Key West, Florida

Key West is the island and the city at the southwesternmost end of the roadway through the Florida Keys.

Key West is a beautiful destination, famous for water sports, lively nightlife, beaches and historic sites.

My boyfriend and I visited this city with an organized bus tour, as a day trip from Miami Beach where we were staying.

It took us almost two and a half hours with the bus to reach the island.

We passed by all the Florida Keys, with one stop at the Islamorada for coffee and breakfast.

The journey was amazing. If you like to learn more about Florida Keys and the roadway we passed by, called U.S. Highway 1, please check my previous blog post Florida Keys and Henry Morrison Flagler story.

In the bus we purchased from our guide the tickets for the Key West city trolley.

The bus left us at a parking, right a cross a street of Flagler Station Oversea Railway Historeum.

In 1905 Henry Flagler, one of the wealthiest men in the world, announced his plan to build a railway from Miami to Key West.

Some laughed, some scoffed, and most agreed that it could not be done.

After eight years, three hurricanes, fifty million dollars, and hundreds of lives lost, Flagler proved them wrong.

I suggest you to visit this museum while at the Key West, beacuse there you can learn a lot about the Key West Extension, and the tragic demise of Flagler’s dream in the devastating Labor Day hurricane of 1935.

As soon as we went out of the bus, this museum was our first stop.

Later on we felt thirsty so we walked toward the Half Shell Raw Bar for some beers.

This place is very famous and I have seen it many times at different photos and documentaries regarding Key West.

It is mostly known for their oysters dishes, but since we are not fans of oysters in general we did not tried any.

The bar-restaurant is located on the waterfront, next to marina.

They had very original interior design, since all their walls were covered with hundreds of license plates.

It was a really cool place with the great ambiance and great music.

We sat at the bar, and while we were drinking our beers we watched the man behind the bar how quickly and professionally he was cleaning hundreds of oysters.

It was an incredible experience, since it was the first time I watched something like this in my life.

We captured a few photos of the marina and we sat on the city trolley to make our round of the city.

City trolley is very charming, it reminded me of the old trams at Lisbon, Portugal.

Our driver was very informative and funny and he interacted with all the passengers including us.

He was very surprised when we said that we were coming from Greece.

He said that he is working as trolley driver for the last three years and that this was the first time he met someone from Greece.

The trolley had no windows so we were able to see the city and to capture some nice photos of the city and the beach from the trolley window.

We went down of the trolley at the Southernmost Point Buoy .

The line in front of it was very long. A lot of people were waiting to capture a photo in front of the buoy.

The large painted concrete buoy was established as a tourist attraction in 1983 by the city at the corner of South Street and Whitehead Street.

Today it is one of the most visited and photographed attractions in the United States.

Cuba is roughly 90 miles south of this point in Key West, although this was not originally on the marker, but rather on a smaller sign next to marker.

The paint on the buoy was damaged by Hurricane Irma in September 2017, but it was refurbished later that year by the original artist supported by the city of Key West which values the landmark as a tourist attraction.

But as you can see on the photos, I think it needs to be painted again, probably because hundreds of people are touching that buoy every day, some letters are already faded.

The Southernmost Point Buoy is an anchored concrete buoy in Key West, Florida, marking the southernmost point in the continental United States, the lowest latitude land of contiguous North American States.

Somehow we managed to capture the point itself, and we decided not to go back with the trolley, but to walk towards the center and explore the rest of the city on our own.

We continued walking through the Whitehead Street, towards the center.

The houses at the Key West are beautiful and colorful.

All of them were made of wood.

In general the historical Key West architecture is a major Old Town tourist attraction.

At Key West you are able to see an eclectic mix of over 3,000 wooden buildings dating from about 1886 to 1912.

This collection of 19th century structures is the largest historical district on the US Department of the Interior’s National Register of Historic Places.

Although Native American groups occupied the island for thousands of years, the modern era of settlement began in 1832, with Cuban immigrants, Bahamian fishermen, spongers, and wreckers, and New England natives building homes on the island’s western side.

The designs of these Conch Houses were influenced by Caribbean adaptations of New England sea coast, Greek Revival building traditions and the Gulf Coast shotgun house built by African and Haitian carpenters.

On the streets of Key West you can also see a lot of chicken walking around free.

We saw few iguanas as well.

Our driver and guide from the trolley said that there are so many iguanas at the Key West in general and they are everywhere.

Most of them in the city center can be found at the Key West cemetery where they are laying on the tombstones.

Some girls from our bus tour said to us how they went to the city cemetery last time they visited the Key West, because they wanted to see and capture the funny messages that are written on some of the tombstones there. Somebody suggested them to do so.

The girl said that there is phrase on a tombstone, written by the widow of the decedent that says: ,,At least I know where he’s sleeping tonight.” and some other funny phrases.

It seemed very funny to me, but we were not so interested in visiting the city cemetery, we were more interested in exploring as much of the city we could until the departure time.

On our way to the city center our next stop was the Key West Lighthouse.

We climbed to the top.

The view was breathtaking from the balcony.

Later on we paid a quick visit to the Key West Lighthouse museum and we moved on.

We intended to visit the Ernest Hemingway house, but the line for the tickets was so huge, so we just passed by.

We did captured few photos of the house surrounding though.

Ernest Miller Hemingway was an American novelist, short story writer, and journalist.

His Key West house is located at 907 Whitehead Street, across of the Key West lighthouse.

This was Hemingway’s home from 1931 to 1939, although he retained title to the home until he died.

Descendants of Hemingway’s original cats continue to live on the premises and you can see them everywhere around the property.


The house was one of the first on the island to be fitted with indoor plumbing and the first on the island to have an upstairs bathroom with running water, fed from a rain cistern on the roof.

I am very sorry we haven’t visited the house, but it was so warm outside and the waiting in the long line under the burning sun was out of the question.

But we did visited Hemingway’s favorite bar, the Sloppy Joe’s, for some ice cold beers though.

It was very crowded at the bar, with not even one empty table to sit.

Live music was playing on the stage.

I liked the atmosphere but since we couldn’t find table to sit and we got hungry and tired from walking around, after the beer we continued walking on the Duval Street in order to find a nice place for lunch.

We ended up at the Viva Saloon.

They had a beautiful garden where we found a nice table under the tree shade.

Their service was great, and the food we ordered was excellent.

At the garden stage a young man was playing the guitar and singing.

His repertory was amazing and I was so happy to hear some of my favorite Metallica songs among the other great songs he was performing.

At some point he noticed between the guests one friend of him, who was a saxophone player.

He invited him to play a few songs along with him. The old man was an amazing performer and everyone was amazed with his saxophone playing skills.

Later on the performer invited on the stage the old man’s wife, who was an opera singer by the way, but she refused with a smile.

When I cleaned up my plate, I ordered the famous Key lime pie to try it. The pie was very tasty, but the piece they brought was unfortunately very small. I could eat at least three of them.

This place was very charming and they had a kind of hipster style decoration.

I asked the owner if I could take some photos of the place. He said that I am allowed to do anything I want there.

He also revealed their secret ghost room on the second floor to me.

So I went up, I captured a few photos of the place, but I haven’t seen any ghosts, thank God.

There are a lot of rumors though that a lot of the old wooden buildings in the city are haunted, and they are the homes of raging occupants, souls who’ve never moved on.

The Travel Channel deemed Key West as one of America’s most haunted places.

If you are interested in ghost hunting and investigating locations that are reported to be haunted by ghosts, there are plenty of tours to visit the haunted houses of Key West. Check the link below to find out more about the Key West most haunted Locations. If you wish to book this tour and to see the price please press the word Viator.

After lunch at the Viva Saloon we walked a few hours around the city and the shopping area of Duval Street and Mallory Square.

Next stop was the smallest bar in the world.

We also visited the Key West Aquarium. You can find out more about our visit to the aquarium and our experience with sharks there in my next blog post, so stay tuned.

After the aquarium experience it was almost time for our departure.

We did some last minute shopping and we used the city trolley again to go back to the bus parking.

It was a really awesome tour in the most awesome town I have ever visited.

I have been in so many beautiful places in my life, but I never had the desire to live anywhere.

The Key West is the first place I have visited as a tourist where I truly wished that I could stay for the rest of my life.

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