Road Trip Notes // The Florida Keys
THE FLORIDA KEYS // the ultimate hideout for year-round travel. Above, Bahia Honda State Park.
If you’re looking to run away from life for a few days, you’ve come to the right place. However familiar you are with the culture in the unique but never boring state of Florida, I can promise you the locals don’t mind whatever you’re running from. Most will run to Miami, but after you’ve enjoyed all the food and nightlife you can stand - point South down the Overseas Highway. The string of islands that lie ahead are as diverse as you could draw up.
The Keys are steeped in history, extending back to the indigenous peoples and early Spanish explorers. These islands were first spotted by European eyes when Spanish explorer Juan Ponce de León encountered them in 1513 during his quest for the Fountain of Youth. Over the hundreds of years that followed, the Keys became a strategic maritime asset.
There were comings and goings of Spanish galleons laden with New World treasures, but tragically you’ll have to keep looking for endless youth. By the 19th century, the Keys had evolved into a string of towns known for fishing, sponging and notably - salvaging wealth from the numerous area shipwrecks. That practice earned Key West a title among the richest cities per capita in the United States at the time.
The 20th century was build on big dreams and bigger tragedies. The completion of the Overseas Railroad in 1912 was a remarkable engineering feat by Standard Oil magnate Henry Flagler and became known as the "Eighth Wonder of the World". It was a transformative idea at the time, connecting the once-isolated islands to mainland Florida and paving the way for economic and tourism growth. Tragically, the Labor Day Hurricane of 1935 devastated this lifeline. Hundreds were killed, including many World War I veterans working on highway projects. Miles of the Overseas Railroad, totally obliterated. The Florida state government stepped in, purchasing the easement rights from the railroad alongside the bridges that survived the storm. In 1938, the Overseas Highway opened - running from Miami to Key West. Most of it, laid directly on top of the old rail bed. Several of Flagler’s original concrete viaducts were converted into two-lane highway bridges still in use today.
Set the GPS to HYW 1 and start your Key’s journey arriving first on Key Largo. We spent a unique evening here truck camping without AC a few years ago. Aside from the smell, which was vast from the near endless mangroves our campsite was perched in - all we did in Key Largo was listen to The Beach Boys and consume strong drinks hoping to forget our sense of smell. I’m not knocking the island, we just had a bad site. One thing you’ll quickly learn if camping through the Key’s - land is at a premium.
Before continuing south from Key Largo, stop at Snooks Bayside for a lunch of Ahi Tuna by the water. With a little creativity in their extended lot, we parked the 42” truck & airstream combo without a problem. Important, as it’s unlikely you’ve dropped whatever you’re towing this far North on the road trip. As you continue South through Islamorada, enjoy the island where most of the real paper is stored in the form of private homes. I would use these Northern islands to stock up on any supplies you need for your trip. Florida strikes again - with Publix you’ll find ready to take your money on Key Largo, Islamorada, Marathon and Key West proper. If you’re towing a travel trailer or fifth-wheel, parking only get’s tighter the further South you drive. Take the grocery and fuel wins where you can find them.
By the time you hit Marathon a whole host of opportunities open up. A hub for fishing and diving trips, most of the full-time locals that work throughout the keys islands live here. Marathon is simply our favorite island in the Key’s. There’s a world famous Sea Turtle Hospital that’s worth your time before heading across the street to one of my favorite restaurants in the country - Burdines Waterfront.
Burdine’s Waterfront, Marathon // there may be no better set of GPS coordinates in the Key’s for drinking a very cold Corona right on the water. Built above a marina gas station, the atmosphere is all you’ve been looking for.
If you need respite from days of camping, Marathon also holds Isla Bella Resort. Opened in 2020 after Cat. IV Hurricane Irma (2017) took out the trailer park neighborhood that once stood in its place. Taking a short walk around is all you’ll need to start checking prices on HotelTonight & Booking.com.
We spent Thanksgiving week here during COVID in 2020 and if you need a base to book a guided fishing or dive trip from, this is where you want to run your credit card and sleep for a few nights.
From Marathon, head south down to Bahia Honda State Park for some of the most stunning beaches in the keys. There’s a day use area with full ocean access along with walking trails to explore the area. The park is a pristine natural paradise that offers the perfect blend of history and scenery. One of the park's most fascinating features is the old Seven Mile Bridge, part of Henry Flagler’s ambitious Overseas Railroad that connected the Keys to the mainland in the early 20th century.
This historic bridge, a marvel of its time, now stands partially as a pedestrian walkway, offering the chance to walk around and directly underneath the historic rail bridge. Take a small camp chair from the car and on a day when the beach is full and BBQ areas are long staked out and cooking, you can set up nearly anywhere you find shade. We sat for a while directly under the bridge, some of the only shade we could find on a hot September day. The beaches themselves are ready if the clear waters call for snorkeling, swimming and kayaking for those of us addicted to outdoor activities.
How it started, how it’s going // On left, the original Overseas Railroad, hurricane whipped but still standing. On right, your only tarmac this deep in the gulf - the Overseas Highway. A day or even a few hours stop at Bahia Honda State Park is a must. If you’re lucky enough to win the Powerball, you might have a chance to book a campsite six months out.
As you inevitably make your way South to Key West, make a pitstop on Stock Island. The Perry Hotel is the* choice if you’re not camping. Surrounded by boats of all kinds located right on the edge of a marina, it has epic seafood (Hogfish Bar & Grill) right next door and is a little bit further away from the crazy that is Duvall street and mainland Key West.
When you’re ready for Key West proper, my first stop for you is the historic Hemingway House. It really doesn’t matter if you love or hate his writing, the house is downright iconic. For $19 (kids are $7, 5 and under free) there are few more enjoyable ways to spend an hour on the island. There’s a reader’s dream bookstore onsite and once you dig into the history of old Ernest’s, eh… lifestyle in Key West, it’s hard not to have a laugh.
My favorite part of the house is the insanely decorative urinal he drug back from Sloppy Joe’s one drunken evening which his wife converted into a lovely garden piece you can still see in the backyard today.
Hemingway’s Office // Like an icon frozen in time, Hemingway finished A Farewell To Arms here in the early mornings of 1928. His time in the afternoons was designated to “exploring his surroundings” (drinking).
Duval Street: The origin of island madness
Duval Street is the legendary, perhaps infamous heart of Key West. Filled with eclectic shops (head turning at best, confusing and original), art galleries, restaurants and bars, this is the main drag in town. As you work your way down this famed street on foot (better after a strong drink), you will quickly realize this doesn’t feel like the rest of Florida. Each establishment - from the smallest art studio to the liveliest bar, is a weird part of the islands party of one identity. Make it a bar crawl and start early in the afternoon. Duvall st. is one of those places you don’t want to hang out in the AM hours (saftey).
No visit to the Keys is complete without a stop at Sloppy Joe's on Duval. This iconic bar, a favorite of Hemingway, would be a mistake to miss. Famous for its live music and vibrant atmosphere - Sloppy Joe's is one block from the water. Every time I’ve been there, live music is blaring and drinks are ice cold. Plenty of tourist’s sure, but a hell of a way to spend an afternoon. Plenty of locals hang out (and drink a lot of cheap beer) here, so don’t think you’re only visiting a tourist trap exclusively. Once you sit down at the bar, you’ll understand why.
President Truman’s Limousine // The 1949 Lincoln Cosmopolitan stretch. You may be wondering, where’s the Cadillac? Turns out, General Motors doubted Truman would win the election, so Ford stepped in with an instant classic saving the day. The roof was reinforced with Kevlar, a cutting-edge safety feature at the time.
Truman considered the Little White House more of a hideaway than a vacation spot. He spent six months here between 1946-1952, having first arrived in November 1946 on the advice of Fleet Admiral Chester Nimitz. Naval Air Station Key West was selected for some R&R while Truman was working to recover from illness and exhaustion. It was there Truman established The Little White House.
His morning routine was known to consist of a shot of bourbon and a glass of orange juice. “The only thing…different from the White House is just the change of scenery.” Truman told reporters in 1948. “We have direct wires… and I get a pouch nearly every day, and sign just as many documents and make just as many decisions as if I were sitting at the desk in the Executive Office.”
You don’t have to know much about Truman’s presidency to understand why he would seek solace and some change of landscape in Key West. If you can make it to the Little White House, you only need an hour or so to explore the grounds and tour the home.
It would be a mistake not to mention the pristine Dry Tortugas National Park. One of the more isolated parks on the NPS list, it’s located approximately 70 miles west of Key West. Accessible by boat or seaplane, the park comprises seven small islands and is renowned for its famous centerpiece, Fort Jefferson - one of the largest 19th-century American forts. Built to protect one of the most strategic deepwater anchorages in North America, you can spend the day touring the fort and surrounding area before either tent camping (info linked here) or returning back to Key West that afternoon.
This visually stunning and isolated National Park is on our list, but despite a dozen trips to the Key’s, I haven’t yet crossed it off the list. If you’re planning a trip down here, I wouldn’t go home without visiting. It’s logistically complicated to get to, but you have to take a day in your schedule and just make it happen. Use my regret to fuel your purchase! Hopefully I can update with more Dry Tortugas content in the coming year.
Camping in the Keys // Looking for the best in campsite reviews from someone who’s actually been there before? Look no further than the Travel Library for exact GPS coordinates and an always growing database of member’s-only editorial content.
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