiches and mojitos was actually Versailles. I was pretty underwhelmed there to be honest, and when I had the first bite of my sandwich here, I knew instantly that what I had eaten earlier was not actually what a cubano is supposed to be. This cubano, however, was it! I’ll tell you a secret, actually serving it hot is key! My first sandwich was barely heated through, as if they had only given it a cursory press. This one was almost molten when it came out, with crisp bread and cheese pulls for miles.

Zak the Baker I had read about this bakery on many “top” food lists for Miami, and since it was in Wynwood, we decided to stop here on our way to see the Wynwood Walls. I ordered one of everything that caught my eye, so of course it was too much. But I snacked on the goods for a few days while we were in the Keys (probably too long honestly given the humidity). My favorite was the guava and cheese pastelito, a Miami staple I did not try enough of.

Pink Pie During our Wynwood wanderings we found this cute little pie and matcha cafe. When I say little pie I mean tiny pie. We tried the key lime of course, and it was maybe 2 or 3 bites and small enough to fit in the palm of my hand, perfect for snacking (key lime pie #2).

Doggi’s Arepa Bar One thing I learned from Jane Villanueva (other than to double check with your doctor that she’s not artificially inseminating you) is to not go to Miami and skip the arepas. The arepas here were excellent. I never knew that chicken salad and shredded beef went together but they do, and I learned that here.

Where to Stay in Miami:

There’s Miami, and there’s Miami Beach, and choosing where to stay should depend on your plans and your tolerance for loud music. We knew we’d only be in Miami for two nights, with only one full day, so we decided to go for the full experience of Miami Beach and stay there. You’ll need your earplugs, and the row of art deco buildings housing boutique hotels and thumping clubs are definitely a scene, but it’s a fun scene even if you don’t plan to partake in the nightlife. I’d recommend it for first-timers to really soak up some of the atmosphere.

Day Trips from Miami: Biscayne Bay National Park, Everglades National Park, & Homestead

You might not know it, because it can feel worlds away, but Miami is super close to a lot of other Florida destinations, easily accessible in one day by car. So whether you want to do a day trip or are deciding where to go after Miami, be sure to check out these places!

Biscayne Bay

Our visit to Biscayne Bay wasn’t more than a glorified pit stop, but we stopped there so we could complete the National Parks trifecta of Biscayne Bay, Everglades, and Dry Tortugas. Check!

There isn’t much to do at the park if you don’t plan to go boating or kayaking or fishing, but the vistas are stunningly scenic, and the park ranger gave us some intel on her favorite, lesser-known, secluded beach in the Keys. The beach turned out to be neither secluded nor lesser known, but I’ll give her points for friendliness!

Everglades National Park

The Everglades, despite only covering half of its original land area, still feels massive when you are driving through it, and it would probably take days to visit all the various sites it has to offer. But if you are in the Miami area, the eastern edge is very accessible, and is home to some gentle walking trails, complete with gator sitings aplenty (because we all know that’s what we want to see!).

We walked the Anhinga Trail, named after the local bird, of which you can spot many perched in the scrubby trees, wings spread in their signature style as they try to dry off in the humid air before another dive for fish. We also saw turtles, various other bird species, and multiple gators literally chilling in the water, or maybe in this case warming in the water. Apparently gators have very specific temperature needs and even the warm, muggy morning of our visit was too cold for them!

There are many other trails in the same area, or if you have the time, you can continue further into the park to Shark Valley. Here, there is a longer trail for visitors (you’d need the whole day to walk the whole loop), and instead of walking safely above the gators in the water, you are quite literally on their level walking by their mud holes. Just don’t get too close!

I found the Everglades to be beautiful but also really depressing in a way. The visitors centers have a lot of information on the history of the area and how humans almost completely decimated this natural watershed in favor of draining land for farming, building, and more (including Disney World!). The natural aquifers have been disastrously affected, which is why Florida also has a high instance of spontaneous sinkholes occurring, which is one of the most terrifying things I’ve ever read about. Imagine sitting in your house and then suddenly being swallowed into the earth! Full body shudder. There are more conservation efforts now, but walking through the trails and contemplating the loss is a sobering experience for sure.

Homestead

Speaking of draining the Everglades, that’s exactly how the area around Homestead was settled, and transformed into farmlands. Today, Homestead sits on the edge of the Everglades, a farming community central to Florida’s agricultural industry, but also a popular layover spot for tourists heading into the park. If you are on a day trip from Miami or passing through on your way into the Everglades, there are places definitely worth stopping for!

Top Eats In and Around Homestead

Robert Is Here This place started as a small fruit stand and has morphed into a full roadside attraction, complete with petting zoo. You can buy all sorts of fresh produce here, but they are known for their fresh fruit milkshakes. I can attest the mango was pretty great, and they also sell pressed sandwiches, perfect food for filling up before heading into the Everglades. They also had boiled peanuts! If you know, you know.

Chefs on the Run We had dinner here, mostly because it was open fairly late and near to our hotel, but it turned out to be one of the biggest surprises of the whole trip! The food was phenomenal, actually, including their take on key lime pie, in an empanada form (key lime pie #3). It turned out the next table was another group traveling from the Bay Area, and we all agreed that this restaurant had food on par with the best of what you can find around here.

The Keys & Key West

You can drive the Keys in a day, or take your time working down the chain. Either way you do it, don’t miss some of the delightful attractions on the way to Key West. I’d say the Keys show off the downright weird and kooky side of Florida. The state is on the weirder side anyway, but the Keys have an energy all their own.

Key West

Aside from Disney World and Miami, Key West is probably the least undiscovered corner of Florida, I know. Yet I still liked it more than I thought I would! My main impression of it before the trip was as a party destination for spring breakers and parrot head boomers. It is that, quite proudly so, but it turns out that leaning all the way into that vibe is the best way to enjoy Key West.

I thought we’d mostly be using it as a home base for our trip to the Dry Tortugas, but from the first evening we arrived, I was all the way in on Key West. We walked by cute cottages on sleepy streets populated by wild roosters, down through the main drag of bars on Duvall Street, and out to an outdoor bar on a pier full of rainbow colored tables and umbrellas, with live music and a perfect view of the sunset. One hour into our time in Key West and I think I had my first real moment of “ah, I’m on vacation!”

We bar hopped around Duvall Street, taking in the various performances of live music, ranging from classic rock covers to pop songs performed on request. We learned that Key West is not open late for dinner, so plan accordingly if you are hungry.

We toured Hemingway’s house and admired the cats and all their extra toes. We (or mostly I) sampled multiple examples of the local dessert in both pie and ice cream forms. We sweat buckets, because Key West is basically in the Caribbean and it was hot! We ate fresh grilled fish within sight of the ocean and I learned that Florida has white sand beaches and turquoise water on par with the ritziest island getaways.

Key West isn’t exactly cheap, and it was probably the biggest splurge of our trip in terms of hotel prices, but if you are looking for a tropical vacation and you want to stay domestic, I think Key West is a pretty good option. It may be full of boomers, but sometimes your parents are right.

Top Key West Eats & Drinks

Southernmost Beach Cafe We arrived at this beachside cafe hot, sweaty and hangry. But with two seats in the shade, a couple of margaritas and fresh grilled fish, we were happy again. This casual restaurant is on the Southernmost Beach Resort property (across the street from the main resort), but is open to the public.

Louie’s Backyard When I had my solo dinner at Joe’s Stone Crab, I told my server I was heading to Key West and he jotted down a list of his favorite restaurants, and this was on it. Louie’s has a downstairs restaurant that requires reservations, but the upstairs accepts walk ins, and has tables set into the balcony if you are lucky enough to snag one, which we were! That means you can do what we did, and order multiple plates and drinks while you look out at the ocean view. And you’ll want to, the food and drinks were all terrific. There is also a large bar on the lower deck in back where you can wait for your table. And of course, there’s pie for dessert (key lime pie #4).

Blue Heaven This was another recommendation from my server at Joe’s. It’s most well known for brunch, where you can get standards like shrimp and grits and egg plates, and finish up with a slice of their famous key lime pie (everybody here has famous pie). The food was decent, though I question topping your signature pie with a mound of meringue in that particular climate (key lime pie #5)! The real star here is the ambience, complete with the ubiquitous roosters and outdoor patio seating centered around a massive bar serving up bloody marys and fresh juices.

Key West Key Lime Pie Co This was our very last stop on the way out of town, since I wanted to try their take on the local pie. Much like Blue Heaven, I’m skeptical of their chosen version given the climate of Key West. Here, it’s a no-bake version made with a condensed milk base that succumbs quickly to the heat. I tried to order a slice of pie, and when the woman at the counter asked if I was taking it to go and how long before I planned to eat it, she told me a slice would melt in 15 minutes, and steered me to ordering the mini cup version, and packed it up in a double bag of ice. Durability aside, it was pretty good! The pie had a nice, tart flavor, but was also pretty sweet, not surprising considering all that condensed milk (key lime pie #6).

Sunset Pier It’s almost not worth recommending bars in Key West, as there are so many and a walk down Duvall St. won’t steer you wrong (at the very least just follow the crowds into Sloppy Joe’s). But I loved this bar, especially at sunset, as the name implies.

Where to Stay in Key West

Like I said, Key West was one of the splurgier parts of our trip. Especially considering we stayed in Florida the week of President’s Day, it was pretty much peak season. Even so, we found a highly functional, well-located option at NYAH Key West, an adults-only place somewhere on the spectrum between budget hotel and hostel. You can get private rooms though, and ours had the best air-conditioning of the entire trip. There was also a free (bare-bones) breakfast and free coffee and tea in the lobby. Parking was on the street or in a nearby lot, but fairly easy to find.

Dry Tortugas

I hate to admit it after my gushing above, but we might have skipped Key West if not for the Dry Tortugas. It’s only accessible from Key West though, so if you want to go, Key West is part of the bargain (not like that’s a downside, though!).

I’d had this National Park on my list ever since I saw a random picture of it online a few years ago. Where was that??? As it turns, out, there’s an old, abandoned, Civil War-era fort/military prison off the coast of Florida, surrounded by turquoise water and white sand beaches. Our country’s history is so weird and interesting, sometimes, isn’t it?

I don’t think anyone actually ever held prisoner there would agree with me, but as a modern visitor, I found the Dry Tortugas to be delightful! It probably helped that we went in February, because it was very hot! This was the warmest day of the entire trip and we spent it on a desert island, basically. There is absolutely no shade outside the fort, and no running water, hence the “dry” in Dry Tortugas. But there is a little beach and you can swim or snorkel around the perimeter of the prison. I had an odd moment wondering what those people once held prisoner there would think if they knew that one day Americans would be taking day tours out to the island for recreation. They’d probably think we were all nuts.

But then again, they didn’t know about seaplanes!

Most visitors arrive at Dry Tortugas via the ferry, but if you favor aerial views, a shorter excursion, or if the ferry sells out before you remember to buy your tickets (ahem), you can also take a half-day or full-day trip to the island by seaplane. Neither option is exactly cheap, and the seaplane is definitely a splurge, but if you aren’t traveling with a large family or if you want to treat yourself to something fun, I highly recommend the seaplane option. The trip out to the island is 30 minutes, compared to the 2 hours by boat, and you get a great view along the way of Key West, outlying islands, shipwrecks, and even sea turtles and sharks. The trip also included snorkel gear and a cooler of drinks. The seaplane is also more flexible, as you can do a half-day trip, instead of full day, if you don’t want to commit an entire day to the experience.

The Keys

Key West might get most of the attention, but don’t sleep on the other Keys in the chain! To explore the Florida Keys, you can really only drive one road, Highway 1, and the peak speed is probably 45 mph. This makes for perfect lazy road tripping conditions, the kind of day where you cruise in the car and stop for anything that catches your eye.

Top Highlights of the Florida Keys

Robbie’s FEED THE TARPON! You’ll know what that means almost as soon as you arrive at Robbies, a road side collection of artist stands, restaurant, and the main attraction, feeding the tarpon. Buy a bucket of bait fish, and proceed onto the pier where you toss the smaller fish straight into the mouths of the massive tarpon. Take care to avoid the pelicans, who have caught on to this easy food source and are not shy about asserting their rights to the grub.

Rain Barrel Sculpture Gallery Any place signposted by a giant lobster does not want to be missed, and you shouldn’t let it be! This quirky collection of shops in Islamorada is a great stop to stretch your legs, poke around, and at minimum, admire the lobster.

Sombrero Beach This is the “lesser known” beach the park ranger at Biscayne Bay told us about. We arrived around mid-day to find the parking lot full and the beach crowded with people. But it was scenic, and a perfect spot to enjoy my cup o’ key lime pie.

Gulf Coast: Naples, Tampa & Weeki Wachee

So, there’s a really fun thing you might not know about Florida’s Gulf Coast, which is that they have mermaids!

Yes, really!

Actually, they have two kinds, the ones that used to trick sailors into thinking mermaids existed, and the Weeki Wachee kind, where women (and men!) don fish tails and perform underwater.

You see why I fell in love with Florida?

Naples

We headed to Naples after our stop in Shark Valley, and arrived in time for our boat tour of the canals, where manatees like to hang out in the brackish water. Manatees have basically no body fat, so they don’t come up to the surface except to breathe. They can hold their breath for a looong time, so you have to be on the alert for them! But when they do travel to the surface, it’s easy to understand why sailors, drunk on grog, may have thought they were seeing an exotic species of half fish/half human women dazzling them from the ocean’s depths. The tannic water gives them a golden hue, and their barnacled skin creates exotic visual patterns. It’s still quite a mental stretch to see a beautiful siren in all of that, but manatees are majestic in their way, even to more sober eyes.

Aside from the manatees, the boat tour also provided scenic views of the local mansions along the water and the edges of the mangrove swamps. That’s pretty much all we saw of Naples, but if you are headed along the gulf coast in either direction, it’s worth the stop for a boat ride.

Tampa & Weeki Wachee

Our main reason for heading to the gulf coast, and actually the kernel of the idea for this entire trip, were the other mermaids, at Weeki Wachee. I don’t exactly remember where I first heard or read that there was a theme park in Florida where people dress up as mermaids and mermen and perform underwater, breathing out of air hoses all the while, but once I had heard this, I kept encountering Weeki Wachee in pop culture, news articles, and while working in the travel industry. I knew I had to go one day, because the concept was so weird and wonderfully kitschy, how can you not try to witness it for yourself?

Luckily, Susan felt exactly the same way at the prospect of mermaids, so we headed up the coast to Tampa, and made the drive over to Weeki Wachee, anxiously watching the sky and the temperature on the way. The mermaids perform in a natural spring, so if the air temperature is too cold they won’t perform. And even though the rest of the trip had been as hot and humid as Florida is known for, once we hit Tampa we collided with a cold front that plummeted the temperature to 50 degrees. I went from sweating in shorts to bundling up in my winter coat overnight.

But we hit the minimum air temperature, and the mermaids went on! Given the weather, the park was pretty empty, so we had a front-row seat to the spectacle. I think Susan and I were both a little apprehensive that Weeki Wachee would be a let down, as we had built it up in our minds as this weird and wonderful end goal of the entire Florida trip, and what if it was just…bad? And true, the park is older, and it was a little sad looking, especially with the lack of visitors, but nothing about the mermaid show was a disappointment. Those women (and one man) are athletes, ok? They are basically performing a choreographed dance under water, moving through the water like it’s nothing, and also lip synching while trying not to drown. People should be lining up to see this! Maybe they are, in warmer weather? Anyway, once the curtain dropped, I turned to Susan and proclaimed, “that is one of the best things I have ever witnessed.” She agreed.

And if mermaids aren’t enough to interest you, especially given the nearby proximity of Disney World, just know that park admission to Weeki Wachee is only $13 and includes all three daily mermaid shows, the river cruise, animal show, and water park. The price alone made me feel like we had traveled back in time.

After Weeki Wachee, we had an evening in Tampa before we flew home the next day. It turns out Tampa has the longest continuous sidewalk in the world! So, of course we walked it. The walk had great views of the fancy homes on the water and the pelicans swooping and diving for fish. Everything was steely grey and overcast, but in sunny weather, I think I’d be envious of the people living there. Just after our trip Tom Brady announced he was leaving New England for Tampa Bay. Honestly? I get it.

Top Eats in Tampa and the Gulf Coast

Big Ray’s Fish Camp Tampa is known for the grouper sandwich, and so we headed to this place known for their version. This was probably one of my top 3 meals on the whole trip. The sandwiches are delicious, and massive, but you should also try the smoked fish dip and the deep fried key lime pie (key lime pie #7).

Cafe Soleil This was a random place we stopped at for breakfast in St. Petes, on the way to Weeki Wachee. It’s a simple French bakery, but the service was so friendly and the croissant sandwiches a must.

Dry Dock Waterfront Grill Another random pick for dinner for our quick stop overnight in Sarasota, between Naples and Tampa. As most restaurants in the area, the menu has a heavy focus on seafood, but when it’s all so fresh what else could you possibly want to order? The food and service were great here, though it was pretty busy so make a reservation or go early, if you can.