Chasing Sunsets from Miami to Key West
When it comes to bucket list scenic drives in the US, there’s some pretty stiff competition. I’ve been working my way through the country’s “must-do” road trips for at least a decade now, and despite having crossed from America’s east to west coasts a few times, I still feel I’m only just getting started.
While my top three scenic drives include Route 66, the southern rim of the Grand Canyon, and Virginia’s epic Skyline Drive, they certainly met their match when my wife and I decided that Florida’s Overseas Highway should be a priority. And what a drive it was.
On a journey of 159 miles, including the stretch from Miami to Key Largo (the Overseas Highway itself encompasses 113 miles of that total), we were staggered to learn we would not only cross 42 bridges, the most impressive of which is seven miles long, but we’d also cross 44 islands, all of them tropical. Oh boy, were we excited, especially as we knew we were also going to see some of the best sunsets anywhere in the world when we arrived in Key West, the continental USA’s southernmost city?
Start Your Adventure With a Miami Sunset
While it’s only a four-hour drive from Miami to Key West without stops, we knew that this was one trip we wanted to take slowly. So slowly, in fact, that we planned on breaking it up with a stay in Marathon, about two-thirds of the way along what we were soon to learn is Florida’s most unique tourist route.
Miami traffic can be pretty horrendous at the best of times, so after witnessing a spectacular sunset from our son’s apartment in Brickell (a taste of what was to come), we retreated to our accommodations at Hotel Greystone in Miami Beach in readiness for an early departure to beat the traffic.
And it worked. Even though traffic was getting heavy as we skirted downtown Miami at around 6 am, we reached Homestead and Florida City, the last two mainland communities on our epic drive to Key West, in around 50 minutes. Our first proper stop? That was to be Key Largo, 30 minutes from our coffee pick-up in Homestead and a destination forever immortalized by the Beach Boys in their hit, Kokomo.
Take a Break in Key Largo and Tavernier
While the 30-minute drive from Homestead to the official start of the Overseas Highway in the northern extremities of Key Largo is nothing to write home about, by the time we crossed that first bridge over Manatee Creek, we were definitely pumped for the adventure that lay ahead.
Our first stop was John Pennekamp Coral Reef State Park, one of the top attractions in the Florida Keys. Set overlooking the Keys’ Atlantic coastline (the other side faces the Gulf of Mexico), our $8 admission (per car) provided access to the visitor center, a great place to start for its educational displays and aquarium with local marine life.
Other amenities include clean washrooms and showers, picnic spots, and access to a number of beaches, the closest to the parking area being Cannon Beach, named after the old weaponry, dotted about. While we stuck to land, the park is of course famous for its snorkelling, with equipment rentals available. Other on-water fun includes kayak and paddleboard rentals, as well as tours over the reef in a glass bottom boat.
Refreshed after a walk and dipping our toes, we headed south for 20 minutes to what we’d heard was one of the best beaches in the Keys and a great spot for the morning snacks we’d packed: Harry Harris Park. Although man-made (many along the Overseas Highway are), it was clean and very quiet when we arrived, something that isn’t typical of Florida beaches unless you arrive early or later in the day for those spectacular Gulf sunsets.
Fun Things To Do In Islamorada
True to our vow to “take our time,” we knew our next stop, Islamorada, was going to be a longer one. There were three attractions we wanted to see here (there are, of course, many more), even if it meant just a quick look-see. The first, the Theater of the Sea, was where we’d chosen to spend the most time, and arriving before lunch meant we could spend at least a few hours there. And we’re glad we did, especially for its amazing Sea Turtle Experience, a unique chance to interact with some of the deep sea’s most fascinating creatures.
Having spent a little longer than anticipated at Theater of the Sea, making sure we also saw its sea lion and dolphin shows, it was a quick visit to the History of Diving Museum to learn more about diving in the Florida Keys. This was followed by an all-too-brief stop at Windley Key Fossil Reef Geological State Park, a now abandoned quarry where a unique and no-longer submerged coral reef can be seen.
A Marathon of Sunsets
The next leg of our journey, from Islamorada to Marathon, was the most incredible part of the trip so far in terms of scenery. Here, we stopped before crossing Indian Channel Bridge, one of the longest we’d seen so far, to marvel at the views. There’s ample parking at each end of the bridge, so if you miss it before crossing, you can easily pull over once across. Just knowing we were standing at a point overlooking both the Gulf of Mexico and the Atlantic, which meet up here, was remarkable. This was also the first place where we got an up-close look at those bright-green iguanas that seemed to be everywhere in the Keys (they’re an invasive species, so don’t feed them).
From here until Marathon, we found ourselves stopping frequently to admire similar spectacular views over the water. Favorites included the parking area before crossing Channel #2 where you can see a section of the original Overseas Railroad running adjacent the modern bridge. Now part of the Florida Keys Overseas Heritage Trail, a planned 106-mile paved trail connecting Key Largo to Key West that’s only 16 miles shy of being completed, this bike and pedestrian route is also popular with fishing fans. Another highlight of this leg of the journey was a stop at Long Key State Park, a 965-acre property with a stunning shoreline overlooking the Atlantic.
Our final stop for this leg of the journey was Marathon. And here’s where we cheated a little. As timeshare owners (that’s a story for another day), we’d managed to secure an exchange at Tranquility Bay Beach Resort, a 4-star property on the Overseas Highway with spectacular views over the Gulf. Best of all, it served as a great base from which to explore top Marathon attractions like the Turtle Hospital, which rescues and rehabilitates these creatures to the wild, and the wonderful Dolphin Research Center, where you can get up close with dolphins in a safe and ethically run facility where these creatures aren’t forced to do tricks, but instead are allowed to be themselves. A truly fascinating experience.
Marathon is also where we got our first glimpse of the Old Seven Mile Bridge, built between 1909 and 1912 as part of the original Overseas Railroad. Considered an engineering marvel at the time (it still is), it connected mainland Florida to Key West, overcoming the challenge of spanning miles of open water, just as the Overseas Highway does today. Made obsolete by a hurricane in1935, parts of the railway line were repurposed for the highway, while the portion known as Old Seven Mile Bridge, or the "Old Seven," was made into a fantastic pedestrian and bike path that’s also popular with fisherfolk.
We were also treated to some spectacular sunsets in Marathon, with the resort’s private beach and breakwater making for a stunning backdrop. And so, refreshed after our break, we were ready to tackle the final 50 miles of our drive from Marathon to Key West.
Those Spectacular Key West Sunsets
Driving across the new Seven Mile Bridge was definitely one of the highlights of our Miami to Key West adventure. It’s even more incredible when you realize you’re over water the entirety of the way, something that’s clear as you glance at your GPS and see nothing but blue on the screen. To really appreciate it, do as we did and stop at the parking lot immediately when you hit land again at Little Duck Key Wayside Park, where you can get a great view of both the new and the old bridges.
Just a few miles further along the highway, you’ll come to Bahia Honda State Park. It’s worth squeezing in a stop here to walk to the old Bahia Honda Railroad Bridge, a steel section of the Overseas Railroad that makes for a stunning backdrop. While only a very short portion of the bridge can be accessed, it’s definitely worth seeing.
After a great seafood lunch at Hogfish Bar & Grill on Stock Island, we were now ready to hit Key West, our final destination and quite literally the end of the highway. An easy 10-minute drive from the restaurant, we arrived in plenty of time to check into the Coconut Beach Resort before our first-ever Key West sunset.
We, in fact, stayed long enough in Key West to explore pretty much the whole of this fascinating town (you can read my account of that adventure in An Unforgettable Journey Through Florida's Key West). And yes, no matter where we chose to view a sunset, they were always amazing.
While the sunsets at Mallory Square at the top end of Duval Street, Key West’s lively main drag, were incredibly fun thanks to the crowds, our favorite were the altogether quieter experiences we enjoyed at the south side overlooking the Atlantic. Standing on the break wall near our resort, we seemed to have the whole of this amazing place to ourselves as we watched the sunset over the Southernmost Point Of The Continental US, just a few hundred yards away. As my wife so simply put, quoting her Scottish father… “Magic.” And she was right. It was a truly magical moment.
The Bottom Line
There’s little doubt that the 113-mile-long Overseas Highway (US1) is one of the most incredible drives in the United States and is definitely bucket list worthy. While it can be done in four hours (plus four hours back), I strongly urge you to break your journey up with at least a one-night stay in order to see everything there is to do in the Florida Keys.
Also, if at all possible, avoid weekends if you can, as Key West has become a very popular party destination. Not only does the Overseas Highway get busy, but Key West can be jammed as many revelers will fly in for fun. Parking in Key West can also be difficult, so leave your car at one of the many municipal lots on the edge of town and make use of the free bus service. It’ll get you to all the fun and back relatively quickly. And hey, after all that driving, you’ll no doubt be glad to leave the car somewhere safe while you get out and explore.
Finally, be sure to make a note of some of the other great spots to catch a sunset in Key West. Here are a few that we sampled and can thoroughly recommend:
Mallory Square: Famous for its iconic nightly Sunset Celebration, Mallory Square at the top (north) end of Duval Street is a lively spot featuring street performers, artisans, and food vendors. Arrive early to claim a spot along the waterfront for unobstructed views of the sun sinking into the Gulf of Mexico.
Fort Zachary Taylor Historic State Park: Just a short distance west of Duval (but close enough that you can walk there), this state park offers a more tranquil setting with stunning views of the sunset and plenty of parking. The beach area provides a great vantage point, and the silhouettes of palm trees and historic fortifications certainly add to the atmosphere.
Sunset Pier: Located at Ocean Key Resort, not far from Mallory Square, this colorful pier bar is a great spot to enjoy the sunset with a cocktail in hand. It’s less crowded with equally breathtaking views, but you’ll need to buy a drink or two (hey, it’s Key West, remember, so that’s what you’re here for anyway).
Take a Sunset Cruise: Why not splash out a little and opt for a sunset cruise from the harbor for a unique perspective? Catamarans and schooners provide a lovely way to watch the sky transform over the water, with some cruises offering fun wine tasting experiences.
White Street Pier: Also known as the Edward B. Knight Pier, this spot extends far into the water on the south side of town, making it a peaceful location to watch the sunset away from the crowds. Even if you don’t enjoy the views from the pier, it makes a stunning backdrop as the sun sets behind it.
Higgs Beach: Also located at the south end of Duval, this lovely beach provides a great place to enjoy a sunset if you’re traveling with kids as it’s generally quieter and there’s a children’s playground.
