Things To Do In Key West On Vacation

Ghosts & Gravestones Tour

Purchase discount tickets online for the Ghosts and Gravestones Key West tour. Nighttime access into some of the most haunted sites in Key West.

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 Shipwreck Museum

Relive 500 years of Florida Keys history at the new Sails To Rails Museum in the Historic Seaport. Learn how tall ships and Henry Flagler’s railroad made Key West one of the richest cities in America.

The 10 Best Scenic Views and Instagrammable Spots in Key West

There are certain places around the world that just love to be photographed. Key West, Florida is definitely in the conversation when it comes to Insta-worthy spots that a camera’s lens just can’t get enough of. Check out our list of some of the best places to snap some memorable moments in the Conch Republic!

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!

Sails to Rails Museum

Relive 500 years of Florida Keys history at the new Sails To Rails Museum in the Historic Seaport. Learn how tall ships and Henry Flagler’s railroad made Key West one of the richest cities in America.

Holiday Light Contest

Historic Tours of America invites home owners to enter into our friendly competition for the most beautiful house on the block! People of all ages will delight as Key West homes dazzle with their holiday lights adorning every corner of the island. And our sleighs for the night will take guests to some of the most resplendent island homes. This is your opportunity to shine and have the chance to win one of our three cash prices!

The Best Shopping in Key West

In the land of key limes, errant roosters, partying and sunsets, every day is never the same as the one before. With its turquoise waters and hang-loose state of mind, time moves differently here in paradise and that is a very good thing. It’s an easy place to visit but is it ever tough to leave. You forget about the rest of the world here, but you are reminded of it just enough. If you plan on visiting the Conch Republic and want to drop some coin on a bit of a shopping spree, this tiny island is big on options.

Key West For The Holidays

Much in the same way Harry S. Truman retreated to his Little White House when things got a little too cool for comfort up in DC, Key West is where Santa comes to spread cheer and hang out in his Christmas-themed board shorts. This is one of the best places on Earth to celebrate the holiday season, just ask Conchy The Sandman and Rudy The Bottle-nosed Dolphin!

Key West Holiday Tours

No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Lights & Sights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition.

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. 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.

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.

The 6 Best Beaches in Key West – The. Best. Escape. Anyone. Can. Have.

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.

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.

Hidden Gems In Key West

An island of only five square miles, Key West is a pretty easy place to navigate. It’s also filled with hidden gems ripe for discovery.

To paraphrase former Key West resident and famed poet Robert Frost, the road less traveled in Key West can make all the difference. And that’s exactly what you get when you hop aboard Old Town Trolley – the road less traveled far beyond Duval Street.

Casa Marina Resort Guide

The Casa Marina 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. The Casa Marina recently emerged anew, even grander, after a magnificent renovation of the guest rooms, pool and other areas and is now part of the Waldorf Astoria collection of hotels.

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

Get MORE out of your summer in Key West aboard the iconic Old Town Trolley and see the best first!

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.

Key West Museums

Come to Key West for the tropical breeze and sandy beaches; stay for the unique history on display at the southernmost island’s museums.

Things To Do In Key West On Vacation

Some of the most popular Things To Do In Key West include touring the historic museums, relaxing on the beach, and watching the sunset at Mallory Square.

Key West Attractions

Explore Key West attractions with Old Town Trolley Tours. Hop on and off at interesting places to visit and maximize your vacation time.

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

Mallory Square Sunset Celebration

Located at the center of the historic Key West waterfront, Mallory Square Things to do is filled with attractions, unparalleled shopping, fabulous restaurants and the world famous sunset celebration. You haven’t visited Key West until you’ve experienced Mallory Square.

Key West Restaurant Guide

Read the Old Town Trolley guide for foodies to top-rated Key West restaurants. Learn about local dives and popular places to eat for tourists.

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.

Getting Around Key West On Vacation

A visit to Key West is always an adventure and if you’re heading that way, you’re in for great time. The Southernmost City offers a host of interesting things to see and do, fascinating history and gorgeous natural scenery. When you begin your planning, make sure to plan how you’re going to get from one place to another. Here are some of the best ways to get around Key West.

Reasons To Visit Key West

The Southernmost City in the USA, Key West is an oasis surrounded by gorgeous crystal waters. It’s here that you’re invited to come as you are, kick back and let go of all the stresses of hectic day-to-day life. Learn some of the top reasons to visit Key West.

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 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.

Kermit’s Key Lime Pie

Located at 431 Front Street, Kermit’s Key West Key Lime Pie Shoppe was founded more than 20 years ago. Since then, Kermit’s has established a reputation for its tasty Key lime creations – including being recognized as having the best Key Lime Pie by Food Network, National Geographic and Paula Deen.

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

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. 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.

Rick’s Bar

If you haven’t partied at Rick’s Bar, you can’t leave Key West until you do. Located right on Duval, Rick’s is not just a bar; it’s 8 bars – each with its own unique venue and all offering a one-of-a-kind experience.

Labor Day Events

Old Town Trolley Tours of Key West has provided vacation guests and locals with more than 30 years of historic tours, news, and events. Each month the Trolley Team publishes upcoming events in Key West for visitors and residents to enjoy.

Hogs Breath Saloon

On the corner of Duval and Front Streets; The Hogs Breath Saloon is one of those places you just can’t miss while visiting Key West.

How To See Key West in 2 Days

Planning a two-day trip to Key West?

Follow this guide to get the most out of your time on the island.

How to See Key West in 1 Day

So, you’re heading to the southernmost city in the USA? Lucky you! There is so much to do and see in this island paradise, from intriguing attractions and historical sights to water sports, entertainment and world-famous points of interest. If you want to see the best of Key West in one day, hop aboard Old Town Trolley.

Yankee Freedom

Experience a journey like no other aboard the Yankee Freedom. 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 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.

Bahama Village

Get MORE out of your summer in Key West aboard the iconic Old Town Trolley and see the best first!

Get a taste for the Caribbean heritage that is so much a part of Key West. In Bahama Village, which is a 12-block area between Whitehead and Fort and Angela and Catherine Streets, you’ll be able to see the original area in which the first black Bahamian settlers arrived in the 19th century. Sample true Bahamian culinary recipes in a variety of restaurants, stop in for a refreshment in one of the bars and shop in the Bahama Market. All the flavors, culture and traditions that this historic neighborhood represents come alive through the many streets.

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.

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.

Waterfront Playhouse Theater

Located on Mallory Square, the Waterfront Playhouse Theater is the oldest continuously running theatre group in Florida. For 65 years, the theater has brought laughter and entertainment to the residents and tourists of the Keys.

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 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.

White Street Pier

After taking a moment to view the moving AIDS Memorial, continue strolling towards the White Street Pier. It’s a favorite among locals, who refer to it as the unfinished road to Cuba. The pier is quite long and is where you’ll see friends hanging out, dog walkers and other Key West characters enjoying their paradise home.

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 sharks! 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.