Key West, the last stop in the Florida Keys, is the southernmost point of the United States. It has a legendary past. If the coral reefs could talk, you’d hear fascinating tales. Stories such as those of Spanish explorers, pirates, smugglers, devastating hurricanes, famous people like Ernest Hemingway and Harry S. Truman, economic booms, declines, and recoveries. Speaking of reefs, Key West is home to the world’s third-largest barrier reef. It’s a tourist destination that oozes history and charm.
Whether you visit for the day or a week, walk along Duvall Street to taste some delicious food, enjoy libations, and hear live music. Take a historic trolley ride and stop in Mallory Square to marvel at the sunset (or follow an insider’s tip on other locations). Don’t miss a guided stop in one of the Conch Republic’s historical sites to discover nautical or American history. The following are seven fantastic things to do (in no specific order). Even if you experience a few, you’ll enjoy an epic trip.
I was a guest at the Florida Keys and Key West Visitor’s Bureau for this visit, but all opinions are my own.
1. Taste Rum From Papa’s Pilar — Hemingway Rum Company
Papa’s Pilar Rum Distillery is a great stop on your visit to Key West. The ultra-premium, award-winning rum is crafted onsite at this facility that is just yards away from where Ernest Hemingway docked his beloved boat, Pilar. His larger-than-life persona inspired the brand with the blessing and involvement of Ernest’s son Patrick who is involved in aspects of the operation. For fans of the writer, you’ll love the stories, and the rum is exceptional.
A Tour, Tasting, And Cocktail Class
When you book a tour online (singles, couples, or small groups), you’ll learn about the rum-making process and discover more about the man, the myth, and the legend who inspired the brand. The tour takes forty-five minutes and is interactive. You’re invited to hear stories, smell, taste, and touch the product as it “moves” through the distillation process from barrel to the unique bottle that is shaped like a World War II canteen. Afterward, you’re treated to a craft cocktail using one of the three rums produced at the distillery. A cocktail-making class includes a tour, tasting, and instruction to make two different drinks with a cocktail specialist. Cocktail classes require proof of age and a separate booking.
2. Ride On The Historic Conch Tour Train
The Conch Tour Train is legendary in Key West and a must-do if you want to see Old Town combined with a narrated description of the landmarks. The train has been operating since 1958. This open-air tour offers a narrated experience for 75 minutes, departing the station every half-hour. You can hop off at designated spots to do some sightseeing and catch a later train to finish your tour throughout the day.
Cover The Must-See Landmarks, Museums, And Attractions
Pay for a ticket at the Front Street Depot (there are accessible trains for handicapped riders) and start the tour around Old Town. The train makes three stops. One to hop off for food and non-alcoholic refreshments (allowed on the train). Other stops are for sightseeing, including Truval Village, close to Ernest Hemingway’s home, The Key West Lighthouse, the Southernmost Point, The Butterfly, and Nature Conservatory, art galleries, and the shops on Upper Duval Street. Return to designated stops to finish your tour. End your time at Mallory Square to enjoy the vendors at the open-air market. It’s a terrific way to see a lot of what Key West has to offer while hearing about the history along the way.
3. Visit Ernest Hemingway’s House
The author and journalist Ernest Hemingway lived in Key West throughout the 1930s. He and his second wife Pauline purchased the deteriorating Tift mansion in 1931, making extensive renovations as it sat uninhabited for over 40 years. Hemingway was an avid fisherman, often taking his boat, Pilar, out to catch Tarpon and Marlin along the Gulf Stream between Key West and Cuba. Pilar’s captain, Gregorio Fuentes, became the inspiration for one of his famous novels, “The Old Man And The Sea”, which won a Pulitzer Prize in 1953 and the Nobel Prize for Literature in 1954. Hemingway was a larger-than-life figure who lived here until his divorce from Pauline in 1940. Many of his possessions that were collected from his travels, plus several descendants from his first six-toed cat, Snow White, are still in the home today.
Learn About The Man Behind The Legend
Tours take place daily (365 days a year) and don’t require reservations. Only cash is accepted at the gatehouse. Once inside, the guided portion takes around 30 minutes and includes many of the rooms in the Hemingway home. Visitors begin walking in the parlor, the bottom floor, and continue up the stairs to the private chambers where the Hemingways raised their sons Patrick and Gregory. You’ll experience a beautifully restored mansion from 1851 and learn more about the complicated yet exuberant man behind his novels. Outside you can enjoy walking around his “expensive” pool or head up the metal stairs to Hemingway’s writing loft where more personal things are housed. A bookstore on the premises sells his titles, posters, and souvenirs. You can wander the grounds for as long as you like.
4. The Key West Lighthouse
Just a short walk from Hemingway’s home is The Key West Lighthouse. It’s the second lighthouse, as the first one washed out to sea in 1846 during a hurricane. There are 88 steps to the top, which is the highest point on the island, and where you can enjoy stunning views over Key West and (up to 15 miles) the ocean. Your ticket includes a stop at the restored Keeper’s Quarter Museum to learn about the first woman lightkeeper, nautical artifacts, antique furnishings, maps, and vintage photos.
A Fascinating View From The Southernmost Point Of The United States
The Lighthouse Museum is on the National Register of Historic Places as the US Navy established a base in Key West in 1823. Shortly after, a lighthouse became necessary to ensure safe arrival for naval and commercial vessels because there was a wreck at least once a week. Over the years, a newer lighthouse was constructed and saw the first woman as a lightkeeper in 1848. The lighthouse was decommissioned in 1969. Another great tour is a memorable sunset experience available for small groups booked 48 hours in advance. It includes wine and charcuterie along with the fabulous view.
5. The Southernmost Point
The Southernmost Point is a painted marker denoting that the location is the furthest southern point in the United States and that it’s 90 miles from Cuba. It makes for a great photo opportunity. Get to the intersection of Whitehead and South Street early in the day before the line begins to form and smile for a selfie. Another option is to visit when everyone is enjoying the sunset at Mallory Square. It’s a must-do.
6. The Little White House
The Little White House was a second home to President Harry S. Truman. He spent 175 days of his presidency here from 1946-1952, and it is the only presidential site in the state of Florida. Originally an officer’s quarters for the Navy in the 1890s, it became the winter home of Truman and his family. Still, other presidents stayed here and used it for political meetings, peace talks, or rest. Political figures such as John F. Kennedy, Dwight Eisenhower, Jimmy Carter, and Bill Clinton have used the home. Today’s guests can tour, learn about the Truman family, and see artifacts from Truman’s life spent on Key West. His original presidential limousine is on display and is available for rides with a VIP White Glove Tour.
7. Audubon House And Tropical Garden Tour
Frequent shipwrecks gave way to a profitable shipwrecking industry in the 1800s. The maritime pilot and wrecker Captain John Huling Geiger became wealthy from the trade. He built a grand home in the 1840s known as Audubon House. It was slated for demolition and saved by the Mitchell Wolfson Family Foundation in 1958. Today, the stately restored 19th Century home, including original Audubon hand-painted lithographs and a lush tropical garden (voted the best outdoor location for private parties in Key West), is open for tours. The one-acre property showcases orchids, bromeliads, and other plants creating an incredible oasis in the heart of downtown. The restoration in 1958 sparked the restoration movement in Key West.
Pro Tips
For more information about the Keys or Key West, click here. For a great meal with water and sunset views, dine at the Half Shell Raw Bar. The ambiance is relaxed and fun. The fish is freshly caught and the oysters are shucked to order. They’re one of the originals and a favorite spot among captains and locals.
Many visitors head to Mallory Square to enjoy street performers, musicians, and the must-see sunset experience. For a more relaxed, less crowded sighting, head to the Sunset Tiki Bar at the Galleon Resort for live music and tropical cocktails.
The original haunt of Ernest Hemingway is Captain Tony’s Saloon, which used to be called Sloppy Joe’s. It’s the oldest bar in Key West with tons of history and a great stop for live music.
For more tips on traveling to Key West, check out these articles: