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Cruise Diva Goes Ashore in the Caribbean
Sights to see & things to do

Key West, Florida

Yes, it is a Florida city—America’s southernmost city, in fact—but it has the look and playful feel of its Caribbean neighbors. The end of the line in the Florida Keys, Key West is becoming one of the favorite port stops on western Caribbean itineraries and for good reason, it’s historic and has plentiful sights and attractions to pack into a half day visit. 

Cruise ships dock alongside the piers adjacent to Mallory Square, the main plaza, or at Outer Mall, from where they are shuttled via Conch Train to Duval and Front streets. Everything is close by—Key West is only 2 miles wide and 4 miles long.


Getting around couldn’t be easier on the Conch Tour Train or Old Town Trolley. Ship’s excursions are a waste of money here. Catch the Conch Tour Train in Mallory Square for a 90-minute narrated tour up and down Key West’s most interesting streets. It’s a great way to learn about the area and its famous residents, but it doesn’t stop. The Old Town Trolley is more flexible, allowing riders to get off and explore on their own and then catch another trolley later. Watch for the signs near the pier or throughout town to board the trolley and hop off to see these sights...

  • Audubon House is a rather misleading name for this house on Greene Street. While the famous naturalist John James Audubon didn’t live here, it’s full of his engravings and the lush tropical gardens are a must-see. 

  • The former vacation home of Harry S. Truman (the Little White House) is a small house that takes less than an hour to see; however, the lines can be lengthy for admission. 

  • Long lines are also sometimes a problem at the Hemingway House, but it’s worth the wait to tour Ernest Hemingway’s home and the studio where he wrote some of his most famous works. Descendants of his polydactl, or six-toed, cats still live on the grounds. 

  • The Mel Fisher Maritime Heritage Society Museum displays an extraordinary collection of salvaged Spanish doubloons and gold and silver bullion. Treasure hunting diver Mel Fisher and his associates brought up over $400 million worth of gold and silver from shipwrecked Spanish galleons.

For an offbeat experience, stroll through the Key West Cemetery where you’ll see headstones with inscriptions such as, “I told you I was sick” and “At least I know where he is sleeping tonight.” 

The most compelling activity in Key West is sunset watching when the locals flock to Mallory Dock for a nightly celebration. Unfortunately, most ships are required to leave before this surreal entertainment.


Locals view cruise ship shoppers with a jaundiced eye and sell some of the most outrageously tacky merchandise you’ll ever see. Worth a stop is Key West Aloe for men and women’s toiletries based on, what else—aloe. Numerous galleries are well stocked with prints and watercolors by local artists. Cigar aficionados will appreciate hand rolled cigars made of leaves grown from Cuban seed—available at a number of cigar shops scattered throughout town.

The shop in the Mel Fisher Maritime Heritage Society Museum is the source for Spanish doubloon pendants and jewelry.

Don't pass up a frozen Key Lime Pie on a stick.


Beaches are almost an afterthought in Key West. Most are manmade and not memorable. The closest to the cruise ship docks is Fort Zachary Taylor State Beach, accessible through the gates leading into the Truman Annex. 

Instead of the beach, head for another kind of watering hole. Some of the funkiest are Sloppy Joe’s, Captain Tony’s Saloon, Hog’s Breath Saloon, Jimmy Buffet’s Margaritaville, and Schooner Wharf. Even if you don’t drink, you can boast you “got wasted away…” in Key West.

Fodor's Caribbean Ports of Call 2013
is all you need to plan your days ashore, PLUS a cruise primer section and cruise line profiles by Cruise Diva, Linda Coffman

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