Key West in 3 Days: a guidebook for getting the most out of your visit

Enjoy everything Key West has to offer in just a few days. The idea is to get to know its historical sites, but also the natural spaces that are so attractive on this island.

Ana Caballero

Ana Caballero

10 min read

Key West in 3 Days: a guidebook for getting the most out of your visit

Chad Sparkes | ©Amanecer de Key West

Key West is an island of the Florida archipelago, with an area that seems small, but inside it holds a vast natural wealth. In addition, due to its location and beauty, it has also become a place full of history and culture. Not in vain was it chosen by several historical figures as a place to stay.

Your 3-day visit may seem more than enough, but believe me you will want to multiply the time to take advantage of the best things to do in Key West. I suggest an itinerary in which you will first go into the central area to learn about its cultural and historical value. Next, you will choose a marine experience of water sports or dolphin watching and travel to the Dry Tortugas National Park. I'll tell you more about this guide for your trip.

Day 1: Tour of Key West's historical and cultural sites

Key West Lighthouse| ©Kirby Collins
Key West Lighthouse| ©Kirby Collins

On your first day in the city, the best thing to do is to go deep into the city to see its most emblematic areas. I'm referring to the Southernmost Point of the Continental United States, the Ernest Hemingway House, the Key West Lighthouse, the Truman Little White House and the city's Aquarium.

Southernmost point in the Continental United States

At 1400 Whitehead St, you will find the southernmost point of the Continental United States, this is a very important monument for its geographic value, so taking a picture at this latitude is almost mandatory. Upon arrival, you will see several tourists doing the same and you will also have an exceptional view of the Atlantic Ocean.

From this place, which is just 90 miles from the island of Cuba, you can continue your journey to the next destination. As it is an open space with 24-hour access, you can visit it at any other time of the day, if you wish. It is not for nothing that it is always one of the stops for those who take bike tours in Key West.

Book a bike tour

Key West Lighthouse

About a 7-minute walk down Whitehead Street will take you to the Key West Lighthouse, a structure established in approximately 1825 that offers a great 360-degree view at about 19 meters high, from where you can observe other tourist and historical sites in the city.

This place is not only an observation point of the beauty of the city, but it also holds samples of history to explore. For example, you can enter the lighthouse keeper's house, which currently serves as a museum. In it, old documents such as some nautical charts are exhibited, as well as copies of newspapers from decades ago. This way, you can learn a little about the city a century ago.

Ernest Hemingway's House

Continuing on the same street as the previous destination, it will be enough to walk for about 9 minutes to reach the Ernest Hemingway House. This cozy structure has become a place of worship for lovers of the writer. It has a Spanish colonial style, quite common on the island and dates back to 1851.

The house was the writer's home since 1931 and today we can consider it a museum. In it you will see an infinite variety of decorations of the time, such as wooden furniture, fishing tools that Ernest Hemingway used for recreation and antique ceiling fans.

  • Price: about 17€ per person.
  • Hours: 9:00 a.m. to 5:00 p.m.

Truman's Little White House

If you walk for 15 minutes down the same street, heading towards Southard Street and then Emma Street and Front Street, you will arrive at Truman's Little White House. This is another place of great historical and cultural value, since Harry S. Truman, the 33rd president of the United States, lived there.

This enclosure, which can also be classified as a kind of museum, will allow you to learn about the life of former President Truman and, in a way, travel back in time. When you buy tickets for the Truman Little White House in Key West you will have access to a space full of antiques from the 1950s. You will see various objects such as furniture and the former president's personal diary. This is one of the must-see stops in the city, so you should add it to your itinerary even if your visit is less than 2 days in Key West.

  • Price: the entrance fee is from 26€ per person approximately.
  • Hours: 9:00 a.m. to 4:30 p.m.

Buy tickets for Truman's Little White House

Key West Aquarium

Now you must walk in the direction of Whitehead Street for about 4 minutes to reach the Key West Aquarium. This wonderful place is home to many marine species that will seduce everyone. Therefore, this option is ideal if you are traveling to Key West with children. This is an unforgettable playful experience to live with family or friends.

If you buy tickets for the Key West Aquarium you will be able to see exotic species such as sea turtles, hermit crabs, flathead sharks, angelsharks, etc. In addition, there is a touch tank in the aquarium that will allow you to interact with animals such as snakes, snails, sea urchins, starfish and crabs.

  • Price: the cost is usually from 21 € per person.
  • Hours: daily from 9:00 am to 6:00 pm.

Book tickets for the Key West Aquarium

Appreciate the sunset from Mallory Square

To end your first day's itinerary, I suggest you watch the sunset from Mallory Square, one of the spots in the city known for its beautiful sunsets. Once you leave the actuary behind, you will have to walk in the direction of Wall Street, for 4 minutes and you will arrive at this observation point.

Keep in mind that, according to the time of the year you visit the city, the sun will set a little earlier or later, respectively. In case you still want to continue exploring, you can head towards Duval Street, a street full of stores and restaurants where you can have dinner and do some shopping.

Day 2: Water activities and ghost tour or dolphin watching, Sails to Rails Museum and sunset cruise

Key West Beach| ©Teknorat
Key West Beach| ©Teknorat

On your second day in Key West, I suggest two options. The first is to go into the ocean for water activities and take a ghost and tombstone tour by streetcar at night. The second option is to join a dolphin watching experience and go to the Sails to Rails Museum and take a sunset cruise.

Option 1: Water Activities and Ghost Tour

To live this experience, you will have to get an adventure and water sports pass in Key West. You will head to the port to board the state-of-the-art catamaran that will take you on this experience.

You will start the day tasting a continental style breakfast while sailing and enjoying the first rays of the morning sun. The first water activity will be snorkeling, so the boat will head towards a wonderful coral reef, so you can swim with the fish and learn about the marine life that inhabits the area. Of course, you will receive the necessary guidance and accompaniment from a professional instructor.

At the end of this experience it is time to go to Fury's Ultimate Adventure, a huge aquatic complex with various activities for individual and family fun, ideal if you travel to Key West in January or any other month of the year. At noon, you can have lunch to replenish your energy and continue with the activities.

Next among the options is a paragliding experience over the ocean waters. You can also take a ride on a jet ski or go on a banana boat. You can also play in the climbing tower, participate in an obstacle course over the sea, climb on slides and trampolines, etc.

When the adventure ends at this point, it's time to return to Key West while you sunbathe from the boat and enjoy a refreshing drink that can be beer, wine or water.

Buy an adventure and water sports pass

Ghosts and tombstones trolley tour

Upon arrival in the city, you can simply take a break at your hotel while you wait to join a ghost and tombstone streetcar tour. This spooky adventure is one of Key West 's favorite nighttime things to do in Key West.

You'll hear stories about the town's dark past as you explore its alleys, old wooden houses and more. All this in the company of a professional guide. Plus, on this tour you'll enter the Key West Shipwreck Treasure Museum, one of the city's quirky places, which will take you on a journey back to the 17th century.

Book a ghost tour

Option 2: Dolphin Watching, Sails to Rails Museum and Sunset Cruise

If you choose the second option, you will live a mind-blowing dolphin watching experience. To do so, you will board a boat to enter the waters surrounding the island. The idea is that you can observe these cetacean mammals in their natural habitat and live a very special moment.

On the way to the observation point, you will be able to consume drinks to cool off from the heat. To your surprise, in fact, in this getaway you can both watch these marine animals and dive into the sea to snorkel and observe the species of fish that live there.

You will get down to work and put on your snorkeling equipment following the instructions of a professional guide. Then, you just have to dive into the turquoise waters and start enjoying the view of the ocean.

If all goes well, you will interact with bottlenose dolphins and their future prey (many of the little fish that will approach). Once the snorkeling experience is over, you will return to the boat to hydrate and enjoy an alcoholic beverage such as wine or beer, or a non-alcoholic beverage.

Book the dolphin watching tour

Visit the Sails to Rails Museum

Since you will be back with time to continue exploring the city, I suggest you visit the Sails to Rails Museum in Key West. In this place you will see distinctive elements of the era of navigation and how the evolution to the arrival of the railroad took place. You will see antique objects and other items of historical value such as a silver bar from the Spanish galleon Nuestra Señora de Atocha, which was shipwrecked in 1622.

  • Price: the entrance fee is from 14€ per person.
  • Hours: 9:30 a.m. to 4:30 p.m.

Buy tickets for the Sails to Rails Museum

Take part in a sunset cruise

To conclude this day's itinerary, I recommend that you sign up for a sunset boat ride around Key West. On this tour you will be able to appreciate how the sun bids farewell to the city with its orange and reddish tones, being an excellent opportunity to take pictures and at the same time to relax.

Day 3: Dry Tortugas National Park and Key West pub crawl

Key West pub crawl| ©John Beagle
Key West pub crawl| ©John Beagle

On the last day of your Key West itinerary, the invitation is to take a trip to the Dry Tortugas National Park. To get to this small paradise you will have to travel by ferry for approximately 2 hours and 15 minutes. You will board the Yankee Freedom III, the exclusive transport that makes transfers to the park, with a 2012 structure, which gives it a modern look and explains its speed and the safety it provides.

If you are in Key West in February or in any other month of the year, it will always be a good time to visit this small island. Its main attraction and nucleus is Fort Jefferson, with an extension that almost occupies the entire island. This enclosure dating from 1846 was never completed, but it made the region very important from a naval point of view and was used as a prison during the Civil War.

On the tour you will explore the whole place and observe the heavy weapons used by the soldiers, the cells where the accused of the assassination of Abraham Lincoln were imprisoned, the pellet furnace and the casemates from where the cannons were mounted. You will also see a boat used by Cuban migrants, called the Cuban chug, and hear stories of what life was like in the decades around 1860.

Dive and discover the marine world

After exploring the mainland area, it's time to dive to discover the extensive marine life hidden beneath this imposing structure. You won't have to go far to observe the rich ecosystem of this park. If you dive in the southern beach, you will see coral reefs and, if you are lucky, even some turtles.

On the other hand, if you dive the north beach, you may encounter a school of fish along the way that will swim alongside you. You can also explore the wrecks of other ships that wrecked in the surroundings. You will also see some shells, algae and fish species. In short, you will have a good sample of the marine habitat of the area.

Key West Pub Tour

You will return to the city with plenty of time to explore its nightlife on a Key West pub c rawl. You can do this activity on your own or with a guide. In either case, be prepared for alcoholic beverages and dress comfortably, as it may be necessary to walk for several minutes. On your tour, you can go to:

  • Sloppy Joe's, a bar that dates back to 1937 and was frequently visited by Ernest Hemingway himself.
  • The Green Parrot, another of Key West's best-known and award-winning bars, where you can listen to live music.
  • Captain Tony's Saloon, with decades of history, which hosted the leader of Cuban independence, José Martí.
  • The Rum Bar, a place made for rum lovers, with several options to choose from and taste.

Book a pub crawl in Key West

Tourist train to travel long distances in Key West

Key West Tourist Tramway| ©Wendy Berry
Key West Tourist Tramway| ©Wendy Berry

If you want to make even more of your time in Key West, one option you can opt for is the Conch Train of Key West, a fun means of transportation in which you can visit between 1 and 2 days most of the tourist attractions in the area.

Among the advantages of getting on this tourist train is the fact that you do not have to worry about how to get around Key West, because with it you can go to the attractions that are farther away from the center of the city without any problems. Sights to visit include the Sails to Rails Museum, the Key West Aquarium, Harry Truman's White House, Mallory Square and much more.

Book a ticket for the sightseeing train

Key West 3-Day Activity Highlights

  • Day 1
  • Southernmost Point, Ernest Hemingway's House, Truman's Little White House
  • Ernest Hemingway's House
  • From 17€ per person
  • From 9:00 a.m. to 5:00 p.m.
  • Day 2
  • Water activities and ghost tour
  • Fury's Ultimate Adventure
  • From 197€ per person
  • From 9:00 a.m. to 5:00 p.m. (daily)
  • Day 3
  • Dry Tortugas National Park & Pub Tour
  • Dry Tortugas National Park
  • From 220€ per person
  • From 7:00 a.m. to 5:15 p.m.