At Uproxx, we love a classic American summer road trip. The feeling of freedom as you roll down your windows and barrel down an unknown road – it’s truly intoxicating. This year, of course, some of those long-distance or cross-country trips have been tabled due to inflation and high fuel costs. But that doesn’t have to keep you off the road. Personally, I have been focusing on shorter-distance road trips – for cost concerns but also to experience each stop more fully.
Driving the Overseas Highway (Highway 1) south through the Florida Keys was the perfect summer “slow travel” road trip for me (it’s only 160 miles!). Consistently lauded as one of the most epic road trips in the United States, it certainly didn’t disappoint — with tons to do, some incredible food, and great properties to visit. Plus a whole lot of natural adventure.
Check my full guide below.
Start: Miami
I started my trek by flying into Miami on a redeye from Denver – but Fort Lauderdale is just as easy, depending on the price of flights and rental cars. Luckily, watching the sun come up from the air over Miami’s bustling coastline re-energized me for the full week ahead.
I didn’t stick around Miami for long, although you could easily stretch out your trip here with plenty of unique places to eat, drink, explore, and party. But I was more interested in the laid-back Florida Keys vibe, so I headed south.
Stop 1: Biscayne National Park
As you head towards the Overseas Highway, you’ll pass right by one of the lesser known and less visited major US National Parks – Biscayne National Park. It’s definitely worth a trip. Ninety-five percent of the park is water – protecting Biscayne Bay, a mangrove swamp, and offshore coral reefs. Spend some time here boating, fishing, diving, or on a guided tour before continuing on to the Keys.
I recommend reserving a cruise to Boca Chita Key and Lighthouse, at a minimum. If you’re daring, do some kiteboarding.
Stop 2: Key Largo
After checking another National Park off your list, continue on Highway 1 where you’ll soon enter the Florida Keys themselves. There are five main islands that make up the region from Key Largo to Key West (and on to Dry Tortugas beyond the highway), but hundreds of small islands on the archipelago.
I decided to make Key Largo my home base for a couple of days of exploration, as it is the first of the main keys on the overseas highway. From here you can explore the upper keys easily before heading down further south.
Stay:
I stayed at Bakers Cay Resort on the Gulf side of Key Largo. Just a quick turn off Highway 1 and I was transported into a chic tropical paradise. The view from my room was serene, but I could easily head to the beach area for a more lively vibe. I really loved the hammock beach area with chairs under the mangroves for watching the sunset and enjoying a drink.
Eat:
I didn’t eat many meals in Key Largo itself, but I loved brunch at Key Largo Conch House where I enjoyed key lime pancakes (you’ll start to notice a theme).
Drink:
Dry Rocks is the place to see and be seen in Key Largo – and luckily it was right at my hotel. I enjoyed a simple glass of rose, but the margaritas and tequila flights looked like the perfect island thirst quenchers.
Explore:
John Pennekamp Coral Reef State Park is located on Key Largo, and the area is known to be the “dive capital of the world.” With easy access to many dive sites and the prime location on the 3rd largest barrier reef in the world, you can’t visit without getting underwater. Whether snorkeling or scuba – you can’t go wrong.
Stop 3: Islamorada
My next stop was a day spent in Islamorada, just a 20-minute drive from my home base in Key Largo. Also known for watersports, I was looking forward to some time in the water.
Explore:
I spent the morning SNUBA and snorkeling with Sundance Watersports out of Robbie’s Marina. And yes, you read that right – Snuba, not scuba. Snuba is a cross between scuba and snorkeling – with surface-supplied oxygen enabling you to dive deeper into the water – 20 ft – than snorkeling, but without a personal tank and certifications necessary for SCUBA.
I was nervous at first, to be honest, without any diving experience under my belt, but once I was in the water it felt completely natural. We spent time diving around a reef, seeing a large array of fish and even a sea turtles. I definitely recommend it.
Eat:
I had a day of great meals in Islamorada, starting with The Hungry Tarpon at Robbie’s Marina. I got there right after opening, as it can become very crowded (which I witnessed firsthand later on) and I was rewarded with a great table and better service. I had the Purple Isle, a crepe filled with lobster meat and topped with hollandaise. It was as rich and tasty as you’re imagining.
For lunch, I stopped by Bad Boy Burrito, a local favorite Mexican spot. Tucked away and unassuming, Bad Boy Burrito prides itself on local, fresh and organic ingredients – and it was evident in my lunch. I had the key west pink shrimp burrito and must have downed it without ever putting it down once – it was that good.
For dinner, I went slightly more upscale with a meal at Morada Bay Beach Cafe. It gave Bloodline vibes (which was filmed nearby) in the best way, with tables set right on the sand and the perfect sunset view. I enjoyed the nightly special – wahoo – and a side of lobster tail (not a sentence I can say very often). Of course, I ended my meal with key lime pie while watching the sunset.
It felt like a dream come to life.
Drink:
Before dinner, I stopped by Florida Keys Brewing, the first microbrewery in the Upper Keys. I was lucky to get a tour and I was as enchanted with their story as I was with the beer. The vibe is everything you’d want in a tropical brewery, complete with live music, a food truck, local art, and even brewery cats.
I enjoyed a flight of beer that included the famous Iguana Bait – a Kolsch brewed with hibiscus and honey — and nearly missed my dinner reservation while enjoying the friendly local scene.
Stop 4: Marathon
The next morning I checked out of Bakers Cay and headed south to Marathon with just one thing on the agenda – the Turtle Hospital. Located on the grounds of an old roadside motel, the Turtle Hospital is a non-profit committed to rescuing, rehabbing, and releasing sea turtles (when possible). I loved taking a tour and learning all that the hospital does for these majestic animals.
Stop 5: Key West
My last stop was Key West – the southernmost point of not just the Florida Keys, but the continental United States. Famously located closer to Cuba than Miami, the history of Key West is legendary. At one point the wealthiest city in the United States, it is still known to be eclectic and full of surprises. You could spend days just exploring this small, historic town.
Stay:
I stayed at Parrot Key Hotel & Villas which was peaceful and upscale, located just outside the hustle and bustle of the old town area. The Hotel has four pools, a bar and restaurant, and a quaint garden vibe. I had a room overlooking the water and loved waking up to the towering palms outside. I actually ended up dropping my rental car off at the airport early once I arrived in Key West, utilizing the hotel shuttle and a few ride shares.
Parking in Key West is difficult (and expensive) so shuttles, walking, scooters, bikes, or ride shares are definitely the way to go.
Eat:
I had a lot of memorable meals in Key West – beyond just the key lime pie on a stick. I liked The Docks Restaurant and Raw Bar most during my stay. Located on the nearby Stock Island, The Docks has a great secret feel on, well, the docks, with a great bar and – of course – raw bar. I enjoyed a rose sangria, shrimp cocktail, and the Local Sauteed Snapper. The snapper was incredible, with a green gazpacho risotto and key lime bure blanc.
Other meals I won’t forget were dinner at Half Shell Raw Bar and brunch at Blue Heaven.
Drink:
Key West is known as a party and festival town, and there is no shortage of bars to help you enjoy it. I didn’t spend too much time on Duval Street – the main drag for bars, restaurants, and shops — but I did stop in to Sloppy Joes, Ernest Hemingway’s favorite hangout during his time in Key West, for a refreshing drink and some live music.
Explore:
There is seemingly no end to exploration in Key West. From the water to the city, it has something for everyone. I loved spending a day with Honest Eco Tours snorkeling, kayaking, and dolphin watching – all while learning about the ecosystem and sustainability measures that are being taken in the area and by the company themselves. Honest Eco Tours is a unique tour company in that they aim to educate as well as give patrons a great experience. Builders of the first Lithium-Ion hybrid Electric boat for Charter in United States, Honest Eco takes conservation seriously – and provides a great day on the water.
It would be a shame to visit Key West without taking a Sunset Sail. As the southernmost point of the continental United States, the sunsets are legendary – and so are the sails. I boarded a boat with Sebago Watersports for music, open bar, and apps while cruising around the island and watching a gorgeous sunset.
Once you’re back on land you’ll want to spend time in Old Town and Duval St. As the historic district, I could walk around looking at the homes and visiting museums all day. I loved visiting the Ernest Hemingway Home and Museum, learning more about the iconic author’s life in Key West while scouting for the famous polydactyl cats. I also loved visiting Truman’s Little White House, the Key West Butterfly and Nature Conservatory, and, of course, the Southernmost Point.
Bonus:
Your road trip might be over, but your adventure doesn’t have to be. A great day trip from Key West is to Dry Tortugas National Park and the ferry leaves right from downtown. It is a once-in-a-lifetime bucket list national park trip, and I can’t recommend experiencing it for yourself enough.