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Personal Finance > Smart Spending > Travel
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Island-hopping in the Keys
The 100-mile drive across the Florida Keys is a classic winter road trip.
November 27, 2002: 2:18 PM EST
Paul Lukas, Money Magazine Contributing Writer

KEY LARGO, Fla. (Money Magazine) "You're going to Key West? That doesn't seem like your kind of place." That's what most of my friends said when I told them my travel plans. The funny thing is, I never said I was going to Key West.

What I'd said was, "I'm going to the Florida Keys." But as I discovered, for many people the Keys pretty much begin and end with Key West. Even my editor kept referring to this article as "the Key West story."

All of which is a shame because Key West, despite its historical charms, has become a tourist nightmare, lousy with T-shirt shops and Margaritaville kitsch. It really isn't my kind of place.

But I was interested in the rest of the Keys, a series of tiny islands extending over 100 miles from the Florida mainland (the name Keys comes from the Spanish word cayos, which means small islands). Originally settled by Bahamians, the Keys are a unique corner of America (and of Florida, for that matter): an extended stretch of island culture replete with picture-perfect beaches, tropical birds and other exotic wildlife, countless seafood joints and marine activities like fishing, kayaking, snorkeling and scuba diving.

There's also that elusive but palpable "anything goes" sensibility so unique to island living, which historically has made the Florida Keys a refuge for artists, homosexuals, outcasts and eccentrics.

Many people bypass all of this and fly into Key West, but I saw the Keys as a great road trip waiting to happen. The islands are connected by the southernmost stretch of U.S. 1, known as the Overseas Highway, a massive causeway that's a story in itself.

Originally built for the Florida and East Coast Railroad in 1912, it was designed to provide a rail link between southern Florida's resorts and Cuba (a short ferry ride from Key West). But the tracks were destroyed by a 1935 hurricane and later converted into a highway. With the Atlantic Ocean on one side and the Gulf of Mexico on the other, views from the roadway are spectacular.

There's also a handy mile-marker address system (Florida City, at the highway's eastern end, is MM 127; from there the miles count down to MM 0 in Key West), which makes it easy to locate businesses along the highway's entire length.

The Keys are stiflingly hot in the summer, overrun by marauding college students during spring break and vulnerable to hurricanes in the fall, so the best time to go is in winter, when the weather is pleasantly warm. With that in mind, my pal Laura and I headed south last February. Our plan was to fly to Miami and take six days to drive from there to Key West, where we'd head straight to the airport and fly home. Here's how it went.

Day one

We arrive in Miami, rent a car and head south, stopping along the way at two small but endearing tourist attractions. The first is the Gold Coast Railroad Museum (www.goldcoast-railroad.org). Its collection of historic trains and memorabilia is highlighted by the Ferdinand Magellan, a gorgeous 1942 Pullman railcar that was built for Franklin Roosevelt and later used by Presidents Truman and Eisenhower. There are also locomotives from the old Florida and East Coast Railroad, which plied the tracks of the Overseas Highway before the 1935 hurricane.

Next stop, a bit farther south, is the classic old tourist trap, Coral Castle (Homestead, Fla.; www.coralcastle.com), a bizarre sculpture garden of massive coral carvings made in the 1920s and '30s by one Ed Leedskalnin, a Latvian immigrant who created the place during a 20-year fit of depression after being jilted by his true love.

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The story sounds at least mildly apocryphal, but Leedskalnin's sculptures have that eccentric air of accidental genius found in the best folk art, providing us with a perfect sense of vacation escapism as we move on and arrive in Key Largo, the first and largest of the Keys.

Day two

We begin our first full day in the Keys at John Pennekamp Coral Reef State Park (MM 102.5, Key Largo; www.pennekamppark.com or www.floridastateparks.org), where we hope to go snorkeling. But tours have been canceled because of poor visibility, so instead we check out the park's small but lovely aquarium and then rent a kayak and spend a few hours tooling around a series of channels lined with beautiful mangrove trees.

John Pennekamp Coral Reef State Park (Photo: Florida State Parks)  
John Pennekamp Coral Reef State Park (Photo: Florida State Parks)

The mangroves, with their huge, intertwining root systems, are everywhere down here, and we see more of them later on at the Florida Keys Wild Bird Center (MM 93.6, Tavernier; www.wildweb.org/wbc), whose marshy grounds are alive with countless pelicans, egrets, ibises, herons and cormorants. It's an amazing place, and the birds are astonishingly tame. One pelican even "adopts" us, following a few steps behind as we walk the facility's boardwalked nature trails.

Day three

A very active day, beginning with a visit to Robbie's Marina (MM 77.5, Islamorada; www.robbies.com), where we are able to rent another kayak and paddle about a mile into the ocean to Indian Key, an uninhabited 10-acre island that was once a pirate haven and then the seat of Dade County, until an Indian attack in 1840 destroyed almost everything there.

We land on a small beach, hike through some mangroves and take a self-guided tour of what's left of the old settlement: cisterns, the ruins of a few buildings, a watchtower and a grave, all of it explained by signage maintained by the Florida State Park System -- an excellent place.

After paddling back to Robbie's, we go next door to Sea-n-Swim Tours (MM 77.5; www.seanswim.com) and sign up for an afternoon snorkeling session in the Gulf. Proprietor Sean Starling is extremely helpful and enthusiastic, and by day's end we've seen umpteen fish, several lobsters and lots of gorgeous coral. As a first-time snorkeler, I'm blown away by the colors, the clarity and the proximity to the fish -- it's like being on the other side of the glass at an aquarium.

Day four

As you might expect, Sea World-ish marine attractions abound down here, and today we visit one of the most interesting ones: the Dolphin Research Center (MM 59, Grassy Key; www.dolphins.org), a non-profit facility that's home to about a dozen dolphins and sea lions, many of them retired or donated from commercial aqua parks. We watch the dolphins do their tricks, hypnotized by their supreme cuteness, and then tear ourselves away.

Pigeon Key  
A house on Pigeon Key (Photo: Pigeon Key)

Next we drive to the foot of the Seven Mile Bridge -- the longest bridge in the Keys and among the longest in the world -- and take a tour of Pigeon Key (MM 47; www.pigeonkey.org), a five-acre island that once housed the railroad workers who built the bridge back in the early 1900s. It's now been turned into a museum park, with most of its original buildings intact and assorted exhibits about what life was like for the families who worked there -- a rare glimpse into the Keys' early developmental days.

Day five

Despite being surrounded on both sides by water, we've somehow managed to get this far without stopping at the beach, a situation we remedy by beginning the day at Bahia Honda State Park (MM 37, Big Pine Key; www.bahiahondapark.com), whose white-sand beaches are renowned as the most beautiful in the Keys. It lives up to its reputation, and we spend a few hours reading the Sunday paper and generally lazing about on the gorgeous white sand.

But there's lots more to do, so we move on to the National Key Deer Refuge (Key Deer Blvd., Big Pine Key; 305-872-0774; nationalkeydeer.fws.gov), home to the endangered Key deer, a diminutive species typically measuring two to three feet high. Numbering just 800 -- up from an alarming 27 in 1957 -- they're found only on Big Pine and No Name Keys, and we spend a good chunk of the afternoon fruitlessly tramping around nature trails in search of them.

Finally, near dusk, there they are -- first a pair of deer, then a group of about 15, happily munching on the local vegetation, even cuter than the dolphins. We watch until daylight fades away and then quietly leave them be.

Day six

One reason it's best to visit the Keys in winter is that mosquitoes are a problem the rest of the year -- such a big problem, in fact, that in 1929 a fellow named Richter Perky built a 35-foot tower to attract bats, which he figured would eat the skeeters.

The insect-control plan was a bust, but the Perky Bat Tower remains (MM 17, Sugar Loaf Key). The louvered pine tower, now a National Historic Landmark, sits alone and batless, silently mocking its creator. But give Perky his due: His pine tower has survived countless hurricanes in its 70-plus years.

From there it's a short sprint to the town of Key West, where we can't resist the lure of having our photos taken next to the Southernmost Point in the Continental United States, just like all the other tourists. We also check out the local cemetery, which, much like those in New Orleans, features lots of spooky-looking aboveground crypts because the area's high water tables make underground burial impractical.

As for Key West's other dubious charms, they'll have to wait for another day, as it's time for our flight home.

Paul Lukas liked snorkeling so much that he's now setting his sights on scuba.  Top of page




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Most stock quote data provided by BATS. Market indices are shown in real time, except for the DJIA, which is delayed by two minutes. All times are ET. Disclaimer. Morningstar: © 2018 Morningstar, Inc. All Rights Reserved. Factset: FactSet Research Systems Inc. 2018. All rights reserved. Chicago Mercantile Association: Certain market data is the property of Chicago Mercantile Exchange Inc. and its licensors. All rights reserved. Dow Jones: The Dow Jones branded indices are proprietary to and are calculated, distributed and marketed by DJI Opco, a subsidiary of S&P Dow Jones Indices LLC and have been licensed for use to S&P Opco, LLC and CNN. Standard & Poor's and S&P are registered trademarks of Standard & Poor's Financial Services LLC and Dow Jones is a registered trademark of Dow Jones Trademark Holdings LLC. All content of the Dow Jones branded indices © S&P Dow Jones Indices LLC 2018 and/or its affiliates.