Things To Do In Key West On Vacation

Ultimate Key West 3-Day Weekend Itinerary

Nothing is more thrilling than the prospect of a long weekend around the corner. Since the two most prominent holidays that feature that most welcome Monday off, Labor Day and Memorial Day, occur in the warmer months, visions of outdoor grills, swimming pools, and chilling hard on the old Barcalounger are among the most desirable. However, if you decide you want to level up from the common ‘staycation’, there’s an island situated in the southernmost reaches of the Sunshine State that has been delighting visitors for decades. With its pioneer spirit, off-the-grid appeal and beach town charm, Key West is your ticket to adventure!

Hop On Hop Off Key West Tours

Hello, I’m Rich Fox, General Manager of Old Town Trolley of Key West. The sun, quaint setting, and clear waters of Key West have lured visitors since its settlement in 1822. For over 30 years, Old Town Trolley Tours has provided sightseeing tours highlighting the best Key West attractions. Hop aboard one of our trolleys and you’ll experience Transportainment, a delightful combination of transportation and entertainment. Our friendly conductors narrate the tour with a fascinating and fun mix of trivia and humorous stories.

Romantic Things To Do in Key West

Spectacular sunsets, warm ocean breezes and a laid-back island atmosphere create the perfect setting for a budding romance or rekindling a long-term relationship. These are some of the enduring images and themes featured in many of Hollywood’s most romantic movies. Key West offers this and more. A favorite destination for royalty, political leaders and literary legends, this tropical oasis is an idyllic backdrop for a first date or special getaway celebrating a long-term relationship. Take that special someone on a romantic, unforgettable trip to experience attractions that allow couples to enjoy the sights while spending quality time together. 

Custom House Key West

Looming over Mallory Square near the Margaritaville Resort & Marina, the Custom House is an iconic Key West institution. An imposing four-story, red brick structure built in 1891, it’s a sight easily recognizable from land and sea. Originally home to Key West’s post office and district courts, today the Custom House is a fascinating museum run by the Key West Art & Historical Society. Their mission is to preserve the culture of the Florida Keys through the exhibition of art, architecture and history to educate the community and visitors.

Perfect Girls Weekend Key West

Planning a girls weekend in Key West? We’ve got you covered with everything from where to stay, what to eat, the hottest bars and the best activities on the island.

Things to Do During the Fall

While seasons matter when you’re planning a vacation in most places around the world, any time of the year is a great time to visit Key West. In the fall, the island cools off just a bit and beckons people from all walks of life to come experience its majesty. If you’re planning a vacation to the southernmost city in the fall, this guide will provide you with all you need to know.

Dry Tortugas National Park Ferry

The Yankee Freedom III is the official ferry of the Dry Tortugas National Park. 70 miles from Key West at the Dry Tortugas National Park lies Fort Jefferson, the largest masonry structure in the western hemisphere. Aboard the Yankee Freedom guests will travel in air conditioned comfort, enjoy delicious breakfast and lunch, snorkel gear, showers and guided tours of this Civil War fort that has been called the eighth wonder of the world.

Key West Beaches

If you are planning a Key West vacation, spending some quality time at the beach is a top priority on your travel itinerary. Boasting temperate waters and more than 3,400 hours of annual sunshine, the beaches of Key West are some of the most popular destinations on this tropical island paradise. You can enjoy the sun, sand and warm water as well as a variety of activities like swimming, snorkeling and fishing.

Dry Tortugas Interpretive Center

The Museum is a free attraction located in Key West’s Historic Seaport, known as the “Bight.” Exhibits include an 11-foot diameter scale model of Fort Jefferson, an interactive photo mural that explores the history of the Bight and a Junior Ranger Exploration Station that allows children to get hands-on with and learn about the natural resources of the Dry Tortugas.

Things To Do Near The Southernmost Point

Key West is famous for being the southernmost city in the continental United States. When you visit, it’s essential that you make it to the southernmost point on the island, found at the intersection of Whitehead Street and South Street. Here, you’ll see the landmark Southernmost Buoy (a required photo opp) and a whole host of other “southernmost” attractions that make for a fun Key West afternoon.

Ultimate Guide To Duval Street Key West

Perhaps one of the most popular destinations on the island of Key West, Duval Street is the main drag of downtown, running north and south from the Gulf of Mexico to the Atlantic Ocean. Although it is not much more than a mile in length – this is where the heartbeat of the city comes to life with a diverse array of restaurants, shops, world famous pubs and attractions.

Things To Do In Key West Near Mallory Square

Witness one of the world’s most majestic settings at Mallory Square. Here’s where everyone comes to see, eat, shop and linger. Buy a locally collected sea sponge, peruse a Wyland original in the gallery and stop in at the famous Hog’s Breath Saloon. Mallory Square is where it’s all at and where it all comes together. It’s also where the evening transforms into the renowned sunset celebration and when street performers, colorful entertainers and mouth-watering foods emerge as the sun begins to descend. Browse through the unique shops, pick up a souvenir at Ron Jon Surf Shop and see the local attractions. Find out what all the excitement is about.

Fort Zachary Taylor State Park

Designated a National Historic Landmark in 1973, Florida’s southernmost state park is popular for recreation, as well as U.S. military history. The fort was one of a series built in the mid-1800s to defend the nation’s southeastern coastline. Guided tours of the fort are available daily.
100 Southard Street

Key West Ghost Tours with Ghosts & Gravestones

Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town – filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America.

Key West Cruise Excursions

Welcome to Key West

Key West is a beautifully historic town filled with impressive attractions and sites. Maximize your time for sightseeing by taking Key West shore excursions from Old Town Trolley. Whether you take the tour purchased from your cruise excursions desk, or take the tour with on-and-off privileges purchased from Old Town Trolley directly, you will have time to shop, visit attractions, and find your way to some of our most famous landmarks.

Things To Do With Family

There’s always something happening in Key West and the year-round sunshine makes it easy to do it all! If you’re looking for a variety of fun things to do in Key West with family, the Southernmost City is a great place to go. Check out some of the most popular family activities on the island.

Things to Do in Key West During the Winter

There’s no place on earth quite like Key West, especially during the winter. While the weather does get a bit milder from November through February, you’ll still experience bright sunny days and refreshing ocean breezes. Fun activities and special winter events are in no shortage. Read on for the top things to do during winter in Key West.

Things to Do in Key West During the Spring

Is there ever a bad time of year to visit Key West? Of course the answer is no; but springtime is one of the best times of year to head to this island paradise. The skies are sunny, the water is warm and the attitude is as welcoming as it always is. There is a ton of fun in store for you in the Southernmost City. Read on for the top things to do in Key West in the spring.

Things To Do With Kids in Key West

Looking for the most efficient and entertaining way to visit many of the things to do in Key West with kids? Look no further because Old Town Trolley Tours offers parents a relaxing way to tour all the best Key West attractions for kids. Parents don’t have to worry about searching for directions to the Key West Aquarium, driving to White Street Pier and Higgs Beach, or finding parking while traveling from all of Key West’s best attractions. Our hop on and hop off trolley tours allow the parents to concentrate on having fun with their kids instead of worrying about logistics.

Sloppy Joe’s

The famous Sloppy Joe’s Bar is more than just a local watering hole where you can stop in for some live music, cold drinks and good food, it’s a Key West tradition. A gathering place where locals and visitors mesh, this well-known bar has hosted thousands of patrons through the years, the most celebrated being Ernest Hemingway. A visit to the Southernmost City is incomplete without a stop into Sloppy Joe’s Bar – but before you go, check out this guide.

Things To Do In The Summer

It’s summer and there’s no place more exciting to be than in Key West. This tiny island paradise is one of the most unique places on earth, where people from all walks of life come to let loose and have an unforgettable experience. But it’s summer and it’s South Florida! It is a good idea to plan on visiting some of the indoor attractions and sights to stay cool.

Sails to Rails at Flagler Station

Relive the time in America when railroads opened up the frontiers of an emerging nation. Railroads meant a connection to commerce, wealth, and politics in the young country. In a sense, the United States of America was built on the foundation of its railroads, and Florida was certainly no exception.

Yankee Freedom III

Experience a journey like no other aboard the Yankee Freedom III. Take your comfortable seat and enjoy the relaxing ride to the Dry Tortugas National Park Fort Jefferson, just 70 miles west of Key West. The Yankee Freedom III is recognized for its speed and luxurious accommodations and for transporting thousands of visitors annually to the beautiful collection of islands called the Dry Tortugas.

Key West Botanical Garden

The Key West Tropical Forest & Botanical Garden is the only frost-free sub-tropical native botanical garden in the continental United States. Here you can see many endangered and threatened flora and fauna. A beautiful and serene respite, this special place will take you back in time and allow you to be among butterflies, birds, plants and seasonal flowers.

Ernest Hemingway House

This lovely Key West home is where legendary author Ernest Hemingway lived and worked for more than ten years. The home and gardens are visited by thousands of people each year, offering a glimpse into Hemingway’s life and a chance to meet some of the descendants of his beloved six-toed cat, Snowball.

West Martello Fort

This historic tower was built in 1862 during the Civil War and is one of three remaining Civil War era structures on the island. Although it was often used for target practice by the United States Navy, the fort was never actually involved in a battle. It is now home to the Key West Garden Club.

Key West Historic Seaport

Key West’s historic seaport has long been a hub of activity on the island. Hundreds of years ago, sea captains found the area a useful and safe stopping point in their journeys. It was the epicenter for industries including sea turtle fisheries, shrimp and sponge fisheries. Today, the area has maintained its charm, with a lovely mix of old and new and offering visitors not only a scenic view but also a variety of unique attractions in the midst of restaurants, shops and activities.

Tropic Cinema

For those who love film and not the mainstream box-office variety, Tropic Cinema in Key West has got a ticket just for you. The theater was founded after a group of disenchanted film buffs got together to bring unique documentary, independent and foreign films to Key West. The group, now called the Key West Film Society, rapidly gained support from the community and soon the Tropic Cinema was created.

San Carlos Theater

As part of the San Carlos Institute, which was founded in 1871 to help the Cuban community in Key West, the San Carlos Theater offers a variety of entertaining productions throughout the year. It’s the first and oldest theater in Key West, and was once a home to touring ballets, opera and theater companies. Today the San Carlos Theater, after a magnificent restoration, offers concerts and other theatrical events.

Oldest House Museum

The oldest house in South Florida was built in 1829 by Captain Francis Watlington who was, among other things, a wrecker. Watlington and his wife and their seven (of nine) surviving daughters lived in the house for many decades. A beautiful example of the kind of colonial architecture found in the Caribbean, the house is now a museum that welcomes visitors from around the world. Guests see gold that was salvaged from shipwrecks, paintings, model ships and a separate kitchen. Furnishings, carpets and the house décor all reflect the era of the wreckers and their success that made Key West the richest city in America at one time. There’s also a lovely garden with benches offering a shady spot to rest and relax. Learn a little history, admire the ancient architecture and more at the Oldest House Museum.

Ripley’s Believe It or Not!

What could be weirder than a two-headed animal or a man standing almost 9 feet tall? Find out at Ripley’s Believe It or Not!

Key West Cemetery

After seeing some of the city’s most colorful and quirky characters on Duval Street and in Mallory Square, take a moment to visit the Key West Cemetery, where it is said that close to 100,000 original Key Westers are buried. It’s an excursion that offers history, at the bast of lighthearted humor. Located on Solares Hill, which is the highest point of elevation on the island, the cemetery opened in 1847 after bodies from the original cemetery washed ashore during a storm. Stroll through the 19 acres and see if you can find the headstone that reads “I told you I was sick”, or “At least I know Where He’s Sleeping Tonight”.

Key West Fury Water Adventures

People from all over the world come to Key West for the unique atmosphere, world-famous attractions and, of course, the refreshing turquoise waters that surround the island. Whether you’d like to dive in and snorkel, fly above the water in a parasail, go on a glass-bottom boat excursion, take a sunset cruise or try your hand at jet skiing, Fury Catamarans offers a myriad of exciting adventures.

Southernmost House

One of the most striking and distinctive buildings in Key West, the Southernmost House proudly sits at a prime location overlooking the Atlantic Ocean at the quieter end of Duval Street. This impressive example of Queen Anne-style architecture is just one of many iconic Key West attractions. Boasting a long history of hospitality, this building is now a historic adult-only bed-and-breakfast situated on the edge of the Old Town District. The inn boasts a retro, pastel-colored exterior, elegant gables and bold landscaping. It is the southernmost private residence in the United States. Although a few other living quarters are further south, they are located on the Key West Naval Station and are not open to the public. The hotel is one of the most-photographed buildings in Key West.

Southernmost Point

Key West is famous for being the southernmost city in the continental United States. When you visit, it’s essential that you make it to the southernmost point on the island, found at the intersection of Whitehead Street and South Street. Here, you’ll see the landmark Southernmost Buoy (a required photo opp) and a whole host of other “southernmost” attractions that make for a fun Key West afternoon.

Key West Butterfly & Nature Conservatory

Located at the southernmost end of Duval Street, the Key West Butterfly & Nature Conservatory is one of the island’s most popular family-friendly attractions. It’s home to more than 60 species of butterflies and 20 species of exotic birds. A visit to the Key West Butterfly & Nature Conservatory is divided between the climate-controlled conservatory where the butterflies flutter freely, the learning center, an art gallery and a gift shop.

Key West Historic Memorial Sculpture Garden

A lasting tribute to the most famous and influential residents of Key West, the Key West Historic Memorial Sculpture Garden is an oasis shared by all who live on the island. Featuring impressive bronze busts of Ernest Hemingway, Asa Tift, Harry S. Truman and others, the garden also includes a scenic walkway paved with memorial bricks that are purchased by local citizens then engraved with their names or the names of a loved one.

Higgs Beach

Hit Higg’s Beach for a true Key West beach experience. A popular beach wedding location, too. Locals love it and so do visitors, including brides who dream of a Key West beach wedding. The white sand and wooden pier make ideal spots for sunbathing and the beach offers umbrella rentals for those who prefer to doze in the shade. There are tennis courts, a restaurant, volleyball courts and more. For the kids, make it a point to stop by Astro City, an awesome playground located just across from the beach.

Key West Glass Bottom Boat

Embark on an adventure to the world-famous reefs off the coast of Key West. Aboard the Pride of Key West — the magnificent Key West Fury catamaran with a glass bottom, you’ll enjoy the fresh sea air as you voyage above the lively marine world underneath. Once you arrive above the reefs, be ready to catch your breath as vibrant sea life abounds right beneath your eyes.

AIDS Memorial

Remembering those who were lost to AIDS, the Key West AIDS Memorial is a touching tribute that makes a lasting impression on all who view it. The names of those who have died from AIDS are inscribed on flat granite which makes a walkway on the way to the White Street Pier. It was dedicated on World AIDS Day in December of 1997 and at that time 730 names were included. Sadly, today there are 1,000 names listed on the memorial – all people who lived, visited or worked in Key West. Each year new names will be engraved until the memorial capacity of 1,500 names is reached. The dedication of the new names occurs on World AIDS Day, which is December 1 of every year. A somber site, many come to remember their loved ones, family or friends.

African American Memorial

Key West was never a slave port, but in 1860, 3 slave ships headed for Cuba were intercepted by the U.S. Navy. 1,432 slaves who survived the transoceanic voyage were brought to Key West for care. Despite the best attempts by the island’s residents, 295 are buried in shallow graves near the West Martello Fort.

Casa Marina Resort & Beach House

The Casa Marina Resort and Beach House is an icon in Key West. It was built by Henry Flagler for his passengers on the overseas rail road in 1920 and exudes splendid Mediterranean charm. Sophistication and luxury mesh beautifully with this ideal Key West locale offering visitors a heavenly retreat in the midst of historic sites, natural beauty and enticing attractions. Ocean view rooms, an expansive private beach and a gorgeous swimming pool make it easy for guests to relax and appreciate every moment of their stay.

Audubon House

The Audubon House marks the beginning of the restoration movement in Key West. Saved from being demolished in 1958, the 19th century Key West gem is a historic museum featuring the artwork of John James Audubon. Famous for his exquisite drawings of birds in their natural habitat, Audubon stayed in the home in 1832.

Smathers Beach

Smather’s Beach is the largest beach in Key West which runs along the southern shore. The beach offers activities such as volleyball and watersport rentals, and vending trucks offer snacks, beverages, chairs, and rafts. There’s plenty of parking, restrooms, chair rentals, picnic tables and more.

Mel Fisher’s Maritime Museum

“Today’s the day” was Mel Fisher’s mantra. Fortunately, his lifelong hunt for ancient buried treasure was realized before he died so his mantra held true. The day was July 20, 1985, when, after 17 years of searching, Mel Fisher and his crew recovered $450 million worth of buried treasure from ocean floor just offshore from Key West. The Nuestra Senora de Atocha and the Santa Margarita, two Spanish galleon ships that sunk in 1622, carried 40 tons of gold and silver, Pieces of Eight gold coins, Columbian emeralds, over 1,000 bars of silver and other gold artifacts.

Customs House Museum

For a bit of history and a look at how Key West got to where it is today, stop in at the Key West Museum of Art and History inside the Custom House. Built in 1891, the Custom House had many uses including a post office, court house and government center. Today, after a $9 million restoration, the beautiful red brick building is as glorious as it was back in the day and is home to moving works of art that portray the colorful past of Key West and historic national events.

Truman Little White House

A place where an array of leaders, legendary inventors, dignitaries, visionaries and many prestigious visitors were drawn to throughout its history, Key West’s Harry S. Truman Little White House holds a special place in the history of America. Constructed in 1890 to serve as the naval station’s command headquarters during the Spanish-American War, World War I and World War II, this historic site later became the second White House.

Key West Yacht Club

The Key West Yacht Club is the Southernmost Private Club in America with 68 wet slips in various sizes, 3 transient rental slips, dock restroom facilities with showers, boat ramp, full service dining room and bar, ships store and gift shop.

Key West Shipwreck Treasure Museum

Feel the exhilaration as you climb 65 feet in the air to the top of the observation tower for panoramic views of Key West. Inside the Key West Shipwreck Treasure Museum, you’ll have that opportunity and more. Find out how those who made their living off shipwrecks in the 1850s watched and waited for ships sinking off the coast in Key West.

Key West Lighthouse

If you’re up for a climb, you’ll be rewarded with stunning views of Key West and the ocean. The Key West Lighthouse was built in 1825 to help the many ships entering the port avoid the hazardous reefs. Today, you can climb the 88 iron steps to the top of the tower for a scenic look at what the lighthouse keepers watched over for more than 120 years. Tour the grounds to see the Keeper’s Quarters which have been restored to their original charm and view the displays of nautical artifacts, antique furnishings, maps and vintage photos.

Key West Aquarium

Welcome to Key West’s first attraction. Meet stingrays and pet a shark! See them eat and watch in wonder as a variety of sea creatures swim around in their natural environment. Come to the Key West Aquarium for an encounter with some of the world’s most mysterious and beautiful marine animals. Since 1934, the aquarium has been wowing guests with its variety of sea species. Listen and learn as knowledgeable guides explain the underwater world that surrounds the Florida Keys.