Key West, Florida – A World Away

Key West, Florida – A World Away

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On a recent kayak trip to Key West, Florida, our guide told us he is frequently asked if they accept American money.  Really?   Although this funky little town is definitely part of south Florida, we could see why someone might think they had left the country for the tropics.    Don’t be surprised to find palm trees (and free roaming chickens) on every corner. Many of the homes are plantation style with wide overhanging roofs and big doors inviting any breeze to enter.  The days are warm and sunny and after an afternoon nap, the town comes alive in the evening with Caribbean music and food.  Key West is definitely a world away; closer to Cuba than Miami.

The town has always been a laid-back refuge for writers, painters and pirates, fishermen and now tourists.   The Ernest Hemingway House is right downtown.  Other residents include Tennessee Williams, Elizabeth Bishop, Robert Frost and Jimmy Buffett and the Margaritaville Bar.

Florida, Key West Hemmingway 2


With a wide multicultural base, Key West has the perfect blending of African heritage, Cuban, Bahamian, Spanish and English.   The downtown seaport has several fine museums – our favorite had a wonderful display of Hemingway’s story “The Old Man and the Sea” on the huge staircase.  This area is crowded with t-shirt shops and bars who cater to the huge cruise ships that come and go every day.   It’s rather like an adult Disneyland.

Key West shop
Key West shop

We couldn’t help but think what it would be like to live here and this is what we found:

Population: 25,000 full time residents.   The city swells to 45,000 during the snowbird winter months when the warm weather calls the retired folks from the north.  And 12.8% are over 65.  You will also find tourists from all over the world. 

Weather:   While the winter months make Key West extremely popular with the temperature in the low 70’s – the summers are hot and humid with an average 55 days with temperatures in the 90’s F.   Can you say “hot and muggy?”  The other big weather issue is hurricanes, although they rarely have a direct hit.   Hurricane Wilma hit in October 2005 and the resulting storm surge flooded Key West with 3 feet of water, destroying homes and businesses.   It doesn’t happen often, but it does happen.  The most temperate months are March, April and May.  There is a higher risk of hurricanes from August through December.

Crime:  Here’s the bad news.   Both the violent crime rate and the property crime rate are well above the rest of Florida and almost double that of the United States.  If you consider buying a winter home here, we recommend a gated community or condo with a good security system.

Housing:  Although there are dozens of homes well above the $1 million range, you can still find homes below $300,000.   Condo’s are not much different.   The selling price is dependent on the view, the amenities, and location (of course).   This is not a cheap place to retire.  

House listed on Zillow
House listed on Zillow

We found this one bedroom, one bath house on Zillow for $385,000 with $2,100 a year in taxes.

But there is so much to do here besides just laying around in the sunshine!   You can find world class fishing, historic sites, museums and galleries.  There are kayaking and snorkeling sites, the Dry Tortugas National Park, dozens of events and festivals.

We even spent a very entertaining afternoon at “Peppers of Key West” where we sampled hot sauce till we couldn’t take it any longer.   A fun shop with informative staff.   The habaneros jelly beans did me in!   (Hint:  the saleslady gave us yoghurt to cut the hotness before we melted into the floor!)

Whatever you do, go down to the beach and watch the sunset.   What a gorgeous site!

 Cover Photo By gabe popa via

Zoom in and out on the map below to see Key West and the surrounding area!





Cheryl and her husband have just recently retired and live in the Pacific Northwest. She has been enjoying her herself by traveling around the world, playing with her grandchildren, and she frequently volunteers in her community. There is certainly never a dull moment with Cheryl. She cheerfully co-founded RetireBook and wants to share her energy, hoping that it inspires her readers to live life at its fullest.