Key West — Hanging Out in America’s Southernmost City

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In honor of Hemingway’s famous 6-toed cats, we’ve compiled six musts for your clients to do while visiting the U.S.’s southernmost city, Key West.

6. Beyond that Famous Sunset

I get, it’s crazy to think of visiting Key West without heading to Mallory Square for the destination’s famous sunset, but once your clients have done that, then recommend they head on over to South Beach, where you can sit on the pier or beachside and watch as the day slips into night. There are less crowds, your clients can take a stroll along the beach, or maybe they’ll want to pop into the Southernmost Beach Cafe for a bite to eat. Here, they’ll also find The Southernmost House (now a hotel), circa 1897 and where five U.S. presidents have been honorary guests. Also, the the Southernmost Point in the USA buoy is right around the corner (that’s a bit busier due to the photo-op).

5. Ride a Vintage Limo Along Duval Street

The author and her family.

For clients who love the spotlight…and also learning about history, specifically about former president Harry S. Truman, recommend the VIP White Glove Tour at the Harry S. Truman Little White House, one of the destination’s most iconic museums and Florida’s only presidential museum. Zabrina, who is not only quite charming, but is also very well versed in Truman history and lore, guides visitors who opt for this tour through the Little White House, pointing out the most interesting of details, as well as through galleries filled with priceless Truman objects not on public display. Your clients will also get to hold presidential belongings…as they don white gloves, of course. The cherry on top? Riding through Key West and along famous Duval Street in a vintage presidential limo that Truman used during his 1945-53 presidency. It’s hands-down one of the coolest must-do’s in Key West.

4. A View from the Top

Right off Truman Avenue, there’s the Key West Lighthouse & Museum—climb the lighthouse’s 88 steps to the best views of the city. The complex is brimming over with trees and is also home to the Keeper’s Quarters Museum, full of great details that tell the stories of the keepers and their families. It’s a great place to wander into if your clients want to learn more about the area’s history as well as the other lighthouses that dot Florida’s East coast.

3. A Literary Giant Slept Here

Right across the street from the Lighthouse, your clients will find the Ernest Hemingway Home & Museum, where the great literary figure Ernest Hemingway lived. This is a place—even if your clients aren’t literary hounds—to stroll through at a leisurely pace. The gardens are full of hidden details—there’s even a cat graveyard and do notice the names; the home is filled with gems that recount Hemingway’s epic and fascinating life; and the study in which he wrote is a thing of beauty. Of course, don’t leave without petting those adorable cats…and do sneak into the gift shop (one doesn’t walk away empty-handed).

2. Take a Bite Out Of…

Well, your clients will want to take a bite out of everything on the menu at Half Shell Raw Bar, which also offers the prettiest views of the marina—ideal time to come by is right before the sun starts to set, so you can catch a glimpse of that as well. The food is heavenly—we highly recommend as many items from the raw bar as possible (oysters on the half shell!), topped by the delicious lobster egg rolls, with a side of the fresh catch of the day, or a fish & chips basket…the list goes on. AND tell your clients that they dare not leave the premises without trying the bread pudding (it has a special ingredient that takes it over the top). For more on the Florida Keys & Key West, visit

1. Vintage Accommodations

Our favorite part of our visit to Key West, though? The accommodations at Kimpton Key West. The Kimpton collection in Key West is actually made up of five VERY boutique properties sprinkled throughout the destination—Winslow’s Bungalows, the largest of the properties with 85 accommodations and three pools; the Lighthouse Hotel, neighboring the Key West Lighthouse and across the street from the Ernest Hemingway Home & Museum; Ella’s Cottages, overflowing with sweet charm; the elegant and historic Ridley House, harking back to 1884; Fitch Lodge, for on-the-go explorers. Your clients will find hidden gardens, pools embraced by overflowing greenery, beautifully designed living and public spaces, a décor that embraces the destination, but never borders on the gaudy, and top-notch service. This collection is made for travelers who want to be a part of the local fabric.

For more on Kimpton Key West, visit