Key West Attractions

The highlight of a drive on the Overseas Highway in the Florida Keys is a visit to Key West, the largest city at the end of the islands. Here, at the southernmost point of the Florida Keys chain, everything is different.

Key West has famous attractions like Mallory Square, the hustle and bustle of Duval Street, or the Hemingway House. However, if you turn down one of the side streets, you feel like time has stood still among the pastel wooden houses. Everyone greets everyone, and the rhythm adapts to the Caribbean heat: slow and relaxed.

Key West is polarizing. Some people love Key West and keep coming back. Others visit the place only as part of a day trip from Miami through Key Largo and Big Pine Key and the famous Seven Mile Bridge. Overall, you pass by 42 bridges during the drive. I loved Key West with all my heart and enjoyed walking or riding my beach cruiser bike through the streets.

In this article, you will find my Key West highlights (with sights and additional tips). Things you absolutely should do!

Enjoy reading!

In Key West, there are many activities and good reasons not to be lazy:

In Key West, I enjoyed exploring the streets either on foot or by bike. Sometimes with a clear destination in mind, or completely aimlessly just wandering around.

Out of laziness, I also took a short ride on the Conch Tour Train during the midday heat and listened to what the driver had to say about some places. Here are my personal highlights in Key West:

In the historic district, the many pastel wooden houses are the main attraction. I found it hard to choose a selection of pictures, as I took at least 50 more photos of the various houses. For me, it is one of the top attractions in Key West.

In the historic district of Key West, I felt like I was in an oasis with green gardens, small galleries, and restaurants. The most famous of the wooden houses is probably the home of the writer Ernest Hemingway.

Here's a small selection of the pastel wooden houses in Key West:

On my "things I must do" list were two things. Snorkeling at the world's 3rd largest coral reef and going on a sunset cruise. Both are great highlights in Key West.

Sebago's offer sounded fitting. A catamaran tour for snorkeling at the coral reef followed by a return ride with a stop at sunset on the sea.

The sunset cruise was fantastic, and I highly recommend it. First, we received a brief orientation, then we set off. Out of the harbor and on a roughly 1-hour journey out to the open sea, occasionally accompanied by dolphins.

It was great to see Key West and the promenade with Fort Zachary Taylor Historic State Park from the water. A completely different view of the islands.

After that, we could dive at the reef for a while. Twice, reef sharks suddenly appeared out of nowhere in front of us. I was so startled because the underwater visibility was quite good and clear. But just as quickly as the sharks appeared, they were gone again.

On board, you also get cool drinks. At sunset, there are champagne or beer, as much as you want.

The sunset was beautiful and kitschy. You could see the hustle of Mallory Square from afar and did not regret rocking on the sea.

As an alternative to the catamaran, you can take a similar tour with a real sailboat. Since we booked spontaneously in the morning, this tour was already fully booked:

The writer Ernest Hemingway lived in Key West on the Florida Keys from 1931 to 1940. You can visit his estate today, as well as the descendants of his famous six-toed cats, who lounge around the house and garden enjoying the many strokes from numerous visitors.

Hemingway bought this house for only $8,000, a bargain. Today, you'd probably have to add at least two zeros. The most popular attraction in Key West is definitely this house.

It is said that Hemingway was inspired here in Key West to write his work 'The Old Man and the Sea'. Original title: The Old Man and the Sea - I had to read it in high school. For this masterpiece, he received the Nobel Prize for Literature in 1954.

Directly across from the Hemingway House stands the next attraction: the Key West Lighthouse. I also visited the Key West Lighthouse Museum to catch the view over Key West. As a visitor, you have to climb 88 stairs to stand at the top.

From the top, you get a great view of Key West and the harbor, where cruise ships anchor, much taller than any building in Key West.

The lighthouse was built in 1847 and replaced a wooden lighthouse at Whitehead Point that was destroyed by a hurricane. You can also visit the Light Keepers Quarter - the houses where the keepers lived with their families.

This place can be described in one word: crazy!! Mallory Square is where mostly all the people in Key West gather before sunset. Particularly American tourists flock to the spot where the sunset over the Gulf of Mexico is not only admired but also applauded and celebrated. Yes, you heard right, it's applauded. Everything is different here. For me, it is the most extraordinary highlight and happening in Key West.

Mallory Square is not just a square; it's also a promenade that is packed at dusk. Together with a former colleague who was also visiting, we couldn't miss this spectacle. It couldn't be more American. You have to see it.

All the performers and freaks that hang out here are incredibly ... crazy. One wants to predict the end of the world for me. Another rambles on about Jesus. A fortune teller wants to foresee my future. Others put on fire-breathing shows or juggle. Some have trained monkeys. The latter I abhor, and we gave that a wide berth.

An older man casually mixes mojitos, children line up at ice-cream stands. The sea is dotted with boats and catamarans from sunset cruises.

This all sounds touristy, and it is exactly that. Still, you must visit this spectacle once. Afterward, everyone heads to one of the many restaurants or bars.

That's how you spend an evening in Key West, Florida.

The southernmost point of the continental United States (excluding Hawaii) is located at the edge of Key West. It is probably the most photographed symbol in all of Florida. Many tourists crowd around the cement buoy, standing in line to get a photo with the Southernmost Point of the USA.

By the way, Cuba is only 145 km away from here. This attraction markets itself well. Because as we passed by on our bikes, we saw the Southernmost Hotel, the Southernmost Guesthouse, Southernmost Beach, and the Southernmost Restaurant.

Travel tip: Be sure to bring something to drink and a head covering in case you have to wait in line. There's no shady spot, and the sun is shining down pretty hard.

The most famous street in Key West is Duval Street. Most tourists gather in bars, souvenir shops, or stylish restaurants with inviting porches (which I think are completely overpriced). Everything here is a bit crazier than anywhere else.

You can't avoid this street if you want to get from A to B. Even if we walked new paths and used parallel streets, you pass by Duval Street at least once a day.

One evening we spent at a very stylish restaurant whose porch was set back from the street. From here, you could relax and watch the bustle with delicious food and a nice glass of wine. Unfortunately, the restaurant itself was quite expensive.

For me, the best way to explore Key West is by beach cruiser. Even in the heat, you get a fresh breeze now and then and navigate much more "around" than on foot. During our visit, there were hardly any cars, making biking very relaxed.

Experience an unparalleled journey through time when you visit Fort Zachary Taylor State Park in the southwest of Key West. The former military fortress, which provided protection on the southern coast of America from 1845 to 1947, features original artifacts and weapon collections to discover the rich military history of the United States during a visit.

Then head into the park and learn about the diverse flora and fauna. From majestic native trees to migratory birds seeking refuge here - there is something for everyone! If you're looking for peace, you can choose between the sandy beach and the coral reefs with their colorful underwater world.

If you're feeling lazy and the heat is getting to you, buy a ticket and get on the Conch Tour Train. The train is one of the most popular attractions in Key West and is always well-visited. It stops at over 20 attractions in Key West.

We succumbed to the temptation of using the tourist train for a few minutes. We could listen to stories and historical information on the sightseeing tour with the Conch Train. Shady seat included.

A tour with the Conch Tour Train lasts 1.5 hours. You can get on and off at any stop. The ticket is valid all day and costs about $30.

For more information about the stops, visit the official website.

The Harry S. Truman Little White House was the headquarters of the Marine command during the Spanish-American War from 1890. It served the same function in both World Wars. In 1946, the building became the Winter White House of President Harry S. Truman. Later presidents used it as a place of peace and relaxation, especially in tense situations like the Cold War.

While the house is still used by the heads of state as a retreat, it is also a publicly accessible museum. The official protocols of trips and visitors in the museum are interesting documents to view.

During tours, you can learn much more about Harry S. Truman's presidency, the era of the Cold War, and the naval history of Key West.

For history buffs, a visit to Dry Tortugas National Park with its spectacular 19th-century Fort Jefferson is a must. The park, which consists mainly of water and seven small islands, is located about 70 miles (approximately 113 km) from Key West. It is situated in wonderfully turquoise waters surrounded by a variety of colorful coral reefs and diverse marine life (including turtles). There's also a large colony of migratory and tropical birds.

You can reach the island by boat, ferry, or seaplane. On-site, there are 45-minute guided tours through the fort to learn more about the history. Snorkeling and swimming are allowed in designated areas.

You can book a tour directly via Viator. The package included a catamaran ride, a guided tour through Fort Jefferson, and swimming or snorkeling at the park's coral reef with dolphins and sea turtles.

In Key West, by the way, the Highway Number 1 (Overseas Highway) begins and ends and at the same time the Florida Keys Scenic Highway. Look for the sign to take a picture.

The following map gives you an overview of the attractions in Key West. You can also download the city map with all the attractions, places of interest, and tips for food, bars, and other highlights to your phone and navigate quickly and easily through the city:

In Key West, there is mainly one thing: expensive restaurants. Even a slice of pizza in a side street off Duval Street costs at least $7 (and wasn't even that good). You absolutely should try a Key Lime Pie, the specialty of the Florida Keys (and simply delicious).

Therefore, here are my tips for restaurants and cafes where we had a really good meal and partially inexpensive (for Key West standards):

At Fisherman's Cafe, you must stop by when you're in Key West. You will find the cafe right at the meeting point in the harbor for the sunset cruises. Therefore, it's the ideal spot to grab a sandwich and sweet potato fries to go before departure. Refreshing iced coffee was served as well.

At La Creperie, we dined divinely! The breakfast wasn't cheap, as we ordered fresh-pressed juices in addition to crêpes and coffee. Still, it's worth eating here. The portions are generous and lasted until the evening.

If you're not into the American version of pizza like I am and prefer the real Italian kind, you must visit Duetto Pizza and Gelato. Best to visit on the way back in the evening from Mallory Square. I not only had pizza but also ice cream for dessert. Recommended, and many locals enjoy their meals here away from the hustle.

Haven't you driven through the Florida Keys like we did and already tried Key Lime Pie? Then you must try these delicious pies at the Key Lime Factory. The specialty of the Florida Keys is too good to only taste once.

The pie has been voted "Best in Florida" several times in a row by Florida Monthly Magazine. Not into lime? You can also order frozen Key Lime Pie on a stick (like ice cream), Key Lime Pie cookies, Key Lime candies, and Key Lime Rum cakes.

First the bad news: Cheap accommodations - whether a hotel or Airbnb - do not exist in Key West. I certainly couldn't find any. Therefore, we found a room on Airbnb in a beautifully pastel yellow house. The location on a parallel street to the central Duval Street was great.

Unfortunately, our Airbnb accommodation is no longer available online.

LOOKING FOR A HOTEL?

For finding a good hotel, we recommend the platform Booking.com. We always book our accommodations on this platform or directly with American Express, as we gain additional discounts with the American Express Platinum Card (see details, only worth it for frequent travelers).

In Key West, many dropouts and former hippies live who attempted to declare independence in 1982 as the 'Conch Republic'. The name originates from the local fighting conch, a pink-hued shell. Everything here is more laid-back, relaxed, and not as strict as in other parts of the USA.

You can explore the main attractions in Key West in one day. However, you should plan to stay for at least 2 to 3 days if you want to take trips (boat tours, snorkeling).

Having undertaken a road trip through Florida, I was looking to uncover tips and also visited Miami, making the selection for a good travel guide not easy.

I can recommend these:

Key West is the largest city of the Florida Keys and is located at the end of the island chain in southwestern Florida. From Miami, the best way to get there is by bus over Highway 1 from Miami to the destination. Alternatively, you can take the ferry from Marco Island or Fort Myers. We did a road trip in Florida by car and drove to Key West on our own. The advantage is that you can also visit all the beautiful places of the Florida Keys between Miami and Key West.

Florida and Key West can be visited year-round. It is always warm, and the sun shines almost every day. However, you should note that from May to October is officially the rainy season. These are the least popular (but cheapest) months for a Florida trip. It usually only rains briefly but heavily. The only downside is that it is very humid.

I visited in May and found it great. It hardly ever rained; it was just extremely humid on the Florida Keys and Key West.

The main travel season is our winter between December and April. Many retirees are also in their vacation homes in Florida at that time, making it crowded. Prices in the Keys are generally extremely high, but the temperatures during these months are very pleasant.

From August to October is hurricane season. However, that shouldn't stop you from traveling to the USA. It can always happen that a hurricane disrupts your travel plans, even in November.

Check out my detailed experience report on the best time to visit Florida.

In Key West, just like in general in the United States: Look for one of the numerous coupon books and check for discounts. Here you can save valuable money for other activities, whether for a key lime pie, boat tours, or other trips.

Conclusion: Key West is always worth a visit. The place is so special that you simply have to visit it!

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In Key West, we were supported by The Florida Key and Key West with a VIP Press Pass to test many offers. Our accommodation was self-paid.