Visiting Key West is almost like visiting a foreign country.  It is different from main stream America.  Walking down Duval Street you may hear 10 different languages.  It has truly become an international destination. 

Then, too, Key West is famous for its liberal life and accepting attitudes. There is something for everyone at the “Southern Most” land.  Even now the famous show, “The Price is Right,” is giving away vacation packages to this 4-mile-long island.

I remember traveling to Key West in the 1960’s with my parents.  We three kids were treated to a fine pool along the ocean at “The Southern Most Hotel.”  My dad always loved swimming. I believe the cost back then was $60 dollars.  Today, those rooms go well over $300.

When you enter into the island of Key West, you will have to make a decision either to turn right along North Roosevelt Blvd, or left along South Roosevelt Blvd.  We like going left as the ride is along the ocean.

A popular way of getting to Key West is taking a plane.  The airfield is east of downtown and it is noisy with the 727’s flying over. 

Then, too, a Naval Station is about five miles away.  Most every day you can witness jets flying over. There are about 5,000 people incorporating service personnel and families in Key West.

There are also ferries from Fort Myers and Marco Island daily.

Then, too, many cruise ships stop for the day.  Voters in Key West have limited the number of people disembarking from cruise ships to 1500 a day.

There are plenty of places to stay in Key West.  Although prices are at times the highest in the nation. Many people stay in Bed & Breakfasts near downtown.  We have found a budget place on the southern end of the famous Duval Street, The Blue Marlin Motel. The AC is cool and it has one of the largest pools in Key West.  Book well ahead for the best prices. 

One year (1989) we even booked a walk-in rate ($89) at the exclusive Reach Hotel.  By far, that was the largest room we ever have had. 

Kathie and I have visited Key West numerous times in all the seasons. We love biking around the island.  The trail/sidewalk is about 9 miles around. Our first biking trip was in 1986.

One of the places we stop and take a “look-see” is the resort of Casa Marina.  It is a 4-star hotel with two pools. 

At Higgs Beach, there are free tennis courts and now even pickleball courts.

Close by is the African Refugee Cemetery at Higgs Beach.

We enjoy going out on Edward B. Knight’s Pier.  One can catch a superb sunrise here.

Going south, you will come to the sign where US1 comes to an end—or the beginning. It does make a good picture.

 

Technically, this is where US1 comes to an end, or even the beginning. It is referred to as Mile  “0.”

Not far is the Southernmost Point Buoy. It is one of the most photographed points in the USA.  The Buoy was established in 1983.  It is hard to imagine, but this buoy is 18 feet above sea level.  The buoy is considered the southernmost point in the contiguous USA.  At this juncture, Cuba is but 90 miles away directly south.

Now, if you go west 70 miles you will hit the Dry Tortugas and the National Park of Fort Jefferson. 

To protect the gateway into the Gulf of Mexico, Ft. Jefferson was established in 1846.  The boat out of Key West, Yankee Freedom, will take you there in just over two hours.

If you get sea sick, there is always the plane.

There is good snorkeling around the fort.  It is not very large being 47 acres.

Walking in and around the fort gives you a feeling of being in the past. This was the place where Dr. Samuel Mudd was placed after being convicted on helping John Wilkes Booth mend his broken leg after shooting Abraham Lincoln.  His cell is well marked.

When we were there in 2014 a number of Cuban refugee boats still could be seen.

There is a feeling of being isolated while walking the halls. Some people actually seek this isolation as you can actually camp by the fort.  There are bathrooms and water supply. 

Park Rangers live at Ft. Jefferson.  Ironically, Fort Jefferson became obsolete quickly with the rise of bigger and better canons. Those bricks would not stand up to a naval bombardment.

The actual southernmost point of the contiguous USA is around Fort Zachary Taylor in Key West which is a “paid” State Park.   On the other hand, the southernmost point for the entire USA is on the Big Island of Hawaii.  We have, also, been there.

In 2007 as we were going down this one-lane road, we came across this dilapidated wind farm going to the “Southern Most Point” in the USA.

Fort Zachary Taylor was one of only three forts not taken by the Confederacy during the Civil War (Fort Jefferson in the Dry Tortugas and Fort Pickens in Pensacola being the other two.)

Fort Taylor is a State Park and well worth viewing. Beautiful vistas of the sea can be had on top of the fort. 

Down Whitehead Road is where Ernest Hemingway once lived for 8 years. 

He came to visit and loved it so much with his second wife, Pauline Pfeiffer, they decided to buy a house up for auction.  The largest lot in Key West was paid for by Pauline’s uncle for $8,000 plus back taxes.  

There is a separate cottage where Hemingway wrote such works as”For Whom the Bell Tolls”, “Death in the Afternoon” “The Green Hills of Africa” and “The Snows of Kilimanjaro”.

The twenty-minute tour (a pricy $17 for an adult ticket) is well worth the effort if you have any interest in Hemingway. 

The recent Ken Burns video documentary does a thorough review on his life. There are many stories about Ernie, just one too many for this expose.  The stories that I most remember are:

1. Ernest would indulge in adult beverages. He would find his way home by using the lighthouse which is literally opposite his home.

2. Paved streets were placed on Whitehead in the early 1930’s. Ernest and his friends used the old Baltimore bricks to build the wall that surrounds his home.  If you look at that wall, it was definitely done by amateurs!

3. There are 58 cats that live at the homestead. Half of them are polydactyl cats. Apparently, the family’s favorite cat, Snow White, propagated the feline family back in the 1930’s.

4. Ernest loved fishing off his boat, The Pillar. He would write my favorite work, “The Old Man and the Sea”.  It was also reported that he went out on the Pillar looking for Nazi submarines. 

5. Pauline almost broke Ernest bankbook while he was in Europe.  She built a $20,000 pool ($400,000 in todays monies).  The pool is 24 feet wide and 60 feet long. When he saw the pool, legend has it that he tossed a penny on the porch and said, ” Pauline, you’ve spent all but my last penny, so you might as well have that!”  She later clued that penny on the porch. 

Not far from Hemingway’s, is Harry S Truman’s “Little White House”.

There is a “free” tour through this famous home where Truman made 11 visits totaling 175 days. In fact, Key West became a famous jaunt for Presidents Eisenhower, Kennedy, Carter and Clinton.

 

Another way to see Key West is through the “Conch Train”.  We have taken it once and found the ride to be informative.

 

One of the places the Conch Train visits is the famous Key West Cemetery. There are 100,000 people buried at this place. Members of the USS Main crew are buried here too.  They died when the USS Maine blew up in the Havana Harbor killing 260 sailors.  Their deaths help trigger the Spanish-American War of 1898.

Close to the cemetery is “Poor House” Lane.  No longer poor as real estate prices, like everywhere else, has exploded in Key West.

You may have a chance to see some unique cars in Key West. The Pink Taxi is quite interesting and still in service.

For several years, we have traveled to Key West in early November to witness the International Boat Races.  Days before the races, these large boats are trailered down the Over Seas Highway.

There is intensity which is hard to describe.  The fast moving speed boats with the roar of their engines is quite mesmerizing. 

The boat races do bring in the party revelers with their large boats and yachts.

Duvall street is the main avenue in downtown Key West.  This is where most of the action takes place. There are interesting buildings you would never see anywhere else. People sometimes refer the street as “The Duval Crawl.”

There is a number of tee-shirt shops.  My favorite tee says:

At New Year’s Eve, they drop the Red Slipper. We were in Key West over one New Year’s Eve.  We fell asleep by 9:00PM, truly.

Near Halloween, Key West has “Fantasy Fest.” It is a 10-day party–with few clothes–that was started in 1979. There are as many as 75,000 revelers.  We came down in the early 2000’s.

A most vivid memory of Fantasy Fest was almost being seen by one of my volleyball players, Kelly Hemberger.  She was down visiting the festival with some of her girlfriends.  I never disclosed of seeing her that day.  When I first saw Kelly as an 8^thgrader, I thought Kelly had the most beautiful face.  That face later turned up later on Playboy as Kelly Carrington.  I honestly never did look at that issue, truly.

Halloween is a special time in Key West.

 

There are quite a few establishments and shops.  There is even a Robert Wyland gallery.  Robert Wyland has done 100 murals, mainly depicting Whales, around the world.

The place that seems to draw the most people is the famous “Sloppy Joe’s Bar”. 

Every time we pass that place it is always crowded and seats are limited. Ironically, we have never been inside, truly.  

 

Once a year there is a contest at Sloppy Joe’s for the Hemingway look-a-like contest.    I hope my friend, Bruce Wells, enters that contest one of these years.

Nor have we gone into Capt. Tony’s Bar, the other bar that Hemingway actually went into. The actual bar that Hemingway frequented maybe in in Havana, Cuba.  Ernest loved Daiquiri’s.

Close by Sloppy Joe’s is a popular bar called “Irish Kevin’s.” This is a favorite of Brian Wheatley ( Venice HS. Volleyball Coach)  and wife who loved this place.  We did go inside and listened to a superb rendition of “West Virginia.” 

 

Another place we have never visited is Mel Fishers’ Heritage Museum. An early picture (1989) of us outside the museum.

Mel and his crew discovered the shipwreck Atocha with treasures worth over $400 million dollars.  The Atocha was 35 miles from Key West.  Mel Fisher made Key West his home.

The museum is today a non-profit identity named after its founder, Mel Fisher.  The museum houses a Conservation and Archaeology lab. There used to be a gold bar exhibit where people could actually hold it.  Two thieves lifted the bar in August of 2010.  At present, the bar worth $550,000 dollars and the theft remains unsolved.

Over the years, we have met interesting people where the Rainbow Begins (or ends for that matter).

There are plenty of good restaurants in Key West.  We have enjoyed Cuban food at El Siboney’s Restaurant.  For some reason, there is an Indian Chief statue in the middle of the establishment.

We have also enjoyed The Conch Republic.  Fried Conch with the tasty marmalade is a sure bet.  I also like their Blackened Chicken sandwich.

It is by the Conch Republic docks that one can catch snorkeling and sunset cruises. It seems a company called “Fury” dominates the market. There are other vendors too that take people out, even to kayak.

A pricier establishment is Louie’s Backyard. Situated in a residential neighborhood, most of the restaurant faces the sea.

 

The Boat House is the best Happy Hour in Key West.  Plenty of food and discounted adult drinks.  They have moved and taken over what was Turtle Kraals.

 

One of the newer Key West Restaurants is Wahlburgers.  Our verdict is still out. 

Near Mallory Square is Bistro 245.  As we watched the boat races from this vantage point, Kathie enjoyed their fruit plate.

 

Another favorite place is taking the free boat over to Sunset Key and having lunch (a bit pricy) along the water at the Latitudes restaurant.

Sunset Key is exclusive with high end homes, many for rent.  Even Oprah Winfrey rented all the cottages for her 44^th birthday back in 1998.   The free boat ride does spark an ambiance to the place.

Book a month or so in advance if you ever want to go. The place has become a favorite for many.

Close to where you catch the boat to Sunset Key is Key West Museum of Art and History.  We have always enjoyed the large statues outside the museum.

You have not visited Key West until you go to Mallory Square and see a sunset or even the street performers. The Square was named after a 19th century US Senator, Stephen R. Mallory, who later became the Secretary of the Confederate Navy. A side note is Mallory’s Father-in-law sired 27 children and 127 grandchildren.  Mallory would have 9 children, two of which died frighting for the Confederacy and the third son became a general. 

The street performers are good as they actually have to get a permit.  These performers rely on the generosity of the bystanders.  This past time we enjoyed “Blue” and how he entertained everyone.    

At times, Mallory Square can get quite crowded.

Sometimes the sunsets are a hit or miss proposition.  When the time is right, these sunsets are spectacular.

It was when visiting a sunset that we came across “Jimmy” from Philadelphia.

Jimmy worked a kiosk making the best Strawberry Daiquiris.  Any excess, Jimmy gave the daiquiri to you in a cup.  Jimmy made it on the morning travel segment on NBC with Matt Lauer and Al Roker circa 2010. He was quite proud of those moments. Jimmy was a good soul.

Visiting in 2021, we found out that Jimmy passed away in 2019 with Melanoma.  RIP Jimmy.

It seems anyone who travels to the Key West has their special places to eat, stay and visit. We wanted to share some of our happier memories to this very special place under the sun.

Thank you for reading our post.  We dedicate this post to “Jimmy.”