The drive from Miami to Key West is one of the most famous road trips in America. Stretching about 160 miles through the Florida Keys, the route follows the scenic Overseas Highway, hopping from island to island across dozens of bridges surrounded by turquoise water.
Of course, our goal wasn’t simply to get to Key West.
Our goal was to stop at every ridiculous tourist attraction we could find along the way.
And Florida did not disappoint.
This roatrip was also the first time we used the app called Guide Along, which is an app that automatically narrates cool stories and historical facts when your phone GPS detects each important location. It really kept us interested in the drive!
Stop #1: Robert Is Here
Our first stop was the legendary Robert Is Here Fruit Stand in Homestead.
At first glance, it looks like a simple roadside fruit market. It is not.
This place has been operating since 1959 and has become one of South Florida’s most famous roadside attractions. The market specializes in exotic fruits from around the world, many of which most visitors have never heard of. The famous man, Robert, is here in the pink shirt helping customers.
Where else can you casually buy things like, Mamey, Jackfruit, Dragon Fruit, Sapodilla, Sour Sop, Emu eggs, etc..
The property also includes a small petting zoo behind the market, making it a fun stop for families.
While waiting for Tania and Lauren to catch up, we grabbed one of their famous milkshakes made from fresh Mamey fruit. If you’ve never had Mamey before, imagine a rich, creamy blend of baked sweet potato, pumpkin pie, caramel, and almond flavors. Its delicious.
Stop #2: The World’s Largest Lobster
Next up was one of Florida’s finest contributions to roadside architecture: The giant lobster.
Located at Rain Barrel Village, this massive sculpture named “Betsy” claims the title of one of the largest lobster sculptures in the world.
Because if you’re driving through the Keys and suddenly think, “You know what this trip is missing? A giant crustacean,” Florida has your back.
The sculpture stands over 30 feet tall and has become one of the most photographed landmarks in the Keys.
We snapped our obligatory photos and explored a few of the quirky art shops nearby before continuing south.
Stop #3: Key Lime Pie Research
A road trip through the Florida Keys requires scientific testing. Specifically, key lime pie testing.
Our next stop was the famous Key Lime Factory Store Products in Tavernier. Not much of a factory, at least nothign we could see besides a store selling every configuration of key lime pie food. Cookies, candies, merengues, etc…
For those unfamiliar, Key Lime Pie was invented in the Florida Keys and remains the region’s most iconic dessert. Traditional Key Lime Pie is made with: Key lime juice, Egg yolk, Sweetened condensed milk, and Graham cracker crust. Simple and perfect.
Dangerously easy to eat.
We shared a pie in their backyard seating area and officially began our completely unbiased search for the best Key Lime Pie in the Keys. Purely for research purposes, of course. This pie was going to be one of the best we tried.
Stop #4: Robbie’s and the Battle of the Pelicans
Our next destination was the famous Robbie’s of Islamorada. If you’ve ever seen photos of giant fish leaping out of the water to eat from people’s hands, this is probably where they were taken.
Robbie’s is famous for its tarpon feeding experience. Here’s how it works: You buy a bucket of fish, you walk onto a dock, you attempt to feed a tarpon, you quickly realize the real challenge isn’t the tarpon, it’s the pelicans.
These birds have spent years perfecting the art of fish theft. They circle overhead waiting for tourists to make mistakes.
While everyone else carefully evaluated their life choices, Eitan volunteered as tribute.
Holding a fish over the water while a giant tarpon slowly approaches is surprisingly nerve-racking. The fish can grow over six feet long and weigh more than 200 pounds. But Eitan was not going to back down, as he is our bravest warrior.
Eventually one launched itself out of the water and grabbed the fish, and possibly part of Eitan’s soul.
Definitely one of the most memorable stops of the trip.
Stop #5: The Seven Mile Bridge
Continuing south, we eventually reached the iconic Seven Mile Bridge.
This bridge is one of the most recognizable landmarks in the Florida Keys and connects Knight’s Key to Little Duck Key. Stretching across open ocean, the views are spectacular in every direction.
The current bridge was completed in 1982, but trunning alongside the modern bridge is the remains of the original Overseas Railroad, one of the most ambitious engineering projects in American history.
Built by industrialist Henry Flagler and completed in 1912, the railroad connected mainland Florida to Key West by crossing more than 100 miles of open water through a series of bridges and viaducts. Known as the “Eighth Wonder of the World,” it allowed passengers to travel by train all the way from New York to Key West.
The railroad was heavily damaged by a devastating hurricane in 1935, and many of its bridges were later incorporated into what is now the Overseas Highway. Looking at the old bridge stretching across the turquoise water, it’s hard not to appreciate the incredible engineering achievement it represented over a century ago.
There is a little train that takes you around, but we were not there at the specific departure times, so we just walked a portion of the pedestrian path and admired the endless blue water surrounding us. It’s one of those places where photos don’t quite capture how impressive it feels in person.
Arrival in Key West
Eventually we reached our hotel in Key West and checked in.
After a short break to cool off and recharge, we took the shuttle into downtown Key West to meet up with the rest of our friends.
The atmosphere downtown was energetic, lively, and very, very touristy.
Soon we found ourselves joining several thousand other people gathered at the famous Mallory Square sunset celebration.
The Famous Key West Sunset
Every evening, crowds gather at Mallory Square to watch the sun disappear into the Gulf of Mexico.
Street performers entertain the crowds while vendors sell drinks, souvenirs, artwork, and just about everything else imaginable.
The sunset was beautiful. But if I’m being honest? We’ve seen plenty of amazing sunsets around the world, and this one didn’t quite make the all-time list.
The real entertainment was watching the people.
The square felt like a giant outdoor festival with musicians, performers, artists, and enough frozen cocktails to keep the local economy thriving.
It was also our first indication of what Key West’s tourist scene would be like. Let’s just say “classy tropical paradise” wasn’t the dominant vibe.
While most of our group headed toward Duval Street, Ariela and Eitan became completely distracted by one of the street performers. A guy performing tricks with giant whips.
As any responsible parent would do, we stopped everything and watched. Because giant whips are objectively more interesting than shopping. But not worry, we still did some window shopping after:
Dinner and the Mystery of the Spicy Pasta
Eventually we wandered down famous Duval Street searching for dinner. After passing countless bars, souvenir shops, and tourists carrying drinks in containers the size of small buckets, we found a beautiful restaurant with outdoor seating. Everything seemed perfect, but then the food arrived.
Sarah ordered a Key Lime Martini. Unfortunately, it tasted like someone blended a margarita with furniture polish. Not recommended.
Meanwhile, Eitan ordered a pasta dish. The menu gave absolutely no indication that it would be this spicy. Yet somehow the chef delivered something that felt equivalent to a Level 10 Thai curry challenge.
Every bite raised new questions. Was this a mistake? Did the chef confuse our table with someone else’s? Did I unknowingly offend the waitress? We’ll never know.
What we do know is that Eitan bravely battled through approximately half the plate before admitting defeat.
We also tried conch fritters, which some people seemed to like.
We then walked to the shuttle stop to wait for the last shuttle of the night that would bring us back to our hotel for a well deserve night’s sleep.
The next day we will be exploring all the sights in Key West!
Bonus pic of the day:
I didnt know if people here were on board of changing the name of the Gulf of Mexico to the Gulf of America. I got my answer pretty quickly:
