Key West – Island Paradise

Updated 01/16/2024

Located at the southernmost point of the continental United States, Key West is usually considered the terminus of the Florida Keys, a series of islands that stretch over 100 miles beginning south of Miami at Key Largo. This tropical paradise has a unique vibe and one that is completely different from the rest of the Sunshine State. With its perpetual sunshine, beaches, boating, fishing, history, and nightlife, there is something for everyone in this eclectic town.

TIP: Key West can get very busy during some parts of the year. The best time to go to avoid crowds but still enjoy nice weather is from March to May. You can also usually find lower rates and fewer people from September to November, but that is also hurricane season. So, you may want to consider that fact when you are planning your trip. Find more information on when to visit here. 

Getting There

• Flying – If you are traveling from out of the state, it is a fairly long drive to Key West, so you may want to consider flying. Although Key West International Airport is a small airport with only 6 gates, several major airlines fly to Key West from many locations in the eastern United States. The airport is located only minutes from the center of town. Rental cars, cabs, ride sharing services such as Lyft, and public transit are all available in Key West.

• Driving – If you have the time and have never visited the Florida Keys, then driving on the Overseas Highway (Highway 1) from Key Largo to Key West is time well spent. The drive will take about 2.5 hours without stops. However, there are many interesting places to stop along the way, including

o John Pennekamp Coral Reef State Park in Key Largo
o Lignumvitae Key Botanical State Park and Indian Key Historic State Park in Islamorada
o Bahia Honda State Park on Bahia Honda Key
o Turtle Hospital and Dolphin Research Center in Marathon
o Seven Mile Bridge, one of the longest in the world, that allows you to travel nearly 7 miles over the beautiful, turquoise waters of the Florida Straights!

With so many things to see, you just may want to spend most of the day on the drive!

During the drive, be on the lookout for the Key Deer that live throughout the Keys. These little guys are tiny compared to their mainland cousins, reaching heights of only 25 to 30 inches. They are known to swim between the islands and they really do not have much fear of humans. Keep in mind they are an endangered species. So, enjoy them from a distance and definitely do not feed or approach them.

TIP: The Florida Keys do not really end in Key West, that’s just as far as you can drive. The Keys actually extend well past Key West to the Dry Tortugas. We will talk more about the Dry Tortugas, when we review Things to Do (below).

Accommodations and Dining

There are so many options for places to stay that the list would be too long to cover them all. Hotels, Inns, B&B’s, Airbnb, and private rentals are all well represented. However, the last time we were in Key West we stayed at the Southernmost Beach Resort.

The Southernmost Beach Resort  is located near the south end of Duval Street (the major street in Key West) and is only steps away from the Southernmost Point. There are a wide variety of rooms available, but our favorite spot is the second floor of Building C, overlooking the West Lawn. These rooms face southwest toward the water and provide beautiful sunset views. In fact, the cover photo for this blog post of the ship sailing in front of the setting sun was taken from the balcony of our room.

There are tons of dining options ranging from super casual to very upscale. But whatever you choose, be sure to try some of the amazing fresh seafood and imaginative drinks offered at many of the local restaurants. If you visit during Stone Crab Season (mid-October to mid-May), be sure to seek out a restaurant that has them! Served hot or cold, if you like crab, there is nothing better than fresh stone crab claws. And the best part is that stone crab claws are uniquely sustainable, since stone crabs are able to regrow their claws and only one claw can be taken at a time.

Things to Do

• Dry Tortugas – Dry Tortugas National Park is located about 70 miles west of Key West in the Gulf of Mexico. It is home to Fort Jefferson, a massive fortress that is the largest masonry structure in the Western Hemisphere and is constructed of more than 16 million bricks. The fort was used as a prison during the Civil War. Its most famous prisoner was Dr. Samuel Mudd, who was charged with conspiracy in the assassination of President Abraham Lincoln. He later received a presidential pardon for his role in saving lives during an outbreak of Yellow Fever at the fort.

The fort is an awesome place to explore and walking around the fort on its barrier walls is much like walking on a sidewalk in the middle of the ocean.

There are two ways to reach the Dry Tortugas, either by ferry or sea plane. Each has its advantages and disadvantages, but both offer snorkeling at the fort.

o Ferry – The Yankee Freedom III  ferry departs daily from Key West and takes just over 2 hours to arrive at the Dry Tortugas. You will spend about 4 hours at the fort, which will include a tour, lunch and snorkeling equipment. Plan for a full day, as you will return to Key West around 5 pm. Rates and other information are available on their web page, but the cost is approximately $220 per adult.

o Seaplane – For a unique experience try Seaplane Adventures  which leaves from the Key West airport. It will cost about twice as much as the ferry, but has some significant advantages. We took the morning flight, which means as we departed, we could see the ferry just leaving Key West. Since the flight only takes about 40 minutes, versus over 2 hours for the ferry, it means you have the fort all to yourself when you arrive.

The flight is incredible as you fly low over remote islands and ship wrecks, while the pilot narrates the entire trip. And, if you have never landed or taken off on the water, the seaplane experience is amazing!

• Snorkeling – You can use your own gear and snorkel for free, but if you do not have your own, you can utilize one of the tour companies that specializes in snorkeling. The tours are very reasonably priced and will take you to some of the best reefs for snorkeling. If you can, pick up an underwater camera to take advantage of some great underwater photo opportunities.

• Duval Street – Whatever you do while in Key West, you really must take a walk down Duval Street. It’s about 1 mile in total and is home to some interesting shops, bars, cafes and other unique ‘visual stimuli’ that you don’t want to miss.

• Sloppy Joe’s – Sloppy Joe’s  is one of Key West’s best-known bars and is famous for one of its local patrons, Ernest Hemmingway. The historic bar contains many personal items that once belonged to the celebrated author. The bar has a very storied and interesting past, dating back to Prohibition, which by the way, didn’t stop anyone from drinking in Key West!  Hemmingway was actually the person who suggested the name Sloppy Joe’s after Jose (Joe) Garcia Rios Havana Club that sold iced seafood and liquor. Since the floor there was always wet because of melting ice, the name Sloppy Joe’s was born.

• Mallory Square – Mallory Square is a plaza off the northern end of Duval Street at Wall Street. This is a popular place since the cruise ships dock here. With many restaurants and shops, cap off your walk down Duval Street with a stop here. The area is popular in the evening, not only for the beautiful sunsets, but also because of all the performers that come out to entertain the crowds.

TIP: Don’t forget to try the quintessential dessert of Key West, a slice of Key Lime Pie. Many restaurants will have it on their dessert list or stop by the Key Lime Pie Company.

• Southernmost Point of the Continental United States – The Southernmost Point is marked by a concrete buoy with the famous line that states “90 Miles to Cuba”. Each evening people gather here to watch the sunset and the area takes on a carnival atmosphere. And, of course, you must take the iconic photo standing next to the buoy.

• The Ernest Hemmingway House and Museum – Ernest Hemmingway lived in Key West from 1928 to 1940, but was a frequent visitor throughout the 1940s and 1950s. The Hemingway House provides an interesting look at the author, along with his writing studio where he wrote many of his most famous novels. The home also boasts a swimming pool that cost $20,000 in 1938 and was considered an extraordinary luxury at the time. While you wander the grounds to enjoy the lush gardens, be sure to check out some of the more than 40 six-toed cats that are decedents of Hemmingway’s first polydactyl cat, Snow White. These kitties are all very friendly and they receive exquisite care from the staff and local veterinarians.

• Truman’s Little White House – Truman’s Little White House was originally constructed in 1890 as naval officers housing. Harry Truman used the home as the ‘winter White House’ and spent 175 days of his presidency there from 1946 through 1952. Other presidents have also stayed at the home including Eisenhower, Kennedy, Carter and Clinton.

The tour was thought-provoking in terms of its historical perspectives, and the guides do an excellent job of explaining the issues and concerns of that time period. Since the home is maintained pretty much as it was during Truman’s presidency, it was really quite interesting to see how the first family lived while in Key West. Guided tours begin about every 20 minutes and last an hour.

• Sunset Sail Tour – Things always look different from the water, and a sunset sail is an adventurous way to see the sites of Key West from a different perspective. There are several companies that offer sunset cruises.  Most will last about 2 hours and offer beverages (including beer, wine and sometimes margaritas). Some tours will also include some light appetizers and live music. So, if you would like a chance to get out on the water, consider a sunset cruise.

• Key West Lighthouse – Located about a block off Duval Street and almost across the street from the Hemmingway House, is the Key West Lighthouse. The lighthouse was completed in 1848. Visitors can explore the grounds and climb the 88 steps to the top of the lighthouse. It’s also an opportunity for some great aerial views and photos of Key West.

• Fort Zachery Taylor – Located on the south side of Key West, Fort Zachery Taylor  predates the Civil War and contains the largest cache of Civil War armaments in the world. On the third weekend of each month local re-enactors conduct historic demonstrations in the fort.

• Bike Tour – Although you can walk all around Key West, it can be a bit of a workout, so why not try a bike tour? There are many local companies from which to choose. Not only will you get from place to place faster, but a local tour guide will explain the history of each place you visit. Key Lime Bike Tours, Paradise Bike Tours and Lloyd’s Tropical Bike Tour are just a few of the most popular companies

• Mel Fisher Maritime Museum – Located near Mallory Square, Mel Fisher Maritime Museum  houses a vast exhibit of maritime artifacts. Learn about Mel Fisher and his 16-year quest to find the sunken Spanish treasure galleon, the Atocha, which sank off the Keys in 1622. Other exhibits include a treasure gallery and the science of shipwrecks.

We hope you have the opportunity someday to visit this unique city, with all of its eccentricities. With so much to do, it will be a destination you will want to return to time and time again!