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Key West is one of my favorite cruise ports. On our most recent cruise, we spent our first port day Following Hemingway’s Footsteps in Key West.
When I think of Ernest Hemingway many things come to mind. Yes, he is a celebrated writer and a fixture in American Classic Literature. His descriptive, short-sentenced writing became a style all unto his own. It is also something many other authors strive to imitate. His passion to tell a story can be felt within his written words. He wanted it to be real, authentic and that is something I most certainly can respect. However, when I think of Hemingway it is often the story of his own life that I find most captivating.

Ernest Hemingway lived a fascinating life full of adventure. He traveled the world and lived in incredible places like Paris and Havana. However, his time in Key West was where he spent the Depression years and wrote some of his most famous works including A Farewell to Arms and To Have and Have Not.

Our first port of call on our cruise last month was Key West. I always enjoy spending time in Key West and since I’ve strolled along Duval Street and seen the Southernmost Point I decided to mix things up for this visit and created a short itinerary Following Hemingway’s Footsteps in Key West.
One of the things that I love the most about Key West on a cruising itinerary is that it is such an easy and accessible port. You can just step off the ship and quickly reach many of the local sites by foot. My parents joined my husband and me as we embarked on the .6-mile trek to our first stop, The Ernest Hemingway Home and Museum.
Not long after exiting the Margaritaville Key West Resort and Marina, we made a right onto Whitehead Street. The house is located on this street but you do have to walk a few blocks to get to it. You do see some great Key West sites along the way like other historic homes some famous like the Harry S. Truman Little White House and others that are not so famous but quite beautiful to look at.

The Ernest Hemingway Home and Museum
The house is very easy to spot on arrival. The cost is $15 per adult and $6 per child. Children five and under are free. It’s also important to note that admission is payable in cash only, credit cards are not accepted. Reservations are not needed and the house is open 365 days a year from 9 am until 5 pm. A 30-minute tour is included with the cost of admission. The tour is optional if you rather explore on your own. We decided to go with the latter but first, we took advantage of the beautiful shady trees and benches on the property. It was a very warm day and the rest was quite nice.


The house was built in 1851 and became the Hemingways’ home in 1931. This is the home that Hemingway lived in with his second wife, Pauline, and their two sons. The house still holds furnishings from when the Hemingways lived there including items that Pauline bought during her time in Paris and had them shipped to their Key West home.



The house is not the only attraction of visiting the estate but the lush grounds and pool are very beautiful. The pool was quite an undertaking and expense for the day. Hemingway was away during construction of the pool and left Pauline in charge of overseeing its construction. He became very exasperated over the expense of the pool and visitors are treated to a humorous story about Hemingway’s reaction to it.

I think my favorite part of visiting the home was the famous polydactyl cats we saw lazing about the grounds. Many of the cats are descendants of Snow White, the white six-toed cat that was given to Hemingway as a gift by a ship’s captain. He named all the cats after famous people and it’s a tradition that they continue to this day. We were able to meet the oldest cat on our visit who is a total sweetie named Harriet Truman.

It’s very obvious that the cats are well cared for and loved. They do ask that guests do not pick the cats up and I think it is important to be respectful of the kitties. The ones we came across that weren’t sleeping didn’t seem to mind a few pets. They were all very sweet and a memorable part of our visit.


Papa’s Pilar Rum Distillery
A few years ago the Hemingway Rum Company opened its Papa’s Pilar Rum Distillery and Tasting Room to the public. It is so named for Hemingway who was known as Papa and his beloved boat that was named Pilar. The distillery is located off of the corner of Simonton Street and Greene Street and is less than half a mile away from the Hemingway Home.

Our day in Key West was on a bit of a time limit and unfortunately, by the time we got to the distillery, we were unable to catch a tour in time before we had to return to the ship. You can book the 30-minute tours ahead of time online at $10 per person but I didn’t know how long our visit at the home would take which is why I didn’t do that.

However, we were able to participate in a free rum tasting! The distillery has two different rums. The Blonde Rum is quite buttery and actually reminds me of butterscotch. If I was to use either rum to make a rum cake, it would definitely be this one.

The Ultra-Premium Rum is a dark rum that is very smooth. The company created these rums to be sipping rums and do mention that if you choose to mix them that you should use Mexican coke because they are both made with cane sugar. You can purchase the rum at the distillery along with other merchandise.
Sloppy Joe’s and Captain Tony’s Saloon
I had planned to have a drink at Sloppy Joe’s but there wasn’t enough time plus it was a Sunday on a holiday weekend in the season so to say it was busy is an understatement. I have visited Sloppy Joe’s in the past and it’s a great place to enjoy a drink and listen to live music. We actually strolled right by it on our way back to the ship from the distillery. Things were really hopping, too!
Hemingway was known to frequent Sloppy Joe’s and actually, it was the original location that is now known as Captain Tony’s Saloon that he would have visited.
I feel that either location is a great way to say salute to Papa Hemingway and his incredible impact on history not only in Key West but the world.
Key West Aloe
I had a couple more quick stops to make on our way back to the ship that were also on Greene Street, not Hemingway related but worth mentioning. The first is the Key West Aloe shop. Our ship’s shopping guide mentioned it and I was interested in checking out their products. As someone who grew up in South Florida, I definitely understand the value of Aloe Vera. I found an unscented extra moisturizing lotion that I really liked and we bought a bottle of it to take home.

Key Lime Pie Bakery
When Derek and I first booked this cruise there was one thing I absolutely had to do in Key West and that was to get a slice of Key Lime Pie. The Key Lime Bakery was right next door to the aloe shop and I could think of no better place to get a slice of pie before boarding the ship. It was so yummy and a nice reward after all the walking we did that day!


I certainly enjoyed my time Following Hemingway’s Footsteps in Key West and visiting a couple of other places, as well. I hope that it will inspire you to seek out a similar itinerary on your visit to Key West!
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