A Guide to the 30+ Best Things to do in Key West

Last Updated on 1st March 2024 by Sophie Nadeau

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A colourful and vibrant subtropical pocket of paradise, Key West is Florida’s most sunny destination. An oasis of green, with crystal clear coastlines and temperatures that will immediately make you sweat. Also the inspiration and beloved home of the writer Earnest Hemingway. This small and mighty island is definitely one to add to your bucket list!

Here’s your ultimate insider’s travel guide on the best things to do in Key West, as well as a brief history and top tips to get the best out of your trip.

Where is Key West?

Key West is an island city, part of the Florida Keys archipelago. It’s Florida’s southernmost point, although it’s lies closer to Cuba (however, you cannot see Cuba from the island) it’s considered to be part of the United States.

The island is only 4 miles long and 1 mile wide, with a population nearing to 27,000. However, a whopping 5 million people flock to this island annually!

What is Key West known for?

Home to serene beaches, pastel conch-style architecture and historic sites, Key West is a quirky pocket of life. There’s so much that has come from this small but mighty island!

Abundant with botanical beauty and fascinating wildlife thanks to its tropical climate. Key West is home to many animals of which are only found on the island, a lot of which are considered endangered species.

Being so close to Cuba, the island has strong ties with Cuban culture. Many Cuban people migrated to the island, including that of the skilled cigar-makers who quickly founded cigar factories.

Home and inspiration to the famous American writer Earnest Hemingway and his large family of polydactyl cats. It is also the island where the sweet dessert Key lime pie originated, and the delicious Papa Pilar’s rum.

Key West is also known for its lively nightlife culture, filled with plenty of spots to dance the night away!

How long do you need in Key West?

When visiting you should allow for at least one full day to explore the island. A day gave us the perfect amount of time to see all the main sight’s while still being able to sit down and enjoy a drink.

That being said, to enjoy the island city in a relaxed manner it’s definitely worth spending up to two or three days. There’s a lot to see and do, so you won’t be stuck for choice!

When is the best time of the year to visit Key West?

Between March-May, during the springtime season is the best time to visit Key West. The temperatures are bearable and the island isn’t too crowded, not to mention the vegetation and wildlife will be blossoming!

We visited in mid June and it wasn’t too busy. However, the weather was sweltering hot! The air was pretty stagnant with not even a single bit of breeze, so we ended up taking a shuttle around most of the island and had to drink a lot of water.

August through September are when the island is at its most humid and it’s also hurricane season, so you’d be best to avoid visiting during this time.

What is the climate of Key West?

A tropical paradise, Key West is situated within the subtropical region of the Western hemisphere. With warm streams of the Gulf of Mexico and the Gulf Stream flowing past, the Florida Keys have a mild tropical marine climate. This means that the average summer and winter temperatures rarely differ more than 10 degrees!

History of Key West

First and foremost, it’s thought that the island of Key West was home to several tribes of Native Americans (the Calusa and Tequesta tribes) as early as 800 CE. However, this all changed following European contact, with many of the people dying from disease or relocating to nearby Cuba.

The island remained mostly uninhabited until it was rediscovered by Spanish explorer, Juan Ponce de Leon in 1513. Originally naming it Los Martires, the martyrs, because he thought the island resembled men in distress.

Many of the early settlers in Key West were known to be wreckers. A life threatening work in which it was expected to venture out into dangerous conditions to salvage the goods from the ships that sank along the continental United States.

While a strict code of conduct mandated rescuing crews and passengers first, the wreckers still greatly profited from the salvaged cargo. So much so in fact that Key West became the richest city, per capita, in the United States thanks to its wrecking industry! High risks, but even higher rewards.

An important date in history to mark is March 30, 1886, when the Great Fire of Key West occurred, destroying a significant portion of the city.

Best things to do in Key West

Key West is abundant with things to do, we actually saw an impressive amount of the island and its attractions within the day. Here’s a list of some of the amazing things to do and see while visiting this paradise of an island!

Hemingway House

One of the highlights of the island and an absolute must-see (especially for cat lovers!) is that of Hemingway’s home. Earnest Hemingway and his wife Pauline moved to Key West in 1928 where they resided for eight years and had two children and a huge family of polydactyl cats.

Earnest Hemingway drew inspiration from Key West, in fact some of his best novels were written while relaxing either on the balcony of his residence or out on his boat, soaking up the island’s beauty.

Although the Hemingway’s moved on after, the house remained in their name until death. Today, it’s open to the public as a museum, stocked with an assortment of mementos that are linked to the life of the Nobel Prize-winning author. And for those wondering…yes, it’s still home to his cats too!

A particular highlight of the musuem (cats aside) is the outdoor swimming pool that’s located in the Hemingway’s garden. Built in 1938, this luxurious feature was the only one in the radius of 100 miles during the 1930s! Considered an architectural feat due to the sheer amount of labour it took to dig into the solid coral rock.

The museum is open daily from 9am-5pm and for a fee you can walk around the house and also see the cats, for a more in depth experience you can opt for a guided tour. Walk ins are welcomed, so you don’t need to reserve in advance. Find out more about ticket admission prices here.

Hemingway Cats

Hemingway was a cat person who adored feline friends and luckily for us, the Hemingway Cats still reside in the writer’s former palatial home to this day.

It all began with a gift a from a sea captain, a kitten with six toe beans was given to Earnest Hemingway and he named her Snow White.

A cat gifted with extra toes is said to be even better at catching mice (which is a blessing out at sea when you don’t want your stocks and supplies to dwindle from pesky pests). The polydactyl cats are not a specific breed, as in fact any cat can carry the DNA gene to produce kittens with six toes.

When you arrive at the Hemingway House there are quite literally cats everywhere! All of which are descendants of the original, Snow White. Following from how Earnest would name them himself, the cats are all named after famous people and characters.

Of course most people come to the museum to learn about Earnest Hemingway’s life, but thousands flock to this museum simply to see the world famous six-toed cats! There’s now even a Hemingway Cat App where avid fans can meet the current residences of the museum.

Key West Island Bookstore

Tucked away on Fleming Street, this independent bookstore specialises in local Key West and South Florida Authors. Key West Island Books is a quirky shop quite literally crammed full of books, upon entering you are filled with the familiar musty scent of stories and words scattered on pages.

Truly a book haven! It’s home to treasures by the greats and you could easily spend an hour or two hunting through the shelves finding all kinds of new, used and rare books!

Books and Books Key West

Another independent bookstore of the island is Books & Books. This gem of a bookstore was created by a small group of book-lovers, headed by the beloved author Judy Blume and her husband George Cooper.

The bookstore is locally owned and a non-profit business. With a collection of almost 5,000 titles it’s a literary paradise!

Admire the architecture

Key West has an eclectic mix of architecture thanks to the various cultures that have influenced it over the years. With over 3,000 wooden buildings dating from 1886 to 1912, they range from elegant mansions with wraparound balconies to cosy homes with covered front porches.

The main style of architecture found on the island is Conch houses. Characterised by large porches, wooden shutters and horizontal weatherboarding, the style is a blend of Victorian architecture with tropical sensibilities. Learn more in depth and take a guided Conch Train tour here.

Walking around you’ll quickly realise that no building on the island fades into the background; all unique and elaborate, their animated presence can be felt. The bright and vibrant colours of the buildings on the island reflect both its Caribbean and Cuban influences.

Less common, but still seen in Key West is that of the Mediterranean-style or Spanish Colonial. These buildings are usually painted white with red tiled roofs, made entirely from stone.

Because of its intense climate, almost all of the buildings on Key West have shutters and a porch. These features allow for the entrance of the sea breeze, while also protecting and providing necessary breaks from the sun.

The Oldest House & Garden in Key West

Having weathered hurricanes, fires and the harsh marine environment, the oldest house of Key West still stands. Located on Duval street, it was built in 1829 by a ship’s captain, Captain Francis B. Watlington.

Home to Watlington, his wife Emeline and their nine daughters for several decades. It’s made up of three buildings and a well maintained luscious green garden.

Today the house is a museum, welcoming visitors to view maritime artefacts, as well as salvaged gold, paintings and other treasures that were seized by the ship-wreckers. Visitors can wander through the furnishings and decor reflecting the era of the wreckers and their success.

For a small fee you can visit the house and gardens, which are open to the public daily from 10am-4pm. Walk ins are welcome so there’s no need to purchase a ticket in advance.

St Pauls’ Key West

Situated in the heart of the island lies the 19th century, Grand Episcopal church of Saint Paul. The magnificent white structure with brown shutters draws the attention to all those who pass by. The church we see today is a building which has been destroyed and rebuilt several times over…

Founded in 1832 by an official act of council, the original church was made of coral rock and ended up being entirely destroyed by a hurricane in October 11, 1846. The second church was built from wood, but burnt down in the Great Fire of Key West in March 1886.

Rebuilt once more, disaster struck again when the church was destroyed by another hurricane, October 11, 1909. Built again, but this time with flaws in the mixing of concrete wherein seawater had got in the mix causing the walls and columns to begin splitting.

To this day the church still has to undergo restoration work because parts of it are structurally unsound. However, despite its wobbly history, St Paul’s church is an iconic and historic community asset.

Open daily and free to visit, it’s definitely worth visiting this beloved gem of the residents of Key West!

Cornish Memorial Ame Zion Church

This sacred place of worship has a deep rooted history and is of great importance, named after Sandy Cornish, the church was founded for African-American residents of Key West.

Sandy Cornish was an African American farmer, businessperson, and civic leader of Key West. Formerly enslaved, he purchased his freedom but lost his papers so was recaptured, after an escape he publicly maimed himself so as to be deemed unable to work, preventing him from returning to slavery.

Cornish and his wife eventually moved to Key West where they set-up the Cornish Chapel of the African Methodist Episcopal Zion Church in 1864. It stands as the oldest African American church in South Florida.

Sandy Cornish passed away in 1869 at age 76 and was buried in the Key West cemetery, but the exact location of his grave was lost to history. In 2014 a plaque for Cornish was installed in the cemetery in his memory.

His inspiring legacy lives on, now known as the Cornish Memorial, the church continues to have services and stand as testament to the human freedom that Cornish fought so hard for.

Old City Hall Building

The Old City Hall remains to be an important landmark of Key West. Serving as the city government until 1965, it now houses the Key West Chambers of Commerce and visitors centre.

Situated on Greene Street, it was constructed in 1892, but what stands today is not the original building. Lost to the Great Fire of 1886, the city hall was rebuilt with red bricks that had to be transported to the island by boat.

The first floor initially housed indoor markets and then became home to the fire station, housing Key West’s fire engines. A highlight of the building is its four-sided clock tower that was erected in 1976.

Often passed by, the iconic red bricked building sits atop a granite staircase. This historical sit is definitely worth visiting, even if it’s just to stop by the staircase and watch the world pass by.

The Little White House

This historic building served as the vacation home for President Harry S. Truman during his presidency. In fact, it’s said that Truman spent a total of 175 day during his presidency in this little ‘winter White House’ on Key West.

Originally built in 1890 with the intended use of housing naval officers, over the years it has had many important visitors stay within its walls. To the likes of inventor Thomas Edison, scientist Edward Hayden and six other presidents.

But of course, the stand out guest is President Truman due to him serving as president during a critical period in American history. Today the Little White House stands as an important historic attraction showcasing the time and significance of the building during Truman’s time in office. 

The museum is open to the public daily from 9:30am-4:30pm and there are many different guided tour options you can take, including the White Glove Tour, where you can get the presidential treatment! Find out more about tours, tickets and how to visit the museum here.

Lighthouse Key West

Built in 1825 to safely guide ships through the dangerous reefs that surround the island, the Key West Lighthouse is an iconic landmark that stretches 65ft high into the sky.

With 15 lamps within 15 inch reflectors, the lighthouse could be seen from a far away distance and has withstood treacherous weather conditions over the years. In addition there are also the lighthouse keeper’s quarters where those who kept the lighthouse in operation lived.

Being a lighthouse keeper meant around-the-clock supervision of the facility, not to mention the upkeep of cleaning, maintaining and refilling the oil of 15 lamps. A memorable keeper of the Key West Lighthouse is Barbara Mabrity, who following her husband’s death kept the lighthouse for over 40 years. A woman as a keeper was nearly unheard of during the 19th century.

Today visitors can walk up the 88 steps of the lighthouse and discover the belongings, photographs and words of the previous keepers, as well as taking in the captivating views from the top.

Open to the public daily from 10am-5pm, I’d recommend purchasing a ticket online in advance as it’s cheaper! Find out more about ticket prices and visiting the lighthouse here.

The Old Schoolhouse

Also known as the Patterson Baldwine House, this historic building was erected in 1838 and moved location after the hurricane of 1846. It is believed to be one of the oldest building on Key West Island.

Located on the corner of Duval Street, the schoolhouse is a wooden structure with architectural elements of both Classical Revival and Bahamian. 

The residents Mr. and Mrs. William Pinkney lived in the small two storey home. William’s sister Madame Passaloque began conducting classes in the house, the very first of the island and she did so until 1860. Madame Passaloque was ahead of her time, considering that Florida’s public schools weren’t established until the 1870s.

You can’t actually visit the inside of this house, but there’s a plaque outside detailing its history and it’s situated nearby to the Oldest House Museum & Gardens Key West, so it’s worth stopping to take a look!

Shopping in Key West

A place that has something for everyone, from souvenirs, gifts, books and plenty more! Here are a few top spots for the ultimate shopping in Key West:

Duval Street

Lined with quirky places to pop into along this mile long street, it’s a popular location with a wide variety of shops that are filled with souvenirs and trinkets. It’s also home to some of the oldest buildings on the island, making it well worth a visit!

Clinton Square Market

Another popular place to shop is this mall which is located within an old brick building. Home to a wide variety of small boutique stalls selling homemade goods and local tasty delights, you’re sure to find more unique treasures here.

Mallory Square

The main square of Key West, abundant with restaurants, shops and hotels. It’s also the site of the famous Sunset Celebration, a nightly arts festival where visitors can explore local arts, craft exhibitors, street performers and local food carts selling delicious food- all as you watch the sun set!

The Key West Sponge Market

If you’re looking for a unique shopping experience, head over to this spot! While searching for the perfect sponge to elevate your bathing experience, you can visit the small museum located within the shop. The museum dives into the fascinating history of the sponging history that dates back from the 19th century.

The Southernmost Point Buoy

This anchored concrete buoy marks the southernmost point of the continent United States. To get a real feel for how close you are to Cuba (90 miles!) it’s an absolute must-see landmark to visit.

Located on the corner of South Street and Whitehead Street. This spot makes for a mesmerising place to enjoy sunrises and sunsets melting over the endless blue horizon that stretches before you.

The Cable Hut

Situated just next to the Southernmost Point Buoy lies another concrete structure, known as the Cable Hut. As the name suggests, its purpose was quite literally built to protect the connection between the land line and the 125 mile long underwater telegraph cable lines that link Key West and Havana, Cuba.

Key West Museum of Art and History

Situated just off of Mallory Square is Key West’s Art & History museum, an attraction open since 1891 welcoming visitors to admire centuries of art, history and people that have touched Key West.

The striking red brick building was actually initially home to the island’s customs office, postal service and district courts.

Nowadays, the building is home to a small museum set over two floors of exhibition space, it makes for the perfect place to spend for an hour or two. The museum is open daily from 10am-5pm and you can purchase your ticket on arrival.

Shipwreck Treasure Museum

Because of the islands strong ties with wreckers, and their importance in contributing to the wealth of Key West, this museum is not to be missed!

Step back in time to an era of Key West that was dominated by wreckers and see for yourself the very treasures they risked their lives for. This is very much an immersive and fun museum experience, involving role play, interactive elements as well as informative and interesting things to see on display.

A major highlight of the museum is the 594-tonne American merchant ship, Isaac Allerton which was discovered by divers of the museum in 1986. The huge ship sank in a hurricane just miles from Key West and is known for its sheer size and the vast number of gold and silver coins, as well as other artefacts on board.

It’s recommended to book in advance so you don’t miss out. Book your Shipwreck Treasure experience here.

Fort East Martello Museum & Gardens

A historic site that features exhibitions of local art and history, the museum is situated within a US Army Civil War Fort and tower.

The museum displays various exhibits of local art, history and culture. With specific focuses on the the island’s early settlers, maritime heritage, sponging, fishing, military involvement and its Cuban influences.

Also notably, the museum is home to the infamous Robert (doll) who is allegedly haunted…previously owned by the author, painter and Key West resident, Robert Eugene Otto.

Open daily from 10am-5pm, it’s well worth a visit for a more in depth insight of Key West and how it has become the place that it is now.

The William Curry Warehouse

Key West businessman and entrepreneur William Curry was the first millionaire of Florida! Curry lived on the island during the ‘golden age’ of wrecking and this historic building is where he stored the salvaged goods, as well as using it as a spot to host auctions.

For those business minded, you may want to stop by the warehouse to take in a sight where big bucs were made!

US Coastguard Headquarters Key West

The most southernly coast guard station in Florida, this historic site was originally located on the waterfront just off of Mallory Square. As the name suggests, its of great importance in maintaining the coastal patrol as well as maritime law enforcement.

Papa’s Pilar Rum

Sample the rum that’s made in tribute to writer Earnest Hemingway and named after his boat Pilar. We visited Papa Pilar’s distillery and got to try some of the sweetest and smoothest rum!

Thanks to the warm tropical temperatures there is an abundance of sugarcane, which is a crucial ingredient in making tasty rum. This alcoholic spirit is deeply rooted in maritime culture, this is because sailors were often given a provisional ‘Rum Ration’ on board their ships.

On the tour we were shown around by an expert guide who took us through the distillation and production processes, showing us how the caramel golden liquid is made.

Afterwards you can taste some of the delicious rum for yourself, as well as explore a small exhibit of photographs that chronicle the history of Hemingway, rum production on the island and how the distillery came about.

Be aware, the drinking age in the United States is 21 and over, so you can only drink some if you are of legal age. Book your rum experience online in advance through Papa Pilar’s official website.

Head to the beach

Formerly a string of coral reefs lay below the water, so much of the shoreline of Key West is rocky or used for docking boats. However, there are a number of beautiful beaches that make for the perfect spot to soak up the sunshine. And trust me, the tropical climate will have you itching to take a dip in the water!

Here are just a few top suggestions:

Fort Zachary Taylor Beach

Located within a state park, this beach boasts of beautiful crystal clear, warm waters and a huge stretch of white plush sand. Because of the clarity of the water, it also makes for an idyllic spot to go snorkelling!

Straw Hat Beach

A little off the beaten track, Straw Hat beach is one of the more secluded spots. Its white sand, clear waters and relaxed atmosphere give it a Caribbean vibe.

South Beach

A hidden gem of the island, this is probably one of the smallest beaches. Located at the southern end of Duval Street, it’s the perfect place to take a dip after exploring some of the oldest historic buildings of Key West.

Smathers Beach

Almost half a mile long, this is the biggest of the beaches on Key West. Easily the most popular thanks to its prime location, the beach is easily walkable from the city centre. Boasting of volley ball courts, food trucks and lots of amenities close by.

Dog Beach

If you happen to be visiting with your furry companion you’ll want to visit this beach as it’s the only beach in Key West that allows to go unleashed. It’s possibly just a spot for dog owners due to it being small and rocky, but well worth a trip for your furry friend to play in the sand and take a dip!

Sloppy Joe’s

Open since 1933, Sloppy Joe’s boasts of offering the ultimate party experience! A bar with live music, dancing and even a separate tap room for those who love to watch sports.

This famous and beloved saloon was apparently often frequented by Earnest Hemingway, known to be his favourite place to drink and relax during his time on the island.

During the day Sloppy Joe’s is a sleepy bar you can enjoy a refreshing pint in and take respite from the sun. By night, it turns to a place where locals and visitors can let loose and dance into the early hours of the morning!

There’s quite a detailed history of Sloppy Joe’s detailed on their official website. Learn more about the history, as well as up coming live music and events here.

Green Parrot Bar

Another iconic and firmly established drinking spot of Key West is that of the Green Parrot Bar.

This beloved bar has seen plenty over the past 100 years and it remains to be another classic spot of the island that comes to life at night thanks to its live music scene. A charming dive bar full of character!

If you are really fascinated by this bar, the Green Parrot (weirdly) show a live webcam view of the bar on their website, apparently so people don’t miss out on the fantastic live music thats shown there. See the official Green Parrot Bar site here.

Eat Mattheessen’s Homemade cookies

You won’t be able to walk past Mattheessen’s as the scent of homemade cookies is sure to draw you in. Deliciously soft, warm and mouthwatering, they are quite literally everything you want from a cookie!

Mattheessen’s Homemade is a family-owned dessert parlour that can now be found in three different locations on Key West, one of which is on the famous historic Duval Street. Priding themselves on quality ingredients and creating the tastiest of treats, you’ll want to sample one of their many baked goods.

Sample Conch Fritters

A delicacy commonly served in the Bahamas and Florida Keys, this deep fried fritter is commonly served with key lime mustard.

A conch is in fact a sea snail, housed in a shell of superior strength which is often used as a musical instrument or as decoration. Conch has been widely consumed for years and the favoured way to eat it is in fritter form!

Perfect as a mid afternoon snack, experience Key West through tasting this local island treat.

Getting around Key West

Walking around Key West

Walking around Key West is fairly easy, it’s essentially all flat. The only thing that’s likely to obstruct you from doing so is the intense heat conditions (and how humid it can get out).

Old Town Trolley Tours

A great way to ensure you see all of the island’s Old Town, as well as avoiding heatstroke, is by popping on one of the trolley tours!

It’s a great way to experience Key West and you can do so at your own pace as it’s a hop-on hop-off trolley bus tour. Consisting of 13 different stops, the driver offers a guided tour as you go around, and you can get off as you please, discovering over 100 different historic sites. Book your Old Town trolley tour here.

Key West Conch Train Tour

Another excellent hop on and hop off tour is the tourist train, taking you to all the historic and major sight-seeing spots of the island. Hear about the legendary stories and people of this tropical paradise and explore the various attractions at your own pace.

I would definitely recommend this tour or something similar, especially if you are only visiting Key West for the day. Book your Conch Train tour here.

Taxis in Key West

Easily found in front of hotels and the major attractions, there’s no shortage of taxis on Key West. While this is more expensive that other available options, it can make for a convenient mode of transport when hopping around the island (especially if you happen to be partying into the early hours of the morning).

How to get to Key West

The fastest and easiest way to get to Key West is flying there. Yes, believe it or not this tiny island has its very own airport! Serving major airlines such as American Airlines, Delta Airlines and Silver Airways.

However, the island is also connected to the mainland Florida by an impressive amount of 42 bridges. Aptly named the Seven Mile Bridge, this 113 mile stretch of concrete means you can drive to the city island. The distance from Miami is approximately 160 miles, this takes around 3-4 hours.

As we were staying in Miami, we decided to take take a guided coach tour to the island. We met in Downtown Miami in the early hours of the morning at 7:30am and returned to the city at around 9:30pm.

The tour was excellent and I definitely recommend it! (but be sure to bring lots of water and maybe even a hand held fan if travelling during the peak of heat). Offering scenic views along the drive, while an expert guide gives more insight to Key West and its history. Once on the island you are given 6 hours to do as you please! Find out more about booking a day trip to Key West from Miami here.

Where to stay in Key West

This subtropical paradise is sought after and as such for the most part it can be very expensive on the island (also to note, a lot of the hotels on the island are adults-only).Here are a couple suggestions of where to stay:

Simonton Court Hotel Key West: Located in the Old Town, this adults-only hotel offers continental breakfast served by the pool…and there are 4 pools in total! A boutique bed & breakfast, this historic inn starts at prices of £383 per night. Check for more prices and availability here.

The Conch House: Set within a classic Victorian-era 19th century home, this luxurious hotel is just a 3 minute walk from Duval street and 6 minutes from Hemingway’s house. The rooms are bright and charming, decorated in an antique style. But again, it’s very expensive to stay here. Check for more prices and availability here.

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