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Plan Your Visit to Key West, Florida

Plan a Trip to Key West, Florida

On our first visit to Key West, Florida, the southernmost city in the United States, we arrived by cruise ship. Unlike a good many of our fellow passengers, we didn’t head for Duval Street to start drinking at 10:00 a.m. No Sir. Mister and Mrs. Excitement went on a wholesome bicycle tour.

On our most recent visit to Key West, we drove down from Miami for a two-night stay. We enjoyed the ride on Route 1 South, the picturesque Overseas Highway.

Key West sunset from Mallory Square

Sunsets are a deservedly big deal in Key West, Florida.

The Overseas Highway is a “there there” unto itself. It traverses the east coast of the United States from Florida to Maine, all the way to Mile marker zero. Keep going and you’ll get wet.

conch republic flag

By Jmckean (Own work) [CC BY 3.0 (], via Wikimedia Commons

That Key West Vibe

Key West, Florida, prides itself on “keeping it weird”. From time to time Key West threatens to secede from the United States as the Conch Republic. The most recent talk of secession was in 1982 in response to a U.S. Border Patrol blockade of U.S. Route 1, threatening Key West’s vital tourism industry.

During our visit to Key West, it seemed to be a mixture of:

  • the French Quarter and the Garden District in New Orleans;
  • the quaint Victorian seaside town of Cape May, New Jersey;
  • the gay friendly Delaware River artist town of New Hope, Pennsylvania; and,
  • a sprinkling of aging hippies displaying varying degrees of attention to personal hygiene; with,
  • occasional flyovers by fighter jets from the Key West Naval Air Station.

Singer Jimmy Buffet’s association with Key West has also given it the appellation “Margaritaville”. The opportunity to consume margaritas, and probably every other alcoholic beverage, is available pretty much 24/7.

This is especially true along bar heavy Duval Street, Key West’s version of New Orleans’ Bourbon Street.

Things to Do in Key West, Florida  

Key West house

A Key West house surrounded by lush tropical and subtropical vegetation.

We only had an afternoon, one full day and two nights in Key West. The city and area are worth a longer visit. For example, we did not have time to sample any of the outdoor activities in and around the water.

If your visit is as short as ours was, I can recommend the following Key West activities:

A Walking, Bike or Conch Train Tour of Key West

On your first visit to Key West, I would recommend taking a walking tour, a bicycle tour or the popular 90 minute Conch Tour Train so you can learn some history and identify places to which you want to return for a more in depth visit.

We used the afternoon of our arrival for a walk around town. Indeed, “walking around”, looking at the restored houses surrounded by lush tropical vegetation is a bona fide visitor activity.

A typical shotgun style Key West house.

A typical shotgun style Key West house surrounded by colorful bougainvillea.

Ernest Hemingway’s House in Old Town Key West

A typical shotgun style Key West house.

Ernest Hemingway’s home in Old Town Key West.

We tried to visit Harry Truman’s Little White House, but were thwarted by a power failure. Instead, we made our way to the Old Town Key West home of raconteur author, Ernest Hemingway.

During our visit to the Hemingway Home Museum, the adult admission fee was $13 which included a half hour guided tour. We were  also free to wander the house and grounds independently.

The home was decorated by Hemingway’s second of four wives and the house retains much of the Hemingways’ furnishings. “Papa” lived there from 1931 until 1940 when he decamped to Cuba.

The house and grounds are also controversially home to over 40 descendants of Hemingway’s six-toed cat. Some feel the cats are exploited by being “on show”, but they wander at will and seemed well fed and very content to me, especially the three napping on Hemingway’s bed.

Victorian Home with Wrap-Around Porches on Two Stories, Key West Florida

Victorian Home with wrap-around porches on two stories in Key West Florida

The Mel Fisher Maritime Museum in Old Key West 

I feared the Mel Fisher Maritime Museum had the potential to be cheesy, but we paid the $12.50 admission fee and an extra $2.00 for the audio-guide and were pleasantly surprised.

Mel Fisher was an underwater salvager who after many expensive years of searching, discovered the 1622 wreck of the Spanish treasure galleon Atocha. He prevailed in a protracted litigation with the State of Florida over to whom the treasure belonged.

If you are interested in underwater archaeology and colonial Spanish history, you will find this to be a well curated, interesting museum.

In a disconcerting juxtaposition, during our visit, the upstairs had a Harry Potter exhibit next to an exhibit explaining the horrific slave trade.

The Old US Customs House in Old Town Key West

The 1891 US Customs House in Old Town Key West is now a museum.

The U.S. Custom House Museum in Old Town Key West

We were drawn to a building just off Mallory Square resembling the 1897 administration building at our New England college designed by architect H.H. Richardson.

We were told that the Key West building, unlike any other in town, was indeed designed by Mr. Richardson in 1891 as the United States Custom House and government office building. (I knew my Art History 101 course would come in handy some day!)

Today it houses a museum showcasing local artists downstairs and dedicated to the history of Key West upstairs. There was a first rate video about the Overseas Railroad to Key West, destroyed by a monster hurricane in 1935.

Admission was a modest $7.00. Actually, we only paid $6.00 because we were “carded”; that is, we were asked if we qualified for the AARP discount. We did. Ouch!

Visit Mallory Square for the Sunset Celebration  

Any visit to Key West, Florida should include a Mallory Square Sunset Celebration. Each evening, tourists and locals gather at Mallory Square to watch the sunset over the Gulf of Mexico. There is entertainment by all manner of street performers.


You won’t go hungry. In addition to the many restaurants in the Mallory Square area, there are street food vendors.

Where to Eat in Key West, Florida

Bliss Key West is the new name for the restaurant where we enjoyed dinner our first night in Key West. In addition to the new name, it has a new location. However, it is still owned and operated by the same Colombian family and is described as seafood and Latin fusion.


The restaurant where we ate dinner our second night in Key West which was then #1 rated on TripAdvisor seems to have completely disappeared.


Given the rapid turnover in restaurants and chefs, I recommend using TripAdvisor, Yelp or OpenTable to find current information about restaurants whenever you are visiting a new city or town and don’t personally know any locals who can provide recommendations.

Where to Stay in Key West, Florida 

Key West is a very popular year round vacation destination. In order to have your choice of accommodation, reserve something as far ahead as possible.


We often enjoy bed and breakfast establishments. At breakfast, we usually glean a lot of useful information about the locale from the owner and other guests.


For Key West, I used TripAdvisor to find a bed and breakfast inn in a mostly residential area, some seven blocks off the main shopping/drinking area of Duval Street. The Artist House on Fleming is a restored 1896 house.


Our second floor room required us to use an outdoor staircase (slippery when wet) and opened onto a shared porch, overlooking the rear garden and a whirlpool. While the setting appeared charming and tranquil, some of our fellow guests — not so much. Their nocturnal comings and goings were readily audible.


Breakfast was self-serve continental with tables on the outdoor back deck. With a rear-facing bedroom, breakfast chatter was not conducive to staying asleep. (OMG, I realize that this makes me sound like a curmudgeonly Baby Boomer traveler.  I admit that we are addicted to our white noise smart phone app when we travel. Please don’t roll your eyes.)


As a popular tourist destination, Key West has accommodations of every type, at every price point. Figure out what features are most important to you (i.e.: location, quiet, amenities, etc.) and use a hotel booking engine to read reviews. Either book online or call the establishment directly if you have specific questions or even to be able to sometimes negotiate a price.

Key West sunset from Mallory Square

Don’t forget to spend sunset at Mallory Square.

As it did for us, I’m sure a two night visit to Key West will be enough to convince you that two nights isn’t long enough and you need to return to the Conch Republic.

Have you been to Key West? If so, do you have an recommendations for planning a trip there? If not, do you think it is worthy of a place on your travel bucket list?

Read more of our travel content! Here’s what to do in Santa Fe, New Mexico, and our recommendations for indispensable travel accessories.

Suzanne Fluhr, Travel Editor

Suzanne Fluhr, Midlife Boulevard's travel editor, is a recovering Philadelphia lawyer, empty nester, wanderer, dog person and Zentangle® enthusiast. She also writes about Baby Boomer travels for the body and mind on her personal blog, Boomeresque. Instagram: Boomeresque2

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Thursday 13th of July 2017

Never been to Key West and honestly, I'm surprised there's so much to be seen there. I'll definitely consider it for my next vacation, thank you!

Sharlyn Lauby

Tuesday 20th of June 2017

The Truman Little White House is an interesting tour. Banana Cafe serves fabulous crepes.

Suzanne Fluhr

Tuesday 20th of June 2017

I was looking forward to visiting the Truman Little White House. Unfortunately, they were having electrical problems the day we were there. I guess we'll just have to go back. :)

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