
KEY WEST, Florida – 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. For golfers, there is the Key West Golf Club. Technically on Shock Island but within Key West city limits, Key West GC is an entertaining 6,500-yard, Rees Jones design spread over 200 acres of prime Conch Republic real estate. The course is loaded with South Florida wildlife, but it’s biggest claim to fame is the eighth hole.
Called “The Mangrove,’’ hole, it generally plays 146 yards from the tips. The greens is obstructed by a long stand of low-lying mangroves, so first-timers need to use the big flag stick to aim correctly.
The good news is that the green is fairly large, so if you can avoid the protective bunkers, par is very doable. Even for higher handicap players, the Mangrove Hole is worth playing from the tips.
Away from the course, 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).
https://www.hemingwayhome.com/
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.
http://www.papaspilar.com/#/papaspilar/landing
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.
http://rodriguezcigarskeywest.com/
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.
https://www.havanacabanakeywesthotel.com/
Want to go a bit more upscale? Casa Marina, a Waldorf Astoria Resort, might be Key West’s most desired destination.
The oceanfront resort has four restaurants and lounges, including RUMba, which of course rum-crafted cocktails, spa and beachside rental services for activities such as snorkeling, kayaking and wave runners.