Nestled at the southernmost point of the continental United States, Key West, Florida, is a vibrant island paradise that captivates visitors with its eclectic charm, stunning sunsets, and laid-back atmosphere. Known for its rich history, diverse culture, and natural beauty, Key West offers a perfect blend of relaxation and adventure for vacationers seeking an unforgettable escape. There are a multitude of fun things to do in Key West . . . here are a few.
Key West Express Ferry
Despite it’s isolated proximity, there are a number of ways to get to Key West. You can drive along US 1 which stretches over 113 miles, includes 42 bridges and takes approximately 4 hours from Miami. You could fly into Key West International Airport (EYW) from a multitude of direct flights throughout the US on a number of major carriers. We chose to take the Key West Express Ferry from Fort Myers Beach. We departed at 8a and the journey took about 4 hours. Onboard amenities included comfortable seating, air conditioning, food and beverages, facilities and stunning views of the Gulf of Mexico. You definitely need to Book in advance, especially during high season and prepare for possible weather-related delays.
The ferry offloads at the Key West Blight Ferry Terminal (Flagler Station). Once you get to the Henry M. Flagler Statue, bear southwest along Caroline Street and start discovering things to do in Key West.
Caroline Street
Caroline Street is the first of many things to do in Key West. It’s one of the notable thoroughfares in Key West known for its rich history, vibrant atmosphere, and proximity to many of the island’s key attractions. Stretching through the heart of Old Town, Caroline Street offers visitors a mix of historic sites, charming architecture, unique shops, and lively bars and restaurants. Caroline Street is lined with beautifully preserved 19th-century buildings that reflect Key West’s historical charm. Walking along the street, you’ll notice the distinct conch-style architecture that characterizes many of the homes and businesses. Five blocks down you’ll encounter one of the most popular things to do in all of Key West . . . the infamous Duval Street.
Duval Street
Duval Street is the most famous thoroughfare in Key West, Florida, known for its vibrant atmosphere, historic landmarks, eclectic shops, lively bars, and diverse dining options. Stretching from the Gulf of Mexico to the Atlantic Ocean, this mile-long street is the heart of Key West’s cultural and social scene. At the corner of Caroline and Duval is the stylish Bull & Whistle Bar, the last of the old-time Duval Street open-air bars. Across the street is the infamous Banyan tree obscuring the historic Dr. Joseph Yates Porter House. As you proceed north towards the pier you start to see some of the more popular haunts like Willie’s Chicken Shack, Durty Harrys, Sloppy Joe’s Bar and Amigos Tortilla Bar. A common thread is the abundance of live music among many of the Duval Street establishments. Your journey north ends at the Glassbottom Boat at the water’s edge.
As you head back south on Duval Street, at the corner of Front St. is a beautiful Art Deco building. It was first built as a bank in 1891 by Cuban cigar factory owners and also the bank robbed in Ernest Hemingway’s novel “To Have and Have Not.” You’ll see the beautiful Gothic Revival style St. Paul’s Episcopal Church, established in the 1830’s, the fourth church on this site, as previous structures were destroyed by hurricanes and fires. A block away is Jimmy Buffett’s original Margaritaville bar, restaurant and gift shop. Across the street is Willie T’s and its time honored tradition of visitors penning messages, or their names, on dollar bills and attaching them to the walls and ceiling . . . definitely one of the coolest things to do in Key West.
You’ll find quirky spots like Moe’s Way, named for Melvin “Moe” Marks, a beloved figure in Key West, known for his contributions to the community. There is culture, like the Guild Hall Gallery, the classical Conch architecture of the Pinchers Restaurant building and the quirkiness of the 801 Bourbon Bar abutting the Rainbow Crosswalk. Further south on Duvall Street are some of the more well known things to do in Key West like the Hemingway House, the Southernmost Point Guest House and Duval Street Pocket Park.
Amigos Tortilla Bar
For lunch we choose Amigos Tortilla Bar, a popular spot in Key West, Florida, known for its fresh Mexican cuisine, laid-back atmosphere, and prime location right off the iconic Duval Street. Amigos has a casual, fun, and lively atmosphere. The open-air seating lets you enjoy the warm Key West weather, and the friendly staff makes you feel right at home. The restaurant features colorful and vibrant decor with Mexican-inspired artwork and a cozy, welcoming ambiance. Amigos is best known for its fresh, homemade tortillas and authentic Mexican flavors. Be sure to try the Taco Trio, a selection of three tacos, allowing you to mix and match different fillings such as grilled chicken, steak, pork, or fish. With lots of options, you should add Amigos to your list of things to do in Key West.
Santa Maria Suites Resort
Santa Maria Suites Resort is a luxurious and highly-rated resort in Key West, Florida, offering guests a perfect blend of comfort, elegance, and convenience. We stayed in the 2 Bedroom Flat with a pool view. The rooms were well laid out, roomy and immaculately appointed. There was a spacious common area complete with sink, refrigerators, a microwave, Keurig coffee machine, couches, love seats and even an additional bed. The pool area was open with both pool and hot tub as well as a server dispensing drinks for hotel guests on request. We highly recommend the Santa Maria Resort.
The Hemingway House
The Ernest Hemingway Home and Museum should top a list of things to do in Key West for literary enthusiasts, history buffs, and tourists alike. This beautifully preserved property offers an intimate glimpse into the life of one of America’s most celebrated and controversial authors, surrounded by lush gardens and home to a unique population of six-toed cats. Ernest Hemingway lived in this Spanish Colonial-style mansion from 1931 to 1939. Purchased for him by his wife, Pauline Pfeiffer, the house became a retreat where Hemingway wrote some of his most famous works, including “To Have and Have Not” and “The Snows of Kilimanjaro.” Built in 1851, this architectural gem features limestone construction, spacious verandas, and elegant French windows.
The interior is filled with antiques and artifacts collected by Hemingway during his travels, giving visitors a sense of the author’s eclectic tastes and worldliness. The home is meticulously maintained to reflect the period during which Hemingway lived there. Each room is filled with original furniture, family photographs, and memorabilia that transport visitors back to the 1930s. Highlights include Hemingway’s writing studio, where he penned many of his classics, and the master bedroom, with its antique bed and luxurious decor. Visitors can take guided tours of the house, led by knowledgeable guides who share captivating stories about Hemingway’s life, his works, and his time in Key West.
The lush gardens surrounding the home are a tranquil oasis filled with tropical plants, vibrant flowers, and a serene swimming pool—the first in-ground pool in Key West. The gardens provide a peaceful setting for visitors to relax and enjoy the beauty of the property. The pool itself has an interesting history, with a story that Hemingway, in a moment of frustration over the costs, threw a penny into the wet cement, declaring Pauline could have his last penny—a penny still embedded in the poolside cement today. Keep an eye out for the Key West Lighthouse visible from the south side of the property and visit the small Museum near the pool.
One of the most unique and charming aspects of the Hemingway Home is its population of polydactyl (six-toed) cats. These cats are descendants of Hemingway’s original pet, Snow White, a gift from a ship captain. Today, around 40 to 50 cats reside on the property, all carrying the genetic trait of polydactyly. The cats are well cared for and are an integral part of the home’s allure, often seen lounging around the gardens and interacting with visitors. In truth, there is scarcely an area on the grounds where you won’t see one of the cats. Of note . . . for obvious reasons, you won’t see any of the infamous Key West Chickens on the Hemingway property.
The Key West Lighthouse
When you exit the Hemingway House just pop right across the street for yet another of the best things to do in Key West. The Key West Lighthouse and Keeper’s Quarters Museum is a historic landmark that offers visitors a glimpse into the maritime history of Key West. The lighthouse rises 73’ tall and takes 88 steps to reach the top, where you’ll be rewarded with breathtaking views of Key West and the surrounding waters. From the top, you can see the entire island, including the historic Old Town, the harbor, and the Atlantic Ocean. The original Key West Lighthouse was completed in 1825 and was rebuilt in 1848 after being destroyed by a hurricane. The Keeper’s Quarters, now a museum, was built in 1887 and has been restored to reflect the life of the lighthouse keepers and their families.
Southernmost Point of the Continental U.S.A.
The Southernmost Point of the Continental United States is one of the most iconic landmarks in Florida and sure to be near the top your list of things to do in Key West. This popular tourist attraction marks the southernmost tip of the contiguous United States and offers visitors a unique photo opportunity and a chance to experience a symbolic geographical point. The Southernmost Point marker, installed in 1983, is a large, colorful buoy-like structure that stands approximately 12’ tall and is actually closer to Havana than to Miami. This proximity highlights the unique location of Key West at the crossroads of the Gulf of Mexico and the Atlantic Ocean.
The Key West Butterfly & Nature Conservatory
The Key West Butterfly & Nature Conservatory is a magical destination that offers visitors a chance to immerse themselves in a tropical paradise filled with vibrant butterflies, exotic birds, and lavish plants. It is home to over 50 species of butterflies from around the world, including Monarchs, Swallowtails, and more. The conservatory simulates a natural habitat with lush tropical plants, cascading waterfalls, and peaceful music, creating a serene environment where butterflies freely fly around you. In addition to butterflies, the conservatory houses colorful exotic birds like flamingos (Rhett and Scarlett), finches, and Chinese painted quail. There is also a Learning Center where you can watch butterflies emerge from their chrysalises as well as a Gift Shop.
The Little White House
The Little White House in Key West, Florida, holds a significant place in American history as a retreat for several U.S. presidents. It served as a winter retreat for President Harry S. Truman during his presidency and was later used by other presidents, including Dwight D. Eisenhower and Jimmy Carter. Truman made several important decisions while staying at the Little White House, including the desegregation of the military and the establishment of NATO. The house has been meticulously restored to its 1940s appearance, with original furnishings, artifacts, and memorabilia on display. There are guided tours that include authentic artifacts, photographs, and documents related to the presidents who stayed at the house, including Truman’s famous “The Buck Stops Here” sign.
Fort Taylor
Fort Zachary Taylor Historic State Park, often referred to simply as Fort Taylor, was built in the mid-19th century and has been designated as a National Historic Landmark. The fort played a significant role in the Civil War, serving as a Union stronghold and a base for naval operations. Among the features of the fort are its massive walls, artillery batteries, and casemates, which have been preserved and restored to their original condition. You can explore the fort’s exhibits, which showcase artifacts, weaponry, and historical information about its construction and military operations. Enjoy a climb to the top of the fort’s walls for panoramic views of the surrounding park, Key West Harbor, and the Atlantic Ocean. You can even walk down to the park’s sandy beach, swim in the clear waters, or snorkel along the rocky shoreline.
Key West Beaches
On your list of things to do in Key West, spending quality time at the beach should rank pretty high. With temperate waters and over 3,400 hours of sunshine annually, you can soak up the sun, relax on the sand, and enjoy the warm water, along with a variety of activities such as swimming, snorkeling, and fishing. Key West is a large coral key, making it essentially a giant rock above ocean level. As a result, the beaches are actually man-made. In addition to the Fort Zachary Taylor State Park Beach, other popular spots are Smathers Beach, Higgs Beach, South Beach and Dog Beach. A fun place to watch the tide come in is the Duval Street Pocket Park.
Dry Tortugas
Exploring Dry Tortugas National Park from Key West is an unforgettable experience, offering a unique blend of history, nature, and adventure. You can either ferry, charter a private boat or, as we did, take a seaplane. The latter not only gets you there faster but the views to and from are spectacular. While on site you can join a guided tour of Fort Jefferson, a Civil War-era fortress and prison, and the largest brick masonry structure in the Western Hemisphere. Or you can explore the fort at your own pace, marveling at its architecture, cannons, and historic exhibits. Don’t forget to climb to the top of the fort for panoramic views of the park and surrounding waters. The highlight is the local snorkeling where you’ll encounter vibrant coral reefs teeming with marine life like colorful fish, sea turtles, and other aquatic creatures. The Tortugas are also ideal for birdwatchers, whale watching or just relaxing on the pristine sandy beaches.
Key West Chickens
The presence of chickens, often referred to as “Key West chickens,” roaming freely throughout Key West, is a unique and iconic aspect of the island’s culture and history. Key West’s chicken population has deep historical roots. Chickens were brought to the island by early settlers and immigrants, particularly those from Cuba and the Bahamas, who raised chickens for food and cockfighting. Over time, some of these chickens escaped or were released, leading to the establishment of feral chicken populations throughout the island. In 2004, the Key West City Commission passed an ordinance designating the chickens as a “protected species.”
Key West is a unique gem at the southernmost point of the continental United States, celebrated for its distinctive blend of natural beauty, vibrant culture, and rich history. This tropical island paradise offers a laid-back lifestyle, epitomized by its motto, “One Human Family,” which emphasizes inclusivity and community spirit. From great food and entertainment to history and culture . . . there are endless things to do in Key West.
