Posted by: Jerry Garrett | December 9, 2009

My 36 Hours in Key West, Florida (Full Moon Optional)

Home of the Sunset: Mallory Square in Key West, Florida (Jerry Garrett Photos)

What is the best way to get to Key West, the crown jewel of the string of gems that are the Florida Keys?

Expensive commuter flights, cruise ships and even a ferry from Fort Myers are possibilities, but most often, I drive. It takes a good three hours from Miami, with plenty of speed traps along the way, ruthlessly enforcing the 45-55 m.p.h. limits. But the Florida Keys reveal themselves slowly, tantalizingly, via the historic, 127-mile-long Overseas Highway; the waters of Florida Bay become more tropical, more turquoise with each mile. Also, the earlier in the day you drive there, with the morning sun still behind you, the prettier the waters. But it is also fun to race the sunset, with the sea ahead sparkling like diamonds.

The objective is to reach Key West before sunset, because that is one of the main pleasures of being there.

Shadows lengthen; crowds grow at Mallory Square

Crowds gather – along with a growing freak show of carnival-type entertainers – each night, weather permitting, in Mallory Square for the sunset ritual; bells ringing as El Sol disappears into the Caribbean, as the horizon turns orange, then crimson, then magenta.

Dinner is next up. The two best restaurants in Key West – arguably, for sure – are both named Pepe. Since you are in the vicinity of Mallory Square, why not stay there and try nearby El Meson de Pepe? This historic-looking restaurant (it’s a modern re-creation of an old government building once on the site), serves fabulous Cuban fare (like Bistec Palomilla Empanizada) and seafood at non-bankrupting prices. The mojitos? Sublime.

Seafood, Cuban, Mojitos

If you’re not too tipsy after a couple of mojitos or margaritas (or, better still, if you are), wander down Duval Street, Key West’s main drag, to soak up the atmosphere and the party vibe. Somewhere, at any given time, you are guaranteed to hear someone singing “Wasting Away in Margaritaville”.

Do the Duval Crawl

If you’ve booked at room at, say, the Orchid Key Lodge (formerly the Key Lodge) or one of the other top-rated B&Bs at the far end of the street, you’ll end up your Duval Crawl in the right neighborhood. B&Bs are good bet in Key West, because if you choose wisely (TripAdvisor rates 103 of them), you’ll get a comforting infusion of island living, as well as the local lifestyle. Many of them are in former mansions, in a shabby chic Cape Cod style.

The B&Bs can satisfy continental-type breakfast needs (bad coffee, stale pastries, and watery O.J.), but big eaters may want to find Blue Heaven.

Conch Eagle

The alfresco dining area is under the sheltering branches of several huge trees, with a floor of dirt, beauty bark and chicken poop.(Chickens roam everywhere, with impunity in Key West; they are the national bird of the Conch Republic).  Very good food. Very strong atmosphere. Very long waits for a table (late mornings and weekends).

A bicycle rental is about $12 a day (many locations, all over town). Bikes are a good way to circumnavigate the 7-mile-long island. An increasing number of electric scooters and carts are also for rent, for the environmentally conscious motorist.

The sandy beaches along Roosevelt Blvd. are Key West's best.

The inviting waters of the gulf can be explored at the island’s only (public) sandy beach adjacent to Roosevelt Blvd. (A good overview of Key West’s beaches is found here.) Old town – the prime tourist area – is on the northwest end. Essentials like supermarket groceries, competitively priced beer, wine and spirits, clothing and household goods are sold mostly in northeast end of Key West. Key West has a rich arts community; and eclectic exhibits, galleries and workshops are scattered around town in the most unexpected places, just waiting to be discovered by the intrepid explorer.

Lunch is best grabbed on the run. If you aren’t sick of Cuban food yet, try something simple like Sandy’s Café on White Street – the best food you’ll ever have in a laundromat.

Home of good eats, clean clothes

An alternative sunset photo op is at the end of Whitehead and South streets, where a ten-foot-high concrete harbor buoy replica is located; it is painted with “Southernmost Point in the Continental U.S.A.” (it’s not, exactly, but who cares?) And some other slogans like “Home of the Sunset” (debatable) and “90 Miles to Cuba” (which is true). Other touristy things to do include touring Ernest Hemingway’s old mansion, President Harry Truman’s old hangout here, and various harbor cruises ($39 for a sunset cruise). Want more ideas? Buy a guidebook, or go online.

Dinner should be taken at the other Pepe’s. It’s a tiny place on Caroline Street, and reputed to be the city’s “eldest” restaurant. How old? In 2009, it celebrated its centennial (you do the math). Specialties include steak, steak and steak smothered in pork chops. Seriously.

The rise of the full moon, if you have timed your visit to coincide with this lunar phenomenon, is best seen along south beach. No moon? Enjoy the Milky Way.

Ground Zero in Key West

Maximum effort should be expended tonight, soaking up Key West’s oddball nightlife. The tequila-and-lime specialty of the original Jimmy Buffett’s Margaritaville, live music and insane people-watching at Sloppy Joe’s Bar, alternative lifestyle stage productions at La-Ti-Dah or several similar nightspots on Duval,  or any of the many places in town that claim Hemingway drank, fought, slept, shot, angled or wenched there.

Sleep it all off the next day; most B&Bs recognize the damage a night in Old Town can inflict – and they schedule breakfast at appropriately humane, late morning hours. The drive back out of the Keys will seem longer, going away from Cayo Hueso – its original name (from the Spanish, who originally settled it). But the long, slow drive will give you one last look at this aquamarine paradise, and make you understand why many who come here never leave.

Seven Mile Bridge, Overseas Highway, Lower Keys: You are now leaving Paradise

Jerry Garrett

December 8, 2009


  1. This blog is glorious.

    Better than guide books, you capture what makes Key West so intriguing, delicious, and impossible to forget when we’ve traveled far away from it. You capture what lives within us.

    For those who haven’t visited Key West, I hope you will soon to see why it is so memorable.

  2. […] This post was mentioned on Twitter by Steven Nicolle and Jerry Garrett, Derek Dowell. Derek Dowell said: My 36 Hours in Key West, Florida (Full Moon Optional) « Garrett On … […]

  3. Fantastic Blog! I’m with you on the drive up and down the Overseas Highway. There’s nothing like the feeling of freedom as the narrow little highway bursts forth from the trees into the wide open ocean.

    And as someone who’s been here, you know you’ve already been away too long! You’ll have to come back and share some more travel blog goodness.

    • Thanks, Michelle. There are a lot of beautiful places on Earth, but the thing that adds to Key West’s already megawatt appeal and makes it compellingly different is the people! They love the place, and want to share it with you, and make sure you have as much fun there as they do. Once the Key West bug bites you, there’s no cure!

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