How to spend two days in Key West, Florida

The Florida Keys are a coral cay archipelago (a chain of islands that form on top of a coral reef) that begins just south of Miami and extends in a smooth southwest arc to the southernmost point in the United States–Key West. Last December, more specifically during the New Year holiday, we were fortunate to spend two days in Key West. Advertised as a tropical paradise, the island didn’t disappoint.

The Keys is one of these places on which the journey is as fascinating as the destination itself. Our road trip started in Miami after we picked up our rental car at Miami International Airport. On a straight shot, the drive would take over three hours on the scenic 113-mile Overseas Highway. Our ride took much longer since the scenery was an invitation to slow down and take in all the beauty surrounding us

Key West Overseas Highway

Key West is small! The island measures only four miles long and about two miles wide. Yet, we were astonished to discover that despite its size, this drop of land at the end of an island chain had no shortage of fun things to do. During our two-day stay, we enjoyed beautiful beaches, stunning sunsets, and water activities just to name a few.

This itinerary is based on our own experiences. The sites and activities listed below are from among the many attractions available in the area. At the end of this post, I will list what else we would have done if time weren’t an issue. 

If you are planning to visit beautiful Key West, read on! Here you will have answers to all your questions, as well as useful information about the best attractions, where to stay, and transportation.

10 reasons to visit Key West

1. The ride from Miami to Key West

First things first: the drive! The Overseas Highway, also called “the Highway that Goes to Sea,” is a dividing line between the Atlantic Ocean to the east and the Gulf of Mexico to the west. Built mostly over the water, our views were often the extensive blue-green water on both sides of the road. However, limestone islets, coral, and mangroves bordering the roadway didn’t go unnoticed. 

The Florida Keys comprises 1,700 islands, but only 43 are connected by the highway, which includes extensive elevated bridges that connect one island to the other. The Seven Mile Bridge, the most famous on this route, is one of the world’s longest segmental bridges (bridges built in short, concrete sections). 

Morada Bay Beach Café

Driving from North to South the five well-known islands in the Florida Keys are Key Largo, Islamorada, Marathon, Big Pine Key, and finally Key West. Although there are plenty of scenic viewpoints along the highway, our first stop was in Islamorada. At Morada Bay Beach Café our vacation mode really kicked in.

Morada Bay Beach Café

Located in the heart of Islamorada at mile marker 81.6, Morada Bay Beach Café is an outdoor restaurant that honored our first stop. We were initially attracted to its location near the water and surrounded by palm trees. The outdoor tables sat in the sand and the colorful surfboards decorating the walls also caught our eyes. We had our toes in the sand while we enjoyed our meal and overlooked the Florida Bay. The restaurant not only offered a laid-back atmosphere, but also an excellent variety of fresh seafood and drinks.

2. Discover Old Town

 Old Town is the soul of the island. As we walked through its quaint, narrow streets, we witnessed the best of the island from classic Conch cottages and soaring Victorian homes to the most popular tourist attractions. Duval Street, which stretches from Mallory Square to the Southernmost Point marker, is Key West’s main tourist strip. Tourists, we included, gathered in restaurants, shops, and art galleries which created, day and night, a joyful and contagious atmosphere. 

Old Town Key West

Mallory Square, which overlooks the Gulf of Mexico, is famous for Sunset Celebration. Although we found it to be too crowded (probably due to New Year’s Holiday), a stroll through this area was essential to watch street performers, musicians, dancers, and all types of colorful entertainers. Moreover, when the Florida Keys and Key West officially became part of the United States in 1822, the first American flag was placed in Mallory Square. 

Other attractions within Old Town are Key West Lighthouse, Mile Marker 0 Sign, Hemingway House, and Fort Zachary Taylor State Park and Beach.

3. Snap a photo at the southernmost geographic point of the United States

Southernmost geographic point of the United States

Did you know that Key West is the southernmost geographic point of the 48 contiguous states in the United States? Curiously, Key West is closer to Cuba (90 miles) than to Miami (140 miles.) That said, do not miss the opportunity to take a picture in front of this renowned landmark. Depending on the time of the year you are visiting, be prepared for a long line as it is one of the most popular attractions in the city.

4. Climb up the Key West Lighthouse 

Completed in 1848, the Key West lighthouse was originally powered by 15 oil lamps that helped guide sailors to the island. Although it no longer serves as a functioning lighthouse, it is another attraction that cannot be missed. Start your visit with a stroll through the gardens, followed by a visit to the tiny museum (the former keeper’s quarters) which provides an interesting look into the history of the lighthouse. Then, climb the 88 narrow steps to the observation deck which provides 360-degree views of the city and beyond.

Key West Lighthouse

There is a fee to enter the lighthouse which includes entrance to the museum. It also includes audio and video recordings as well as glass display cases of the previous owner’s possessions.

5. See Fort Zachary Taylor Historic State Park

Designated a National Historic Landmark in 1973, this 54-acre state park is a popular site for recreation, as well as American history. Fort Zachary Taylor, built between 1845 and 1866, played important roles in the Civil War and Spanish-American War. The fort, built to defend the nation’s southeastern coastline, once held the largest collection of Civil War cannons in the United States. Some of them are still there.

Fort Zachary Taylor Historic State Park - Florida

Before heading to the beach located within the park, I highly recommend exploring the fort and take in all its rich history!  The park is also home to several nature trails.

6.  Enjoy Key West beaches

Something you can’t miss in Key West is visiting its beautiful beaches. We chose Fort Zachary Taylor Beach which is considered the most beautiful on the island. Although we had to pay a fee to get into the park, it was totally worth it. The entrance gave us access to both the ruins and the picturesque beach.

Key West beaches

Located at the south end of the park, Fort Zachary Taylor Beach is a perfect place for families. Not only were the crystal-clear water and mild currents an invitation for swimming and snorkeling, but also kiosks on the sandy beaches serve delightful food and drinks. Chairs, umbrellas, and water sports equipment are available for rent. While lying on the sand and enjoying the warm weather I had fresh coconut water bought from vendors walking by. Such experience took me back to Brazil, where I grew up. It is one of the most refreshing and healthiest drinks I have had on the beach. We spent only a couple of hours there, but we would love to have stayed the whole day. 

Check out this guide to find out about other top-rated beaches in the Florida Keys  and Key West.

7. Visit Harry S. Truman Little White House 

If you are a history lover, you must visit the Harry S. Truman Little White House. Built in 1890 to serve as command headquarters during the Spanish-American War, it also served as a naval base through World War II and the Cold War. In 1911 it was turned into a single-family residence.

Harry S. Truman Little White House

Although Truman wasn’t the first American president to visit the site, he used the building as the winter White House. He spent 175 days of his presidency there, thus the building earned its name. Nevertheless, Truman wasn’t the only renowned visitor who stepped into this site. President Taft made a stop at the Little White House on his way to inspect the progress of the Panama Canal. The scientist Edward Hayden stayed there while conducting Hurricane research, and in 1918 Thomas Edison lived in the house for six months while perfecting underwater weapons to be used during World War I. Other American presidents such as Kennedy, Eisenhower, Carter, and Clinton used this home during their presidencies either as a facility or getaway. 

 The original furnishings and decor have remained intact from the Truman era. During a guided walking through we saw Truman’s piano and the desk he used while working from Florida.

8. Eat seafood and Key Lime Pie

Located where the Atlantic Ocean and the Gulf of Mexico meet, the island overflows with seafood restaurants that offer a wide variety of flavors. From shrimp and lobster to crabs and an array of fish locally caught and deliciously prepared, I personally had difficulties choosing what to order. During our two-day stay, we dined at Thirsty Mermaid and Firefly Restaurants. Boy, oh boy! Their menus focus on fresh ingredients, and no matter what you choose, I guarantee you will be happy.

Perhaps Key West’s most famous food is key lime pie. Found in various forms, its traditional form is made with the combination of condensed milk, limes, and egg yolks. Key lime pie is literally everywhere, from street-side stands to almost every restaurant’s dessert menu. You’ll surely regret it if you don’t try this island specialty.

9. Adventure on one (or two) of the many water activities available

As far as water activities go, Key West has a lot to offer. Along with snorkeling and diving on the calmest, clearest turquoise waters, there are also parasailing, kayaking, fishing excursions, dolphin encounters, and a classic sunset cruise. In our opinion, a Florida Keys adventure wouldn’t be complete without including at least one water sport. 

Parasailing in Florida

We chose parasailing! After meeting the company on the dock, we left on a small boat with two crew members. Their dedication to providing the best parasailing experience was remarkable. They took the time to explain what will happen and how it will feel. Since they had no other way of communicating during the flight, they showed us some hand signals to use. We had confidence the experience was going to be amazing, but it was comforting to know what to do if something didn’t feel right.

Life vest and harness on, it was time to launch. A winch, which worked much like a fishing pole, lifted the chute and us from the boat and into the air without jerks, bumps, or jolts. At that point I was speechless. We soared through the air with a beautifully colored parachute above us while the crystal-clear blue water of the Gulf of Mexico lay below.

It was our first time doing parasailing and we loved it!

10. Watch the sunset

Key West is famous for its sunset, and when planning this trip to the southernmost point of the contiguous United States I spent some time searching the best spots to see this phenomenon. People swore by specific spots and I took notes on all of them. Upon our arrival on December 30th, we realized the island was crowded—no surprise. Mallory Square and Sunset Pier, the hottest spots to watch the sun dip down on the horizon, were jam-packed. Although we enjoyed the festive atmosphere with street performers, music, and tons of people, it wasn’t what we expected.

Sunset in Florida

The truth is, in Key West you can experience the sunset from pretty much anywhere, and the next day we chose a different spot: the White Street Pier. We shared the space with other families and loving couples, but the place was quiet. While sitting on the short wall segments of the promenade, we had our eyes steady on the horizon waiting for the ritual to begin. Slowly the orange ball of fire stretched its gold hues far and wide in the sky.  It was beautiful! For a short time, the sun was half in the water, but its reflection in the sea made it look complete. When it disappeared, the darkness of the sky intensified, registering the end of another day! It was the end of 2019 and we couldn’t wish for a better way to say our good-byes.

What we missed

Dry Tortugas National Park

 Almost 70 miles west of Key West lies the remote Dry Tortugas National Park. Made up of seven small islands, this 100-square mile park is mostly open water.  Accessible only by boat or seaplane, the park is famous for its picturesque blue waters, superlative coral reefs, and marine life. It is also the home of magnificent Fort Jefferson.

The Ernest Hemingway Home & Museum

 Home to Nobel Prize author Ernest Hemingway for nearly 10 years, the museum illustrates Key West’s deep literary history with its most famous literary resident. Hemingway composed several of his best-known works there.

Mile Marker 0 Sign

Although it would take us only five minutes to see the US1 mile-marker “0” sign, we sadly missed it. My husband and daughter didn’t care for it, but I thought it was an interesting curiosity on the island. Moreover, it could be a great photo op. 

The mile-marker “0” sign marks the beginning of the route that stretches for nearly 2,400 miles from Key West to Fort Kent in Maine, at the Canadian border. It is the longest north–south road in the United States. The Overseas Highway is in fact a stretch of US1 that connects South Florida to the Florida Keys.

How to get around 

The island of Key West is quite small and presents bustling traffic and many parking restrictions, especially in the historic area. Our advice is to put on a comfortable pair of shoes and leave your car at the hotel or one of the city-owned pay lots. You can also take a chance on finding metered or non-metered street parking. 

When in the historic center, there are many ways to get around Key West. Besides walking, you can rent a bike, a moped or an electric golf cart, take a taxi or a pedicab, or ride city buses, trolleys, and hotel shuttles.

Being a family of three, we chose to rent an electric golf cart for a half day. What a fun way to do a sightseeing tour! Furthermore, it maximized our time on the island. Be aware that they are subject to all traffic rules, including parking.

Where to stay

Key West’s accommodation covers two groups: beach resorts and 19th century mansions that have been turned into hotels. Both styles can be found in Old Town, which is, in my opinion, the best area to stay in Key West. This part of town boasts colorful streets, picturesque shops, museums, galleries, as well as an array of dining options and attractions, including Mallory Square, Duval Street, and Fort Zachary Taylor.

Hotel Recommendations:

Top-notch: 

 Ocean Key Resort & Spa – Located at the end of Duval street and right next to sunset pier. Offers waterfront rooms with balconies and an oceanside pool. Due to its fabulous location, it can be noisy.

Mid-Range:

La Concha Hotel & Spa – The location, right on Duval Street, makes it easy to stop by the room if needed. This historic hotel features a Tiki Bar, a small outdoor pool, a fitness center, a rooftop spa, and an exclusive wine bar.

Budget:

Fairfield Inn & Suites by Marriott Key West at The Keys Collection – Located off US-1 it is 1.1 mile from Key West International Airport and 3.2 mi from Duval Street, this hotel provides shuttle service to Old Town. Great deal for the value.

YOU MAY ALSO LIKE

Why Seaside, Florida is the best destination for your family trip

Civil Rights Movement Trail: a road trip through the Southern history

Best things to do in New Orleans

Leave a Comment