海角社区

Overseas highway to Key West island, Florida Keys, USA.

Chasing Sunsets from Miami to Key West

When it comes to bucket list scenic drives in the US, there鈥檚 some pretty stiff competition. I鈥檝e been working my way through the country鈥檚 鈥渕ust-do鈥 road trips for at least a decade now, and despite having crossed from America鈥檚 east to west coasts a few times, I still feel I鈥檓 only just getting started.

While my top three scenic drives include Route 66, the southern rim of the Grand Canyon, and Virginia鈥檚 epic Skyline Drive, they certainly met their match when my wife and I decided that Florida鈥檚 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鈥檇 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 海角社区 when we arrived in Key West, the continental USA鈥檚 southernmost city?

Start Your Adventure With a Miami Sunset

Miami Sunset  by Bryan Dearsley - From Miami to Key West
Miami makes a wonderful starting point for an epic road trip to Key West (Photo: Bryan Dearsley)

While it鈥檚 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鈥檚 most unique tourist route.

Miami traffic can be pretty horrendous at the best of times, so after witnessing a spectacular sunset from our son鈥檚 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

John Pennekamp Coral Reef State Park Key Largo view from beach
John Pennekamp Coral Reef State Park makes a great first stop in Key Largo (Phot: Bryan Dearsley)

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鈥 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.

Harry Harris Park Tavernier
Tavernier's Harry Harris Park is a popular beach area and picnic spot in the Upper Keys (Photo: Bryan Dearsley)

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鈥檇 heard was one of the best beaches in the Keys and a great spot for the morning snacks we鈥檇 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鈥檛 typical of Florida beaches unless you arrive early or later in the day for those spectacular Gulf sunsets.

Fun Things To Do In Islamorada

The History of Diving Museum on the road from Miami to Key West - Photo Bryan Ddearsley
The History of Diving Museum is a worthwhile stop in Islamorada (Photo: Bryan Ddearsley)

True to our vow to 鈥渢ake our time,鈥 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鈥檇 chosen to spend the most time, and arriving before lunch meant we could spend at least a few hours there. And we鈥檙e glad we did, especially for its amazing Sea Turtle Experience, a unique chance to interact with some of the deep sea鈥檚 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 History of Diving Museum on the road from Miami to Key West - Photo Bryan Ddearsley
The sunsets at Tranquility Bay Beach Resort lived up to the name (Photo: Bryan Dearsley)

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鈥檇 seen so far, to marvel at the views. There鈥檚 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鈥檙e an invasive species, so don鈥檛 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鈥檚 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.

Rescued dolphons at the Dolphon Research Center in Marathon Photo by Bryan Dearsley
The rescued dolphins at the Dolphin Research Center in Marathon are extremely friendly (Photo by Bryan Dearsley)

Our final stop for this leg of the journey was Marathon. And here鈥檚 where we cheated a little. As timeshare owners (that鈥檚 a story for another day), we鈥檇 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鈥檛 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鈥檚 also popular with fisherfolk.

We were also treated to some spectacular sunsets in Marathon, with the resort鈥檚 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

Key West Sunset Photo by Bryan Dearsley
A spectacular sunset at White Street Pier, Key West (Photo: Bryan Dearsley)

Driving across the new Seven Mile Bridge was definitely one of the highlights of our Miami to Key West adventure. It鈥檚 even more incredible when you realize you鈥檙e over water the entirety of the way, something that鈥檚 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鈥檒l come to Bahia Honda State Park. It鈥檚 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鈥檚 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鈥檚 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鈥 鈥淢agic.鈥 And she was right. It was a truly magical moment.

The Bottom Line

GPS showing Overseas Hwy photo Bryan dearsley
Don't be surprised if your GPS shows nothing but water (Photo: Bryan Dearsley)

There鈥檚 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鈥檒l get you to all the fun and back relatively quickly. And hey, after all that driving, you鈥檒l 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鈥檚 less crowded with equally breathtaking views, but you鈥檒l need to buy a drink or two (hey, it鈥檚 Key West, remember, so that鈥檚 what you鈥檙e 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鈥檛 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鈥檙e traveling with kids as it鈥檚 generally quieter and there鈥檚 a children鈥檚 playground.

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