Strolling through Key West: a walking guide to the Southernmost city in the continental U.S.

Key West is the Southernmost city in the continental U.S., the point where the North begins: Mile 0. As the name suggests, Key West is also the westernmost of the inhabited islands, which, along with all the other keys located off the southern coast of Florida form a coral key archipelago, known as Florida Keys.

Mile 0, Key West
photo credit: Google

The name Key West is actually a misnomer. Spanish settlers originally called Key West as Cayo Hueso, meaning Bone Island, referring to the bones of the Calusa Indians who had once lived in the Florida Keys. English speakers mistook Cayo Hueso, thinking it sounds like Key West.

Conch Tour Train

You have several options to sightsee Key West: either to rent a bike, or a scooter, or to use one of the local tours: the Hop On Hop Off Trolley, or the Conch Tour Train. But we rather wanted to have a walk through the city, and experience the city streets the way we like.

Heading out from the ferry straight on Grinnell St was the easy part. Our itchy feet were more than ready after a 4-hour ride from Fort Myers.

Key West City Cemetery was right ahead, in the center of the town, and is very famous for the sense of humour exhibited by the gravestones. The big conch monument captured our attention from outside the fence, and we wondered what they are.

Key West City Cemetery

Conchs aren’t just the pretty pink seashells. In Key West, conchs are people born here. You are not considered a conch (pronounced konk with a hark ‘k’) by simply living here. If you’ve been a local at least 7 years, then you might be considered a ‘freshwater conch’. Only the locals born in Key West are considered a “seawater conch”.

We were impressed immediately by the lush vegetation along our way, the intriguing homes, courtyards, and gardens. You can easily forget your direction, but we had to stick with our plan to visit the Ernest Hemingway home and museum, the former residence of the famous author, where he lived from 1931 to 1939.

You can wander around by yourself, or can register and wait for a guided tour to visit the house and the courtyard. The estate is quite small, and the charming six-toes cats are for sure the stars of this property. More or less shy, they won’t let them be photographed so easily. Beside the staff designated for this museum, there are four additional people hired specially to take care only of all the 50+ cats!

Polydactyl cat, Hemingway museum
One of polydactyl cats from Hemingway museum

If you like lighthouses, and willing to climb 88 steps, there it is the Key West lighthouse, right across the street from the Hemingway Museum, behind the trees. Following the destruction of the first Key West Lighthouse during the devastating Havana Hurricane in 1846, a new one was built at the present location in 1848.

Key West Lighthouse

Known for it’s “One Human Family” philosophy and motto, Key West is famous for so many other things. Part of the big local family are also the chickens that roam freely on the streets. All chickens but especially the roosters became the mascots of the city, a good, healthy stock of them spread throughout the whole city. And it’s been this way for decades. Some people find them a nuisance, others charming. But doesn’t matter which category you’re in, just be prepared to hear a rooster crowing at anytime during the day!

Rooster, Key West

For the ones looking for a Happy Hour, guess what! While most of the Happy Hours are in the afternoon, you will be able to find specials through out the day, and can have a Happy Hour all day long!

Happy Hour

One of the most popular attractions in Key West is the concrete replica of a buoy at the corner of South and Whitehead streets, erected in 1983, claiming to be the southernmost point in the continental U.S.

the southernmost point in the continental U.S.

If you are so keen to have a picture with this monument, then you need some time and patience to wait in the long line. The queue wouldn’t be very long, but it’s moving very extremely slow. Instead, we took a couple of pictures from the concrete ledge from nearby, like the rest of the people who wouldn’t have the desire to wait for so long.

Fort Zachary Taylor Historic State Park is the terminus point of the island famous for the best beaches of Key West, several nature trails, bike paths, and the fort itself, but we didn’t have time to visit this time. Passing by the Truman Waterfront Park, we followed Emma St, which turned into Front St pretty soon. Stylish houses emerged on both sides of the street, following later some historic buildings and markers. Generally, the structures date from 1886 to 1912, and they distinguish by their side-hinged shutters, and covered porches.

Another important landmark along our way was Truman’s Little White House. The house was built as quarters for Navy officers in 1890, but became famous because of President Harry Truman, who used the site for working vacations between 1946 and 1952.

Used as a command headquarters in three wars, the house was later used as winter White House by several US presidents, hence it was listed on the National Register of Historic Places in 1974. Unfortunately, when we arrived, the Little White House was closed for visitors, as a private event was just taking place in the big courtyard.

Truman's Little White house

We followed Front St, turning left at the Key West Museum of Art and History,

Key West Museum of Art and History
Key West Museum of Art and History

heading straight to a large seafront,

Seafront, Key West

which took us to Malory Square market.

Malory Square Market

If you like watching sunsets, then Mallory Square is the place for you, as it offers the best spot you can watch the sunset from.

The sea and the story of Key West are entwined with stories of treasure ships and merchant vessels that fell victim to treacherous reefs and hurricanes. Even more deadly were the pirates who stacked their prey with abandon until the arrival of the US Navy in 1823. Key West was once the richest city in the U.S. per capita. The wreckers would make their fortune by auctioning off or reselling the valuable cargo they would save.

This month, Key West is celebrating 200th anniversary of this permanent settlement, and the ones who happen to be there on March 25th, will have a chance to participate in a lot of activities, including a parade along historic Duval Street.

Following the Historic Seaport Harbor Walk is a must for those who love the seaside. For almost two hundred years, the Seaport has been a focal point for much of the economic and cultural life on the island. If you are there around 4 pm, the fishermen will clean their catch of the day, and the brown pelicans will enjoy the free dinner for the tourist’s enjoyment.

Harbor walk - brown pelicans
Harbor walk - brown pelicans

Several restaurants display mouth watering dishes on the patios along the way, a wonderful choice if you are ready for dinner. If not, then you can go ahead immersing into the perfect place you can spend an evening, a vibrant place where hundreds of boats are ready to take you on a sunset cruise with live music.

Seaport, Key West

So hard to say good bye, isn’t it?..

Do you like walking? Then you might like Jo’s Monday walks too!

How to get there:

  • By car – being surrounded by the sea, the only connection of Key West with mainland is by U.S. Route 1, the longest north-south road in the United States;
  • By ferry – from Fort Myers, or Marco Island;
  • By bus – Greyhound Keys shuttle has a daily scheduled departure from the Miami airport to all areas in the Keys;
  • By boat – if you’re a sea person;
  • By air – private charters are made available for small groups of people.

Where to stay:

  • The Old Town is the best option for a traditional Key West vacation, as all the points of interest are very close;
  • If you do not mind the longer distance to the most sought places on the island, then the New Town is another option;
  • There are also few campgrounds around Key West;
  • Keep in mind that Key West is a major touristic place in southern Florida, therefore very pricy. You might want to book in advance your stay for better options.

Things to do:

  • Fishing is one of the most appreciated sports around these waters. Not only the pictures hanging in the museums with big trophies are a proof, but the big fish we spotted in the Seaport waters were more than impressive;
  • From biking, kayaking, diving, snorkeling, to visiting all sort of museums, bars, and restaurants, Key West lifestyle sparkles with exuberance. The Happy Hour becomes Happy Day, and the nightlife never has shortage of fun or live music.

Interesting facts:

  • Key West is closer to Cuba than to Miami;
  • The Overseas Hwy that connects the mainland to Key West was completed in 1938, and connects a string of keys and coral rock with 113 miles of concrete roadway. There are 42 bridges along the way;
  • The Railroad arrived in Key West in 1912, and operated from 1912 to 1935. It was mostly destroyed during the devastating hurricane of 1935, often called the storm of the century;
  • Forty-one degrees F is the record low temperature in Key West. That means 5 Celsius. This occurred twice since temperatures were recorded starting in 1873: on Jan 13, 1981, and Jan 13, 1886;
  • Key West is home to the third largest barrier coral reef in the world. Known as Florida Straits, Key West’s coral reef extend 150 miles north towards Miami, and 70 miles west to the Dry Tortugas. It’s the largest in North America, and the third largest in the world (behind Belize and Australia);
  • Duval street is a mile long pub crawl, lined with more restaurants, bars, and shops than you can count;
  • Key West is often referred to as the Conch Republic. This is because in 1982 the citizens advocated and tried to secede from US as a revolt against the US border patrol, who set up a roadblock and inspection at the entrance to US1 Overseas Hwy for illegal immigrants and narcotics. Today, the Conch Republic Independence takes place every April with tongue-in-cheek celebrations and parties.

Tip(s) of the day:

  • Make sure you’re getting a map from a local tour station, or during the ferry ride;
  • Get your camera ready, and fully charged;
  • Comfortable footwear is recommended, and lots of sunscreen on your walks;
  • Make sure you book in advance your ferry if this is your option;
  • For local tours, make sure you’re checking the website for rates and discounts;
  • A minimum 2 full days are advisable for maximum sightseeing;
  • The best time to visit Key West is between March and May. The weather is still similar with the one over the winter, but it is not as busy and pricy as in the winter time (November to February).

~ visited in February 2022

28 thoughts on “Strolling through Key West: a walking guide to the Southernmost city in the continental U.S.

  1. Oh, the Conch Tour Train sounds like fun … but you’re right, walking is definitely the best way of exploring a town/city! Chickens walking freely in the city’s streets and ‘Happy Hour’ throughout the day – Key West certainly sounds like a unique place 😊. And what a lovely seafront … you’ve captured so many beautiful pictures that this post was truly a feast for the eye!

    Liked by 1 person

    1. The tour train tickets were actually on sale on the ferry, but our stay was too short to risk spending much time on the tours. Next time😊 As for the pictures, so hard to select only a few😍

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  2. Been here a few times, there is so much to see/do and what FUN! We’ve stayed at Ocean Key Resort each time, overlooking Mallory Square and Sunset Key for the sunsets. Our last visit was Feb 2020, when the pandemic was hitting NY, we saw George Thorogood in concert, we had a blast. What happens in Key West, stays in Key West! 🙂

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    1. What a fine place to stay at, Donna! I bet you had an amazing time🙂 This was our first international travel since the pandemic started, and we enjoyed every second of it! Coming from Canada, after excessive periods of lockdown and restrictions, we found Florida a little paradise😍

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  3. I loved Key West when we stayed there back in 1992! Your post has brought back many good memories of that visit, like the Hemingway House and sunset at Mallory Square. But it seems to have got more busy with tourists – we didn’t have to queue to take photos at the buoy and I don’t think there were all those ‘attractions’ at Mallory Square! But I’m happy to see that it’s still a fun place to visit and still has that slightly subversive vibe 🙂

    Liked by 1 person

    1. Glad to bring you back fond memories!
      I believe people are exaggerating while taking photos at the buoy, hence the long queue. I watched for few minutes a family of 3 taking photos of themselves – then we left.. they were still there🙂 But yes, Key West in general was bustling with people, I guess this happens during the high season. It was a great escape from our long winter for sure😍

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    1. Indeed, the cats are all over on the museum premises. Some of them were so bold, jumping on the table, but others so shy, turning the head away when approaching them.

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  4. I’ve never been to the Florida Keys and had a different idea of it than you showed. It looks and sounds much more relaxed and low key than I imagined. I’d love to see Hemingways polydactyl cats!! Maggie

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    1. This was only about Key West. The other ‘Keys’ definitely look different, as they are much smaller than this island. We passed by some of them driving on the Overseas Hwy back in 2015. I would love to slow travel through all of them once again, and try snorkeling- Next time🙂

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  5. I always wanted to go there, but I think the Hemingway days are long gone and it sounds a bit touristy for me. Greedy to want to keep things to yourself, but I always do. Thanks so much for taking me along with you, Christie. It’s appreciated.

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  6. I’ve never been to Key West but heard nothing but great things about it, and how can you not – it is an amazing destination you’ve got to experience, especially driving the Overseas Highway! You’ll for sure sound like a local if you pronounce Conch the correct way 😉 I am glad to see you had a great time. Thanks for sharing and have a good day 🙂 Aiva

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    1. You got it right! Overseas Hwy is an amazing drive, with so many wonderful islands along its way. A perpetual summer in those lands, what is not to love😍
      Hope you had a nice weekend! xx

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