Road Trip to the Most Southern Point: Part 2 Key West, Mallory Square and Duvall Street

Key West: Tropical Atmosphere and Tropical Heat at the Southernmost Point

Key West is a very crazy island at the very southern end of Florida. You very clearly leave the subtropical area and reach the tropical climate: it is hot, very hot with a high humidity. We were there in October, not even the hottest period of the year.

The island has a very Cuban flair; you are really very close to Cuba, not only geographically. Its residents speak a different version of English, the coffee tastes more intense, somehow more Cuban and the atmosphere is unique. Life is different here, that becomes clear when you consider that these islands have indeed declared their independence from the US once. In 1982, the issue of border controls in the Upper Keys kept everyone busy and emotional. That is why the keys formed an independent state (Conch Republic) but only for a day.

The most southern point of the US (for some reason called the Southernmost Point) is here. They used to have a sign about this, but the sign got stolen too many times. Now they have a buoy. We walked all the way there and definitely underestimated the tropical heat. It was exhausting to walk at all. On the way to the buoy, you find many “southernmost”, like the southernmost hairdresser, café, supermarket, anything. In fact, there is an even more southern point but that is in the restricted military area further west. You can visit the buoy, do the walking tour, but to us it was a bit of “ok, we were there”.

Key West Downtown: Mallory Square, Duval Street, Sloppy Joes and Hemingway House

A not so nice way to put it is: Key West is a small, overly crowded, overly hot island. A nice way to say it is: it’s an island with its own attitude, strong Cuban influence but also big independence, strong temperament and everything a bit too crazy.

The two most important places in Key West are Mallory Square and Duvall Street. Mallory Square is always full of people; in the evenings the walls get crowded by people who sit there to watch the sunset. As soon as the midday heat leaves, street artists appear. There are little performances but also, art exhibits of sculptures and paintings. Mallory Square is in the northeast of the island. Tourist like to book boat tours for the sunset, you can see many boats right in front of the coast.

This is also where the most famous street of Key West starts: Duvall Street. Duvall Street is almost 2 km long, crosses the entire island and reaches from the Gulf of Mexico to the Atlantic. In Duvall Street various influences mix: Cuban, Bahamian and Victorian. There are many beautiful buildings. Two very well-known people were very fond of Key West: Ernest Hemingway and Harry Truman. Hemingway even stayed several years. The Hemingway House is in the old part of the city and can be visited. It’s only one block from Duvall Street at the southern end of the road. Its six-toed cats are a special feature, all of the descendant of Hemingway’s cat.

Ernest Hemingway Home and Museum
907 Whitehead Street
Key West, FL 33040

http://www.hemingwayhome.com
Tours are 14 Dollar per Person

Key West has become a common stop for cruise ships. You should try to get information about their schedules and when there are too many of them around. I can totally imagine how the town gets overly crowded then. There was no cruise ship there when we were there, but the island was already crowded. Definitely choose a good date to come here.
Key West is a place where many runaway teenagers go to. It seems to be a kind of challenge to make it up until here.

The most popular bar in Key West is Sloppy Joes from 1933. After moving Sloppy Joes is now close to northern part of Duvall Street.

A very special feature is the Dry Tortugas National Park, which is a bit more than 100 km from Key West and can only be reached by ferry or plane. The ferry takes 2 ¼ hours (single ride). Dry Tortugas is a diving and snorkeling paradise. If you want to go here, you need to plan an entire day to do so. We did not have the time, but I definitely want to do that one day. I’m sure it’s a huge highlight.

https://www.nps.gov/drto/index.htm

https://www.drytortugas.com/

Shuttle Busses from the Hotels

We did stay in a hotel at the eastern end of the island. All the major tourist attractions are at the western part of the island. It does not appear to be far, when you check the map, you think this is easily doable. But that’s not really the case. It’s very tropical and very hot. Every step becomes more exhausting. Several hotels offered a shuttle bus to the city center together. I would definitely use that shuttle and let them take me to the center as close as possible. We walked; it was too much, definitely! Don’t take your own car, leave it at the hotel. There is no parking and no space in general in the center.

Route and Duration

From Miami to Key West, it’s 266 km. You need 4 hours for this. The road along the keys and their bridges is outstanding. You hop from island to bridge to island and can enjoy a view over the vastness of the ocean almost everywhere. It’s a very nice route; you should have time to enjoy it. There is no point in speeding to reach as fast as possible. One thing is definitely the case: it’s the way that counts. Bring enough time to stop at various points.
Our travel agency recommended two nights in Key West. At first, I was thinking that is too much. But now, I definitely agree. Like this, you have an entire day to drive from Miami to Key West. You have many nice spots to stop: the Everglades (Flamingo Visitor Center or Ernest F. Coe Visitor Center), Key Largo and John Pennekamp Nationalpark.

You continue your route along all the Keys till Key West. There are many options to stop. You should definitely do the 7-Mile-Bridge and Bahia Honda State Park. You can easily spend an entire day like this. In the evening, you can watch the sunset from Mallory Square. You then spend a full day in Key West (Duvall Street, Southernmost Point, Hemingway House, etc.). On the third day, you drive back to the main land. Depending on what you are interested in, you can spend the morning in Key West or go back to the mainland directly and stop several times. You can for example visit everything you missed on the way to Key West or everything you liked very much.

It’s always an option to book an additional night in Key Largo or the Everglades. I think you don’t really need it when you have two nights in Key West. One night in Key West is not enough, doable if you really, really don’t have more time and leave Key West in the afternoon/evening. But two nights is definitely much better!

I would absolutely recommend that tour to Key West. It’s a very nice route, but you need 3 days (2 days) to do it. If you don’t have that, I would not do it at all.

This is Part 2 Road Trip to the Most Southern Point: Key West, Mallory Square and Duvall Street.

Part 1 of the article can be found here:

Road trip to the Most Southern Point in the US: Part 1 On the Way to Key West

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