Located at the southernmost tip of the Florida Keys, Key West is a highly sought-after tourist destination. The island attracts visitors from all over the world. It can feel overcrowded at times, but the blend of history, natural beauty and vibrant atmosphere make it a good point of interest for your trip.
Part of Key West’s allure lies in its connections to iconic figures such as Ernest Hemingway and President Harry S. Truman. The city’s Old Town district is a treasure trove of well-preserved historic buildings. Wandering the streets of Old Town, you can see picturesque Victorian-era homes, vibrant conch-style houses, and an array of boutiques, art galleries, and dining establishments.
Additionally, Key West has a unique fusion of Caribbean, Cuban, and Bahamian influences. The island’s architecture, cuisine, and vibrant festivals reflect this diverse heritage. Art enthusiasts can explore galleries and studios that exhibit the works of local artists.
But, if you do not like places that are overly popular, a day in Key West might not be for you as it is difficult to avoid feeling like every person around is a tourist. Also consider that this is a place where adults enjoy exploring food and drinks, and as such it might not be a perfect spot for a family vacation.
Getting to Key West
You can get to Key West by car or plane. However, our recommendation is for you to take the drive from Miami and enjoy the Overseas Highway through the Florida Keys. The drive is about 4 hours. It will take you over 42 bridges, the most famous of which is the Seven Mile Bridge.
Prioritize What to See in Key West
Key West is a relatively small town, but it offers plenty of things to do and places to visit. Use our recommendations below as a guide and be sure to pick the activities and places that are of interest to you to make the day more manageable. Additionally, it is often very hot during the day in Key West, so allow for some downtime during lunch and in between activities to make the most of your day and keep it enjoyable.
In the Morning: Explore Old Town Key West
Old Town Key West is the historic district of the city, known for its charming streets, colorful buildings, and rich history. It is home to iconic landmarks like the Ernest Hemingway Home and Museum, where the famous writer once lived, The Little White House used by many US presidents, and the Key West Lighthouse and Keeper’s Quarters Museum, offering panoramic views of the island.
Explore Duval Street
Duval Street is the heart and soul of Key West, renowned for its vibrant and energetic atmosphere. Stretching from the Gulf of Mexico to the Atlantic Ocean, it is the main thoroughfare of the city’s historic district. Start at the Ocean Key House, located at 0 Duval Street, and walk towards the opposite end where The Southern Most House Hotel is located. Enjoy the many shops and galleries along the way, as well as the restored buildings and mansions.
Of note:
- Sloppy Joe’s Bar – open since 1933 and a favorite hangout of Earnest Hemingway.
- The first successful Jimmy Buffet’s Margaritaville restaurant, open since 1985.
- The Oldest House in Key West and all of South Florida built in 1829 and located at 322 Duval Street.
- The Key West Butterfly and Nature Conservatory – a glass-enclosed structure where you can explore birds and butterflies in an interactive setting.
Visit the Southern Most Point in the USA
The Southernmost Point in the USA is an iconic landmark located in Key West, Florida. It marks the tip of the continental United States and is a popular tourist attraction. The marker serves as a symbolic representation of the geographical extremity of the country. Visitors can take photos with the buoy, which stands just 90 miles from Cuba, and enjoy the scenic views of the ocean. Be prepared to wait in line to take your photo as this is a very popular tourist destination. Alternatively, you can get there really early in the morning and avoid the crowds.
Visit the Hemingway House
The Hemingway Home and Museum in Key West is a must-visit destination for literature enthusiasts and fans of Ernest Hemingway. It provides a captivating glimpse into the life of the iconic writer, featuring his former residence, personal belongings, and the famous polydactyl cats (i.e., cats born with more than the usual number of toes on one or more of their paws) that continue to roam the property. It’s an enriching and memorable experience that celebrates the legacy of one of America’s most well-known authors.
Be sure to take the guided tour. It is only thirty minutes, but it is very informative. Also note that tickets are cash-only and available at the gate. No reservations are required.
Stop by The Little White House
The Little White House in Key West, Florida holds historical significance as the winter White House of former President Harry S. Truman. Built in 1890 as naval officers’ housing, the house later became a retreat and vacation home for several U.S. presidents, including President Truman.
During his presidency, Truman spent a significant amount of time at the Little White House. It was his winter retreat and a place to both relax and make important decisions. Today, the house has been transformed into a museum that offers a glimpse into Truman’s private life and the important events that took place during his presidency.
Other US presidents who have used this house include William Taft, Dwight Eisenhower, and John Kennedy.
You can purchase tickets online here or at the museum.
Be sure to explore the neighborhood around The Little White House. Enjoy the many historical residencies which have been beautifully restored.
In the Afternoon: Enjoy the water around Key West
Considering that Key West is surrounded by water, there are plenty of water activities you can enjoy. Rent jet skis or kayaks and explore the ocean at your own pace. Go on a boat ride and see coral and fish, or simply spend some time at a local beach.
Take a glass bottom boat tour
A Glass Bottom Boat tour offers a unique way to explore the beautiful marine life and underwater world. As the boat glides over the shallow reefs, passengers can marvel at the colorful coral formations, tropical fish, and other fascinating sea creatures that inhabit the area. The glass bottom provides an immersive experience, offering a close-up view of the underwater environment without getting wet.
Of note is that the coral reef near Key West is the only living coral barrier reef in the continental United States. It extends approximately 150 miles from Key Biscayne in Miami to the Dry Tortugas, with Key West located right in the heart of it.
You can buy tickets and board at 0 Duval Street in front of the Ocean Key House. Book your tickets online here.
Enjoy time at the beach
Key West is home to a number of beaches that you can choose from, each offering something a little bit different. Here are some of the more popular ones:
- Smathers Beach (2601 S Roosevelt Blvd, Key West, FL 33040): Located on the southern coast of the island, this is one of the largest and most popular beaches in Key West.
- Higgs Beach (1000 Atlantic Blvd, Key West, FL 33040): Situated near the White Street Pier, Higgs Beach is a family-friendly spot with a wide sandy beach area.
- Fort Zachary Taylor State Park Beach (601 Howard England Way, Key West, FL 33040): Located within Fort Zachary Taylor Historic State Park, this beach is known for its clear turquoise waters and soft sand. It offers excellent snorkeling opportunities around the rocky formations near the water’s edge.
In our opinion, the beaches in and around Key West are not as beautiful as the beaches you will find in much of the rest of Florida. The water is a bit murky at times, there are more creatures in it, and seaweed has been a bit of a problem in recent years. We prefer exploring the waters around Key West by boat, kayak or jet ski, rather than swimming in it. And if you go in the water, definitely bring water shoes to ensure you do not step on sharp coral or water creatures.
In the Evening: Join in the sunset watching tradition of Key West
Sunset watching in Key West is a cherished tradition and popular activity among locals and tourists alike. On the western tip of the island, you can see breathtaking views of the sun as it sets over the Gulf of Mexico.
Here are some ways to join in:
- Mallory Square Sunset Celebration – one of the most iconic sunset experiences in Key West. Every evening, locals and visitors gather at Mallory Square to witness the stunning sunset. Street performers, musicians, food vendors, and artisans create a lively atmosphere as the sun dips below the horizon.
- Sunset at the Southernmost Point: Key West’s Southernmost Point, marked by a buoy, offers a unique perspective for sunset viewing.
- Sunset Pier at 0 Duval Street – one of our favorite places to grab a drink and watch the sun go beyond the horizon.
Where to eat in Key West
There is no shortage of good food options in Key West. In general, you do not need to make reservations. Here are a few of our favorites:
- Sunny Eggs – a casual French-style cafe with plenty of good breakfast options and excellent coffee.
- The Koffie House – a quirky place with a variety of tasty and healthy selections for breakfast or lunch. You can also pick items for a nice picnic.
- El Meson De Pepe’s Restaurant & Bar – Cuban food, live music, excellent drinks and sunset views.
- Nine One Five – for a special dinner and more sophisticated experience. This bistro and accompanying bar is located in a magnificent Victorian house built in 1850.
- The Bull and Whistle Bar – classic open-air bar with live music. Try their Service 2 for 1 Margaritas or other daily specials.
- Kermit’s Key West Key Lime Shoppe – enjoy key lime pie by the slice or pick one of many other lime treats made locally.
- Mattheessen’s Candy Kitchen – cookies, ice cream and fudge. 😋
What we loved about Key West
- Unique and quirky town where you can enjoy a slower pace of life
- A place with interesting and well-preserved history
- Good food with plenty of Carribean influences
- A good variety of things to do – history, nature, nightlife
- Spectacular sunsets and a chance to participate in a longtime ritual – sunset watching, enjoyed daily by locals and tourists alike
- Key lime everything – pies, soaps, cosmetics, spices and more
What to bring
- Plenty of sunscreen. We like this one, this one and this one.
- A good hat of your choice
- Sun protective clothing as you can expect to be in the sun quite a bit. Also, light and breathable clothing.
- Sunglasses. Right now, we love this and this pair.
- Comfortable shoes as you will do a lot of walking
Check out our list of travel essentials on what to take and how to maximize your packing.
In closing, a trip to Key West, the southernmost point of the United States, should definitely be on your travel list. Its unique setting, history, culture and atmosphere should be experienced at least once.
Additional resources and inspirations
Here are some links to additional resources you might find useful and inspirational for your trip to Key West, Florida:
by WorldWide Travel
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