Journey with Kileen

Journey with Kileen: The Florida Keys

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Hey, guess what? I have a new book out and it is available on Amazon! I write Travel Romance stories
 that are classified as “Boomer Lit.” They are romance stories for 50+ and the problems they encounter. The stories also read like travelogues. “Journey Beckons” takes place in the Pacific Northwest. “Journey To Port” takes place in Wisconsin and Michigan. And, my new one “Journey to The Tropics” takes place on cruises to both the Bahamas and the Yucatan Peninsula of Mexico.

In my new book, the ship stops at Key West so I thought that would also make a good travel article in case you are looking for a warm place to visit next winter.


The Florida Keys are a coral cay archipelago in the southeast United States. They begin at the southeastern tip of the Florida peninsula, about 15 miles south of Miami, and extend in a gentle arc south-southwest and then westward to Key West, the westernmost of the inhabited islands.

The islands lie along the Florida Straits, dividing the Atlantic Ocean to the east from the Gulf of Mexico to the west .As I mentioned in my St. Augustine article, Henry Flagler, an industrialist, began building hotels in St. Augustine in the late 1800s. His goal was to turn that city into an exclusive winter retreat. But, the temperatures were not as warm in northern Florida as they were in the southern part of the state. So he began building hotels further south, eventually all the way to Key West. However, there was just one problem; getting tourists to the island

Flagler had started a railroad which stretched from the Northeast states to St. Augustine to get his hotel guests to that city. Next he laid the railroad track that became the roadbed that put the Keys in easy reach. In that way, he could transport the wealthy Northerners to his hotel there.

Eventually a two lane road was built, which stretched one hundred thirteen miles on US Highway 1, from the Florida mainland down to Key West. The road was a marvel in the making with forty two bridges connecting the different islands. Key Largo (made famous by the Humphrey Bogart film and in song) was the island next to the Florida mainland in the upper keys. The road ended at Key West, the southernmost city in the U.S.

At the nearest point, the southern tip of Key West is just 90 miles from Cuba. The population is only about 25,000 but naturally that figure is higher when the tourists are in town. The island has long been a haven for writers and artists such as Ernest Hemmingway, Tennessee Williams and Robert Frost.

Naturally so close to Cuba, the island has been a refuge for Cuban political exiles. The island has also served as a base against pirates as well as a large salvage business from the many shipwrecks in the area.

When my brother and I visited the island, the shuttle bus from the ship dropped us at Mallory Square where you can catch the conch tour train. The trolley is a ninety minute narrative about the island and it is a good overview of the area. We saw both the old and the new Key West including Hemingway’s house, the waterfront, and a stop at a sign that said we were at the southernmost point of the United States

The island’s look reminds you of a coastal New England town but with lush vegetation as found on many Caribbean islands. As we rode the shuttle bus for the 10 minute trip to the downtown, we could see palm trees, hibiscus, and bougainvillea. The architecture is predominately Bahamian and the ship captains’ used wooden pegs instead of nails to build their homes. Living in a salt environment, they did not have to worry about the rust and corrosion that comes with using nails.


Today tourists flocked to the area for the beautiful sunsets and nightlife, as well as margaritas and key lime pie. But don’t forget to tour the Hemmingway house if you have a chance. The mansion was built in 1851 and Hemmingway bought it in 1931. The lush tropical garden, planted by the author, is home to more than fifty cats descended from the author’s felines. No worries about rats or mice getting into that house. And you can see a penny embedded in the concrete at the head of the pool. Hemmingway supposedly did that when he found out what the pool would cost to install. When you visit, you can almost picture the author sitting in his house writing “For Whom the Bell Tolls,” as he watched his cats running around in the yard.”

In the evening you can take a ghost tour and hear all the legends of hauntings and shipwrecks. And just before sunset, everyone flocks to Mallory Square to watch the various street performers. Musicians, jugglers, and contortionists vie for the attention and donations of the spectators gathered to watch them.

That seems like a great way to make a living. Be sure and have a margarita in hand as you wait for the sunset. There are also several museums you can visit or even go diving on some of the shipwrecks in the area. Just remember, when you are there, you are on “island time.”
Editor's note:
 To read in depth about the Seattle, WA area, check out Kileen's book, “Journey Beckons.” You can order it through her website (as well as preview the first few chapters) at or you can order it through Amazon either in book form or the kindle edition. 

Happy to say that Kileen has been very busy. Her latest book, “Journey To Port” is now also available through Amazon/kindle, and it's also in book form through Amazon. Also, on her website (, you can both preview a few chapters as well as order the book.

Ohhhhh my.  Kileen is hitting a “home-run” again!  Just released: “Journey To The Tropics” in which she explores love the second time around – all set within lush environment of the Bahamas!  Enjoy – and visitAmazon to get your copy! 

Kileen Prather has been a Tour Manager since 1997. Her exciting career takes her to between thirty-five to forty states a year. According to Kileen, there aren’t too many places in the US that she hasn’t visited. She absolutely loves traveling and meeting so many wonderful people from all over. In her column for After Fifty Living, Journey With Kileen, she shares her favorite places and talks about the different means of travel, whether you care to go by car, boat, train or motorcoach (bus).

Kileen is also the author of five books. If you’d like to learn about the Seattle area in depth, check out her book, “Journey Beckons.” You can order it through her website (as well as preview the first few chapters) at or you can order it through Amazon either in book form or the kindle edition. Her latest book, “Journey To Port” is now also available through Amazon Kindle. You can preview a few chapters of this book, also, on her website (

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