The 2 ways to see the Florida Keys

Florida Keys
Dusk at the Tranquility Bay Beachfront Hotel & Resort in Marathon, Florida. |

There is more to the Florida Keys than just Key West.

In fact, the archipelago spans about 125 miles and consists of 1,700 islands. Connecting some of the islands are the 42 bridges that carry the Overseas Highway, as U.S. Route 1 is called in these parts, to its terminus at mile marker zero by the stately courthouse in Key West’s historic downtown.

I discovered the best places to go during a recent trip, when I split my time between sleepy Marathon and action-packed Key West.


About two hours south of the Miami airport is Marathon.

Technically incorporated as a city, this is for all intents and purposes a small town of strip malls, condos, marinas, fish shacks serving up the freshest of fresh seafood, and vacation rentals targeting snowbirds. It’s also a great base for anglers booking fishing charters.

I stayed at Tranquility Bay Beachfront Hotel & Resort, which combines the comfort of home — some units have a full kitchen — with the amenities of a hotel, including three pools and a private beach on the Gulf of Mexico. Guests taking advantage of work-from-home flexibility will find this a very relaxing place to telecommute.

The hotel’s Butterfly Café has an elegant dining room that reminded me of a great room in an old island plantation home. It was a very enjoyable dining experience. Alternatively, drive about 45 minutes to Islamorada for a cold beer at the aptly named Islamorada Beer Company followed by dinner at Chef Michael’s.

Local attractions include the Turtle Hospital, which provides care for various species of sea turtles. Be sure to also take one of the tours to Pigeon Key. This is where workers lived when a railroad — the Overseas Highway’s predecessor — was built by Gilded Age industrialist Henry Flagler.

Key West

Key West’s wild-and-crazy reputation is somewhat unfair. While that kind of experience is readily available there is much more on offer than debauchery.

In fact, it’s impossible to visit and not be taken in by the immense charm, great history and vibrant culture. No wonder artists and writers, including Ernest Hemingway and Tennessee Williams, have lived here. This makes it as family-friendly as any other destination.

I ignored most of Duval Street, the main street lined by tacky souvenir shops and endless establishments of varying repute. Instead, I explored side streets with quaint old buildings, including Hemingway’s one-time house (now a museum). Many of the houses feature details associated with conch architecture, a vernacular style popular with immigrant shipbuilders and carpenters from the Bahamas in the late 1800s.

Other must-visits in Key West are the original Lighthouse and Keeper’s Quarters, President Harry Truman’s Little White House, the former federal building-turned-Art & History Museum and the Mel Fisher Maritime Museum, the latter of which includes artifacts recovered from shipwrecked Spanish galleons and fascinating exhibits on the rafts that brought Cuban refugees to the shores of Florida.

Consider staying at one of Kimpton’s five hotels. Each property is located downtown and housed within beautifully converted structures, including period conch homes. For dinner try Matt’s Stock Island Kitchen & Bar inside the fashionable Perry Hotel, which is located right across the Cow Key Channel from Key West. It also has one of the best key lime pies anywhere in the Florida Keys.

If you go

Fly into Miami or Fort Lauderdale and out of Key West, which is served by all of the big airlines and car rental agencies.

Spires and Crosses is a weekly travel column. Follow @dennislennox on Twitter and Instagram.

Dennis Lennox writes about travel, politics and religious affairs. He has been published in the Financial Times, Independent, The Detroit News, Toronto Sun and other publications. Follow @dennislennox on Twitter.

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