Hemingway and beyond at Key West

Let’s set the record straight about Key West. Despite its reputation, the Conch Republic is more than  Duval Street, Mallory Square, Captain Tony’s Saloon and Sloppy Joe’s Bar. Sure, each has contributed to Key West’s fame (and infamy), but the Southernmost island in the U.S. has a lot of history and culture to share.

In Key West, understand, there’s always something to talk about and some place to explore. The best way to begin exploring Key West is ride on the Conch Train. It’s a 90-minute tour of the island that takes guests to more than 130 sites, including the President Harry Truman’s Southern White House, the marker at the Southernmost point in the U.S. (only 90 miles from Cuba) and Ernest Hemingway’s house. The Spanish Colonial-style house is kept as it was when Papa and his wife, Pilar, lived in it in the 1930s. Tours are available of the home and grounds (complete with the famed six-toed cats).


A pilgrimage to the Hemingway House – the first on the island with indoor plumbing – is one of the “must do’’ things in Key West. And don’t worry about missing your ride. The Conch Train makes a few stops along its journey, so passengers can get off to explore and then re-board another train. There is a not better to get familiar with Key West, particularly for first-timers who want to see more than just the usual spots. Locals and frequent visitors, too, each enjoy the occasional ride to the Conch Train to refresh themselves with the island.

Hemingway’s likeness and spirit each are all over Key West. The legendary author first visited there in 1928 and owned the house until his death in 1961.

Did somebody say “spirit?’’ Located in an old brick building only a few blocks off Duval Street, Papa’s Pilar Rum Distillery – Hemingway Rum Company – offers daily guided tours of the rum-making process and yes, even a few samples of its Pilar Blonde and Dark rums after each tour. My choice? Go with the Dark, or better yet, mix the Blonde and Dark for a smooth taste. Papa would be proud.

Papa’s Pilar Rum


What’s a good rum without a good cigar? Rodriguez Cigar Factory, has been making handrolled cigars in Key West for more than 30 years. Its Series 84 cigars are regarded as among the finest in the world. The company has a terrific humidor room and co-owner Danny Difabio, whose grandfather immigrated from Cuba, might even roll you a stogie. Located just a few blocks from Mallory Square, Rodriguez Cigar Factory is another “must visit’’ destination in Key West. For an added treat, ask to see the company’s upstairs storage room where it cures cigars for up to a one year.


Danny Difabio

For those who don’t want to fight the Mallory Square  crowds for the “Cat Man’’ show and a legendary Key West sunset, hop the ferry for a 10-minute to Sunset Key for dinner at Lattitudes. Make sure to get an outside table for the best sunset view while enjoying the restaurant’s outstanding steak and seafood menu.

The cottages are outstanding – but uber expensive – accommodations, great for honeymoons and anniversaries. Back on Key West, there is no shortage of resorts and hotels of all kinds and prices.

Among my favorites is Havana Cabana, a mid-priced boutique hotel located on Roosevelt Blvd., near Old Town. The 106-room hotel celebrates Key West’s Cuban heritage, as well as providing colorful island vibe. A 15-minute free shuttle to Mallory Square, Havana Cabana  is a great headquarters for everything Key West. There’s plenty to do on-site, too, from splashing in the island’s largest fresh water pool, to grabbing a Cuban sandwich – perhaps the best in Key West – at Floridita food truck near the pool and bar area. The Mojitos Pool Bar, open after hours, serves 25 versions of Cuba’s legendary rum cocktail.

Havana Cabana

Havana Cabana also has scooters to rent – a fun way to explore Key West – and a concierge who can set up anything from dinners to deep sea fishing.  Previously known as The Inn at Key West, the hotel opened this past April after a complete renovation following Hurricane Irma this past fall, including the Cuba-themed art work in the lobby and in each guest room. Each guestroom has a pool or gulf view with a lanai or balcony.


“There is a lot of history between Key West and Cuba,’’ said Havana Cabana General Manager Mark Vose. “There are a lot of Key West families that still have relatives in Cuba, so we wanted to tie that in. Nowhere else on Key West will you find a hotel that tries to bring those two cultures together.

“We’ve definitely seen an uptick in the popularity of the hotel. Our repeat customers – we have a lot of them – are ecstatic about the property and the locals are talking a lot about it.’’

And in Key West, there always is something to talk about.


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