Key Largo to Key West: An Historic Route & Modern-Day Haven

Sailing alongside Florida’s Overseas Highway, the road that follows the route of Flagler’s historic East Florida Railway from Miami to Key West, it’s easy to picture the turn-of-the-century developer pushing to expand his vision of Florida.

I wonder if Henry Flagler ever went sailing. Sailing alongside Florida’s Overseas Highway, the road that follows the route of Flagler’s historic East Florida Railway from Miami to Key West, it’s easy to picture the turn-of-the-century developer pushing to expand his vision of Florida. After developing Palm Beach and Miami as major cities, Flagler set out to connect them to Key West via railway, which would open up trade with Cuba and points west following the completion of the Panama Canal.

Flagler looked at sand-strewn, uninhabited Florida and saw an opportunity for development made possible through transportation. He completed his East Coast Railway in 1912, in the process throwing open what would become a great American vacation destination, complete with sportfishing, spring-breaking and, of course, sailing.

I thought about Flagler as we sat contentedly at anchor off the beach at Bahia Honda National Park. We were sailing Keremeos, a 44ft Fountaine Pajot Orana from 360 Yachting, and were halfway through our one-way charter from Key Largo to Key West. Here in the Bahia Honda anchorage, two elevated highways stretched into the distance on either side of our catamaran. To the north, the modern-day Route 1 was aglow with passing taillights. To the south were the remains of Flagler’s original East Coast Railway, which was destroyed in the Labor Day Hurricane of 1935. In the depths of the Depression, the railway didn’t have the funds to rebuild, so it was sold to the State of Florida. Today, broken segments of the elevated road are sometimes used in Hollywood chase scenes that involvecars flying off unexpected precipices.

Conveniently, one such broken segment also serves as a great entrance to this quiet Florida Keys anchorage.

A Florida Keys charter is best done as a one-way trip, as the prevailing winds blow from the east-southeast and you sail south and west. The Keys run parallel to a barrier reef (the only one in the United States), with three- to four-mile-wide Hawk’s Channel separating the two. Following this geography, the ideal Keys charter itinerary is to zig and zag between key and reef, from anchorage to snorkelage.

Our crew of six began its journey in Key Largo on the nearly new, stunning Keremeos. Navigating around “Crash Corner” in a crowded Key Largo marina was the most nerve-wracking part of the entire trip. After that, we were free and easy, sailing in Hawk’s Channel. Sailing just a few miles south we made our first stop near the Key Largo Marine Sanctuary, where we picked up a mooring ball and spent several fruitless minutes looking for the famous Statue of Christ of the Abyss, a bronze duplicate of a seafloor statue located off the coast of Genoa, Italy. Despite our best attempts, the 9-foot statue eluded us, so we left that and continued on to the next underwater spectacle at Molasses Key.

Here, we discovered an impressive natural aquarium, where parrotfish and barracuda provided a lively show as well as a taste of things to come.

After that, we tucked away for the evening in the lee of Tavernier Key. Though this was our only night spent far from civilization, the Keys offer plenty of quiet, isolated mangrove coves like this one, where the stargazing is only outdone by the wildlife sightings.

As I like to do on charter, I had booked in advance a half-day commercial fishing trip for my crew out of Holiday Isle on Islamorada, which is where we headed the next morning. Though I love to cook and eat locally caught fish, I’m a reasonably lousy fisherwoman, and I’d much rather leave the hooking and the casting to the pros.

An extensive online search brought me to Capt. Robert and his first mate, Casper, aboard the 1964 sportfishing boat Restless Too. After tying Keremeos alongside the seawall at Holiday Isle Marina on the east side of Whale Channel on Islamorada, we walked the short distance to the opposite side of the channel, where dozens of sportfish boats sat at the ready, prepared to take tourists out for a spin.

Capt. Robert was the real deal, a pro fisherman with years of Keys fishing experience, an epic classic rock playlist and an entertaining 10-year-old son/cabin boy who monkeyed around the boat like he’d been born on it—which he very well might have been. Four miles offshore, the day started out slowly, as Casper tossed blocks of frozen chum and bonita overboard to whet the fish’s appetites. He then set two lines and a sailfish line, and we waited. Sure enough, the surrounding boats dispersed, and we were soon catching more fish than we could eat: 15 yellowtail, a pair of mackerel and a 15-pound grouper (which we had to throw back, as it wasn’t in season). We came close to catching an 8-pound yellowtail, but were bested by a barracuda that chomped the thing in half before we could boat it.

Robert and Casper were quick, professional and very entertaining. Back at Whale Harbor, they cleaned and filleted everything for us while we enjoyed tuna sliders in the nearby bar. That night, my friend and crewmate Matt grilled up a divine dinner of pan-seared yellowtail accompanied by asparagus. Not only was the fish delicious, but Matt assured us there was enough for at least two more meals.

Once we were sure we’d taken advantage of all Holiday Isle Marina had to offer—the bars, the shorepower, the facilities and the convenience store—we sailed on. As Capt. Robert pointed out the day before, low tide at Whale Channel is a popular spot for powerboaters to raft up and chill out on the exposed sandbar. A powerboat beach party translates to sailboat badness, so we timed our departure with high tide and headed toward Alligator Reef for more exceptional snorkeling.

After that, we headed for the well-known Boot Key Marina on Marathon Key. But there wasn’t much breeze and the going was slow, so we motored most of the way and managed to nab the last mooring ball from the friendly dockmaster. I’d read horror stories about this marina being plagued with dirty water and derelict vessels, but was pleased to discover Florida has done a nice job cleaning it up. Traffic to and from the marina is heavy in the afternoon, but at night, it’s nice and quiet, and the sunset views are terrific.

As promised, Matt cooked up a second batch of our catch—the two mackerel, which he grilled and served with green beans. Of course, fresh-caught fish is never as fresh the second night, but it was still a treat.

The next day’s sail followed our pattern of snorkelage/anchorage, but this snorkel spot, Sombrero Key, was my personal favorite. The area is marked by a picturesque red lighthouse that serves as a navigational beacon when making your way there. Upon arrival, we found a dozen mooring balls east of the lighthouse. From the stern of Keremeos, we swam along them toward the lighthouse and were thrilled by the sight of massive parrotfish, colorful coral and plentiful barracuda stretching back their lips to expose their vicious-looking chompers.

After a quick lunch on board, we sailed off to Bahia Honda, sailing alongside the Seven Mile Bridge, the longest of Route 1’s 43 bridges. Lying in the triangle between Route 1, Flagler’s abandoned railroad bridge and the beach, the anchorage at Bahia Honda is a strange place, where seaside tranquility meets bustling civilization. The beach was the nicest we saw, and a three-mile running path ashore was a welcome escape, but the anchorage wasn’t what you’d call “remote.” My mother and crewmate, who is an outspoken seeker of peace when traveling outdoors, wasn’t fond of the noise and glow from the traffic, and while I appreciated the contrast between nature and civilization, I could see her point. We sat on the beach together, debating the matter and watching the sunset, until we transitioned to debating whether the fin in the swimming area belonged to a dolphin or a shark. We never did decide.

One unavoidable aspect of a one-way charter is that you spend a lot of time thinking about and planning for the Final Destination, in our case Key West. None of us had been to this fabled sailors’ haven, and I’m happy to report, it did not disappoint.

Though we’d hoped to find a slip within walking distance of the action, the only spot available for our big cat was the Garrison Bight Mooring Field north of town. This required a dinghy ride followed by a taxi ride whenever we wanted to get to town, but we made do and spent two days touring around the fabulously eccentric Key. 

We did the tourist things—visited the southernmost point in the United States, climbed the old Key West Lighthouse, laughed at the six-toed cats in Ernest Hemingway’s home—and we enjoyed our fair share of excellent local food and music. We burned our tongues with hot sauce at Peppers of Key West, and cooled down with oysters at the Schooner Wharf Bar. We watched sword-swallowers, fire jugglers and tightrope-walking cats perform in Mallory Square. We saw six live music acts in one night, ranging from dueling pianos to a band of intensely muscular leather-clad men playing rock ballads to a lone guitarist singing about “Who needs condoms when you’ve got luck?” It was an exciting way to conclude our tour of the Keys, and, of course, it came with a world-class Key West sunset. 

My crewmate Jess had a long-standing life goal to drive a convertible along Route 1, and we’d found our perfect excuse. First thing Saturday morning, Capt. Joe of 360 Yachting arrived to take Keremeos off our hands, and we were free to go, completing a reverse and sped-up version of our previous week’s sail. We passed the anchorage at Bahia Honda, drove over the Seven-Mile Bridge, waved to Capt. Robert in Islamorada, and drove over islets and mangroves all connected by this storied highway.

Again, I thought about its roots and the man who’d built it. Over the course of 30 years, Flagler invested some $50 million into developing Florida. Near the railway’s completion in 1912, Flagler said, “I believe this state is the easiest place for many men to gain a living…I do hope to live long enough to prove I am a good business man by getting a dividend on my investment.” In 1913, at the age of 83, Henry Flagler passed away. I’m glad he introduced America to Southern Florida, and I sure hope he got to enjoy it from the helm of a sailboat.



At The Helm: Man Overboard!

Imagine this simple scenario: the boat’s powered up, sailing close-hauled in a building breeze under full sail. I come on deck as the skipper during the watch change to make sure the new crew is comfortable and the boat is properly set up for both the current conditions and more


Contrasting X-Yachts & Moody Cruisers

One of the most fascinating things about sailboats is the different ways that sailors, naval architects and builders will approach a single design problem. The result has been a bewildering array of rigs and hull forms over the years, and in the case of the two boats we’ll be more


Cruising Charter to Croatia

As is the case with so much of the Mediterranean, to sail in Croatia is to take a journey through time. Centuries before the birth of Christ, Greeks traded amphoras of oil, wine and grain across these waters. During the first millennium, the Romans built lavish palaces and more


Alicante Announced as an Ocean Race Europe Stop

The Ocean Race Europe, a new event in offshore sailing, will include Alicante as one of four stopover cities. This European offshoot of the former Volvo Ocean Race will include the biggest change to the racing rules under the new title—fully crewed IMOCA 60s will join the more


Preparing for a Doublehanded Race

A few months ago we took a look at the development and attraction of doublehanded racing (Two to Tango, June/July 2020). Hopefully, that served to whet your appetite. If so, the question becomes: “How do I get started? The good news, as we explained in Part 1, is that if you are more


A Key Approach to Passagemaking

How you approach offshore sailing is key to the success of each passage. In addition, some of the most valuable, even crucial attitudes and skills may not be either learned or valued in everyday life on shore and may even fly in the face of talents that are greatly admired and more


Point of SAIL: Mary Crowley of the Ocean Voyages Institute

In this episode of Point of SAIL, Principal Editor Adam Cort talks with Mary Crowley, founder and executive director of the Ocean Voyages Institute, a not-for-profit based in California that has been both educating sailors and working to preserve the health of the world’s ocean more


Tracking and Catching Plastic Waste

Plastic waste—in the form of everything from plastic soda bottles to abandoned fishing nets—constitutes a major threat to the health of the world’s oceans. Giving the immense size of an ocean, though, actually finding all the plastic floating around out there in a time-efficient more