Home USAFlorida A Weekend in Key West – The Best Things to Do in 2 to 3 Days

A Weekend in Key West – The Best Things to Do in 2 to 3 Days

by Valerie Vanr

A weekend visit to tropical Key West, Florida offers unforgettable experiences mixing history, culture, natural beauty with lots of fun!  Enjoy the city’s rich history where authors, artists and adventurers have all made their mark.

Whether you want to simply relax or get that adrenaline kick, Key West has it all!

Key West Itineraries

We have the perfect itinerary, no matter long you’re in Key West.

How Many Days in Key West?

Spend at least one full day in Key West.  Old Town’s historic area is relatively small.  Its highlights can easily be covered in one day.

Ideally stay a weekend (or even 3 days) enjoying the many museums, water activities and night life of this amazing city.

1 Day in Key West

2 Days in Key West
On a second day:

3 Days in Key West
With an additional day, enjoy any of these activities:

Map of Key West Attractions

Key West map with attractions marked labelled
Click on the map for an interactive map of the entire Florida Keys.

Key West Must-Sees

Be sure to enjoy these 5 things on your visit to Key West.

Key West Sunset Celebration

The nightly celebration in Mallory Square has been happening since the late 1960’s.  The civic square has an almost unobstructed view to the west of the Gulf of Mexico and has been known as “the” place to watch stunning Key West sunsets since the 19th century.

Cellphone screen showing sunset with scene behind
Mallory Square is known as the best place in Key West to see the sun set. Can you see why?

Every night, locals and tourists alike enjoy live entertainment by street performers of many different kinds.  Any evening you could find live music, magicians, jugglers, comedians, stunt performers with high-wire acts, sword swallowing and maybe even cats jumping through hoops.  There are always local artists with paintings, clothing, souvenirs and more. Of course, don’t forget to enjoy the food!

The festivities start about 2 hours before sunset and reach a fever pitch as the sun sets providing a breathtaking backdrop for the vibrant energy of this great street party.

Cat going through ring over cat on horizontal pole man cages behind
At the nightly Sunset Celebration, there are buskers performing everywhere sometimes with their feline friends.
Man tall unicycle juggling lit torches surrounded by crowd
As the evening gets darker, the buskers light their torches and the show just gets better.

By the way, any cruise ship docked during the day must leave port at least 2 hours before sunset.

Ernest Hemingway Home and Museum

Tour Hemingway’s Spanish Colonial home and the studio where the Nobel laureate wrote about 70% of his literary works.  Hear quirky stories about his life, travels, wives and the 6-toed cats.  Tour the gardens and see many supposed descendants of those original cats who still “own” the grounds.  Hemingway lived in the home between 1931 and 1939.  You many want to purchase a Hemingway novel in the bookstore.

For more information, see the Ernest Hemingway Home and Museum website.

Two storey house wrap around verandah both storeys lawn trees surround
The Hemingway home was built in 1851 and was updated by the Hemingways, including the addition of indoor plumbing.

HISTORY: The house, completed in 1851, is a US National Historic Landmark.  The Hemingways restored the neglected property and made several additions.  The house was one of the first in Key West to have interior plumbing and the huge in-ground swimming pool was the first in the Florida Keys.  Hemingway owned it until his sons sold it by auction after his suicide in 1961.  It opened as a museum in 1964.

Key West Museum of Art & History

Learn about Key West’s cultural heritage as well as local, national and maritime history over its two floors.  The ground floor houses temporary exhibits showcasing the museum’s vast collection of artwork and historic items on a rotating basis.  Upstairs photographs and artifacts explain the construction of the Overseas Railway, the 1935 hurricane that doomed it, the sinking of the USS Maine during the Spanish-American War, famous Key West residents and more.

This is the perfect place to get a better understanding of Key West’s uniqueness and the diverse influences that have shaped its history.

For more information, see the Key West Museum of Art & History website.

Three storey red-bricked building surrounded by palm trees
The Key West Art & History Museum is in the former US Custom House built in the late 19th century. Its architectural style is known as Richardsonian Romanesque. Many of the federal buildings in the US are constructed in this style. The district court and post office were also in this building.
Model of the USS Maine in clear exhibit case in museum
The museum exhibits cover many aspects of Key West history over the last 200 years.

HISTORY:  The beautiful, red-brick building, near the waterfront and Mallory Square, opened in 1891 housing the U.S. Custom House, the island’s Post Office and Federal Courthouse.  In the 1930s, the US Navy took over the building from the Federal government, converting it into office space.  It was abandoned in the early 1970s. The Key West Art & Historical Society realized its worth and, with lots of support from residents and government, the building was restored and re-opened in 1999.  The building is recognized as a National Landmark.

Key West Aquarium

See a wide variety of marine life in tanks of all sizes, both outdoors and indoors.  Tanks are filled with many different species, including sharks, stingrays, moray eels, barracuda, grouper, tropical fish, turtles, conch, sea cucumbers and more.

The aquarium is involved with marine conservation in the Florida Keys.  The Aquarium’s experts introduce some of the residents of the tanks, many of whom are at-risk species.  Learn about efforts to protect and conserve endangered species and others to eradicate non-native species from Florida waters.

For more information, see the Key West Aquarium website.

5 sharks in main fish tank Key West Aquarium
The main tank at the Key West Aquarium has some very large residents!
Black and white striped lionfish in aquarium
A lionfish has 18 venomous spines. If a spine pierces human skin and releases its venom, the reaction will be unpleasant but rarely fatal. It is rare for a human to be stung by a lionfish.

HISTORY:  The aquarium opened in 1935 after 2 years of construction. It was an open-air aquarium, one of the first in the US.  Unfortunately the 1935 Hurricane wiped out the Overseas Railway and the only land link to Key West 6 months after it opened.  This dramatically affected the number of tourists who could reach Key West and its initial success.  It persevered and survived.  In the 1960’s a roof was placed over the open-air tanks.

Harry S. Truman Little White House

Enjoy a guided, approximately hour-long, tour of the building used by President Harry S. Truman during his presidency as his “winter White House”.  Hear interesting stories about Truman’s time in Key West.  Learn how he, his wife and their staff, lived, worked and continued to govern while staying in officers’ quarters turned presidential residence.  President Truman visited Key West for rest and relaxation between 1946 and 1952, using the house for a total of 175 days. 

For more information, see the Harry S. Truman Little White House website.

Andy 2-storey white building surrounded by lawn
President Harry S. Truman spent 11 working vacations in Key West leading to the house being given the name the “Little White House”. It opened as a museum in 1991 and is still used by the government from time to time.
Black limousine with flag US
This Lincoln Cosmopolitan limousine is one of 9 that were used by Presient Truman when he traveled in the US. They were left in different locations around the country and available for his use whenever he was in the area. The VIP White Glove Tour offers visitors a ride in this limousine.

HISTORY:  The building was built on the waterfront in 1890 to house officers stationed at the U.S. naval base.  Eventually it was converted to house the base commandant and his family.  The house hosted a number of important guests in addition to Truman.  Thomas Edison, worked for the navy during WWI, Presidents William Howard Taft, Dwight Eisenhower, and John F. Kennedy all stayed during their presidencies. Presidents Jimmy Carter and Bill Clinton visited after their terms.  The house continued to be quarters for commanding officers until Truman Naval Station closed in 1974.  In 1991, it opened as a state historic site and museum.

Old Town Key West

Many of the city’s highlights are located in the Key West Historic District, essentially the part of the island west of White Street.  With only a day or two, spend your time in this charming area full of colorful houses, lively bars and vibrant shops.

The buildings are predominantly from the 18th to 20th centuries.  A number of museums are in these historic buildings helping preserve its architectural heritage.  The homes are built in “Bahama-style”; one or two-stories built to withstand high winds and most have wrap around porches to shelter windows from direct sunlight. 

Val bicycle Mallory Square 3 flags shelter in background
Beautiful Mallory Square is beside the cruise ship dock and where the very popular Sunset Celebration is held every evening.

Duval Street is the heart of Old Town’s commercial district.  A number of important Old Town buildings are on Duval or in the vicinity.  Full of souvenir shops, restaurants, bars and entertainment venues, Duval’s lively atmosphere is especially so after dark.  Every night is party night on Duval!

A trolley tour is a great introduction to the city and Old Town’s highlights.  If you want to leave the car behind, but don’t want to walk everywhere, consider renting a bike.  On our recent 3-day stay, we did both and it was the perfect mix for us.

More Old Town Attractions

Old Town Key West has many fantastic museums and attractions to explore.  These are worth a look depending on your time and interest.

Key West Lighthouse & Keeper’s Quarters

Climb the 88 steps at the Key West Lighthouse & Keeper’s Quarters for a bird’s-eye view of Key West.

Learn about the maritime history of Key West through the words and belongings of former lighthouse keepers and their families.  Discover the often difficult, now forgotten, life of the keepers.  They kept the light on regardless of the hazards to ensure the safety of ships and sailors.

left short building lighthouse center corner of keepers quarters right
The first lighthouse was built in 1825 at the shoreline. Unfortunately, the Havana Hurricane of 1846 washed it, and 14 people sheltering within, out to sea. That tragedy prompted this lighthouse to be built further inland on higher ground.

HISTORY:  This lighthouse opened in 1848 with a female keeper which was unusual for the 19th century.  Over the decades several upgrades occurred.  A new 3rd Order Fresnel Lens was installed; the tower’s height was increased; the Keeper’s Quarters were added; and the light was electrified.  In 1969 the lighthouse was decommissioned.  At that time, the Keeper’s Quarters housed a military museum and the tower was opened to the public for tours.  In the late 1980’s the structures were restored to their original designs and the museum re-opened in 1990 in its current configuration.

Tennessee Williams Museum

Explore the life and works of playwright Tennessee Williams at the Tennessee Williams Museum.  Williams, the winner of multiple literary awards, lived in Key West for more than 30 years.  The huge collection of photographs, plays, books, news articles, videos and other artifacts provide visitors with a deep look at Williams’ literary genius.

Tennessee Williams did not live in the museum building.  His first visit to Key West was in 1941 but he returned regularly often staying at La Concha Hotel (now the Crowne Plaza Key West).  He purchased 1431 Duncan Street in 1949 which was his home until he died in 1983.  His former home is not open to the public.

Room's corner covered framed pictures cardboard cutout Tennessee Williams
Tennessee Williams was one of a number of cultural icons who made Key West home. This museum, full of details about his life and works, opened in 2013.

HISTORY:  The museum building was built in 1884 on a spot which was the edge of the city at that time.  Over the next century, the city grew around it so that it is now in the centre of Old Town.  In recognition of Williams’ 100th birthday a temporary exhibit was held using 513 Truman.  Its success led to the comprehensive, permanent museum seen today which opened to the public in 2013.

Key West Shipwreck Museum

At the Key West Shipwreck Museum learn about the dangerous waters of the Florida Keys and the often life-saving role of “wreckers”.  The wrecking industry led to Key West being the most populated place in Florida and the richest, per capita, in the US during the last half of the 19th century.  Discover actual artifacts from the vessel Isaac Allerton, sunk in 1856 on a Florida Keys reef, which was rediscovered in 1985.  Climb the 65-foot observation tower to see Key West today and hear the story of the lookouts watching for ships in trouble.

Conch Tour Train in front of Shipwreck Museum Key West
At the Shipwreck Museum learn about the dangers of local waters and the lucrative wrecking industry. The museum is in the center of a busy part of Key West, near the Aquarium, Mallory Square and the Art & History Museum. It is the end of the Conch Tour Train route and the beginning of Old Town Trolley Tour. The Ghosts & Gravestones tour includes the museum on its route.

Mel Fisher Maritime Museum

Discover the secrets of the sea at the Mel Fisher Maritime Museum.  See artifacts and exhibits about maritime archaeology and the salvaging work of legendary treasure hunter Mel Fisher.  See some of the discoveries of Fisher and his crews from shipwrecks in the Florida Keys.  The museum was created by Fisher and became a non-profit organization in the early 1990s.

It is a museum, Conservation and Archaeology lab, and research facility.  The museum is open to the public 7 days a week with lab tours offered twice each weekday. 

HISTORY:  The building, built by the US Navy and completed in 1910, was used as a storehouse until the navy pulled out of Key West in the 1970s.  The government initially leased the building to Mel Fisher’s salvage company.  The company purchased it in the late 1980s.  After his death, the Mel Fisher Maritime Museum purchased it from the salvage company.

U.S. Coast Guard Cutter Ingram

Step aboard the U.S. Coast Guard Cutter Ingram, a Maritime Museum and National Historic Landmark.  Learn the history of the Ingram over her more than 50 years of service from 1936 to 1988.  She was stationed around the world carrying out search and rescue, drug interdiction, and maritime defense in both war and peacetime.  Tour the ship and discover what life on board offered.  Her exemplary record made her the ideal vessel to highlight the history of the US Coast Guard.  She is the most decorated vessel in the Coast Guard fleet and the only cutter awarded two Presidential Unit Citations. 

US Coast Guard Cutter Ingram docked Key West
The US Coast Guard Cutter Ingram is permanently docked at Truman Waterfront. It is a museum and memorial to the US Coast Guard.

HISTORY: After decommissioning, she was donated and displayed at the Patriots Point Maritime Museum in Charleston, South Carolina. In 2009 she was moved to her current dock on the Truman Waterfront.

Audubon House & Tropical Garden

Step into the past at the Audubon House & Tropical Garden.  The restored house is furnished with antiques from the first half of the 19th-century.  See orchids, bromeliads, tropical palms and more in the 1-acre garden as well as the outdoor cookhouse.  It is typical of early Key West cookhouses.  The gallery is a registered dealer of Audubon art and Audubon prints.

John James Audubon, a self-taught artist and ornithologist, is famous for his 19th-century drawings of the bird species of North America.  Local lore says that he visited the property during his Key West visit in 1832, and that the garden is pictured in several drawings of local bird species.

HISTORY:  The house was built between 1846 and 1849 for Captain John Huling Geiger, a harbor pilot, master wrecker and one of Key West’s wealthiest citizens.  It remained in the Geiger family for over 110 years.  It was restored and opened as the Audubon House Museum in 1960. 

Oldest House Museum

The Oldest House Museum showcases Key West and Southern Florida’s oldest house.  The former estate of wrecker Captain Francis B Watlington and his family includes their home, the kitchen house and an exhibit pavilion.  See family portraits, original furniture and the last surviving Southern Florida cookhouse.  Enjoy the peaceful garden at the rear of the house, away from the noise of Duval Street.

Andy in front Oldest House covered verandah 3 blue-shuttered windows above
This house, built in 1829, is older than the state of Florida. It was built when Florida was only a territory of the US, not gaining statehood for another 15 years.

HISTORY:  The house has stood at 322 Duval Street since the mid-1830’s.  The original structure, built in 1829, was smaller and located on Whitehead.  It was moved to Duval and expanded for Captain Watlington and his family whose descendants lived in the house until the 1970s.  It opened as a museum in 1975.

Key West Butterfly and Nature Conservatory

This glass-enclosed conservatory is a tropical wonderland, full of flowering plants and trees.  It is the perfect setting to see birds and butterflies from around the world.  There’s even a turtle or two.  The pair of flamingos are only too happy to put on a show.  At the learning center, see the displays about butterfly anatomy, life cycle, feeding and more.  Be sure to check for butterfly travelers when you leave the conservatory so that your only souvenir is from the gift shop.

For more information, see the Key West Butterfly and Nature Conservatory website.

Collage of birds and butterflies at Butterfly and Nature Conservatory
The feeding stations and perches were great places to watch both butterflies and birds.
2 flamingos in pool in tropical garden of Butterfly and Nature Conservancy
Rhett and Scarlett are Caribbean Flamingos. In the wild they live about 20 years but in captivity their lifespan is over 60 years. These two were each only 11 years old. Flamingos have been on the earth for at least 50 million years.

Fort Zachary Taylor Historic State Park

The state park is on the lands formerly Fort Zachary Taylor, the longest serving US Coastal Fortification.  Take a self-guided tour of the fort and then spend the afternoon enjoying its beautiful beach, snorkeling, fishing or paddling nearby.  Snorkeling equipment can be rented at the concession along with chairs and umbrellas.  Bikes are welcome in the park with dedicated lanes and lots of bike racks.

For more information, see the Fort Zachary Taylor Historic State Park website.

Val behind cannon many cannons behind
Excavations around Fort Zachary Taylor unearthed the largest collection of Civil War cannons in the US. Some have been returned to their proper places.
Val standing by rocks taking picture of boat in distance
These rocks are part of the rock jetty on the west side of Fort Zachary Taylor State Park. Fishing is allowed here along the Key West Shipping Channel.

HISTORY:  Construction of a 3-tiered fort began in 1845.  It was connected to Key West by a 1200 foot causeway.  The fort was a Union stronghold for the entire American Civil War.  During the Spanish-American War the fort was modernized, a new battery added and its overall height lowered.  The fort continued to be modernized and served during World Wars One and Two.  Its active duty ended in 1947.   Designated a National Historic Monument in 1973, it houses the largest collection of Civil War armament in the world.  The grounds and fort opened as a state park in 1985.

Southernmost Point in the Continental United States

The Southernmost Point Monument is a super-sized, colorful buoy at the corner of Whitehead and South Streets.  There always seems to be people in line for pictures but it moves quickly so don’t avoid stopping here!  The buoy notes that Cuba is only 90 miles away.

Val Andy beside multicoloured buoy noting southernmost point in continental us
Be sure to get a picture at the Southernmost Point monument.

Free Things To Do in Key West

The Southernmost Point monument is just one free attraction in Key West. There are many more places in the city to walk and explore.

For a complete list, see our article, 16 Best Free Things To Do in Key West.

Trees stony beach turquoise water

Beyond Old Town

While the bulk of the attractions in Key West are in Old Town, there are several outside the historic district that are worth a look if time permits.

Fort East Martello Museum

Discover the Fort East Martello Museum, a Civil War-era fort and citadel, restored to its 1860’s plans.  See artifacts from the Civil War and Key West’s military history, and learn about industries important to the development of Key West, wrecking and cigar-manufacturing.  The metal sculptures of local artist Stanley Papio are on display.  Robert the Doll is also a resident of the museum.

There are two ways to visit the museum.  Enjoy a self-guided daytime museum visit or come in the evening for the Ghost Hunt and Robert the Haunted Doll Experience. On the guided ghost hunt discover the stories of Civil War soldiers and the infamous Robert the Doll. 

HISTORY: Construction began on both East and West Fort Martellos during the Civil War.  While the Union was in control of the city, many citizens supported the Confederacy creating friction between the government and construction workers.  This animosity plus outbreaks of Yellow Fever and a hurricane led to many construction delays.  Ultimately, the forts were abandoned and never fully built.  Due to their strategic location they were used for storage, barracks and radio stations during the Spanish American War and both World Wars.  After WWII, they fell into disrepair and possession was given to the local county.  Fort East Martello opened as a museum in 1951.   Since then extensive restoration work has been done.

Val standing on pathway gardens palm tree building background
A shot in war was never fired from Fort East Martello nor were there any casualties caused by war.
Antique doll on chair with stuffed toy
Robert the Doll lives in the Fort East Martello Museum. We asked his permission before we took his picture. The consequences of not asking first don’t bear to be discussed.

Key West Tropical Forest & Botanical Garden

Enjoy the Key West Tropical Forest & Botanical Garden.  Started in 1936, this is the only frost-free, sub-tropical, native-plant, botanical garden in the continental United States.  The over 15 acres of garden and forest includes 2 freshwater ponds and has trails and wide boardwalks perfect for exploring.  See plants in bloom in spring and summer with plenty of birds and butterflies.  Many of the flora and fauna species are considered endangered.  Check out the visitor center, gift shop, plant nursery, sculptures of local artists and much more.

Dry Tortugas National Park

Dry Tortugas, about 70 miles west of Key West, is a great day trip.  Visit the 19th-century Fort Jefferson, one of the largest forts ever built.  It was never fully armed but was never attacked.  It served its intended role to protect the peace of a young country as part of a chain of coastal forts from Maine to California.  

The park is 100 square miles of open water with 7 small islands.  Its waters are known for the exceptional snorkeling and diving opportunities on coral reefs and shipwrecks.

Garden Key, the 2nd largest island in the park, is only about 14 acres.  It is the gateway to the park.  The park headquarters, visitor center, campgrounds and Fort Jefferson are all on Garden Key. 

How do I get to Dry Tortugas National Park?
The only ways to access Garden Key are by Key West Seaplane Charters, the Yankee Freedom Dry Tortugas Ferry from Key West (run by the Dry Tortugas concessionaire) or your own private boat.

For more information about park activities and camping, see the Dry Tortugas National Park website.

Key West Trolley Tours

A trolley tour is a great introduction to Key West history and its places of interest.  There are two options:  Old Town Trolley Tours (which we did) and the Conch Tour Train.

Old Town Trolley Tours

The “hop-on / hop-off” route covers the entire island in 90 minutes.  The trolley drivers are trained tour guides who recount the history and stories of Key West, in an entertaining, family-friendly way.  Learn about pirates, playwrights, presidents and much more.

Orange green trolley bus with door open
The “hop-on / hop-off” Old Town Trolley tours the entire island in 90 minutes. You can hop on and off at 13 different stops along the route.

There are 13 stops and riders can hop on and hop off as often as they wish all day long.  Stops are close to attractions, shopping, restaurants and lodging options so pick your stops based on the day’s itinerary.  The first tour leaves Mallory Square, at the front of the Aquarium at 10:00 am and the last one at 4:30pm.  Tours depart at least every 30 minutes. 

For the list of stops, price and to purchase tickets, see the Old Town Trolley Tours website.

Conch Tour Train

Sit back and enjoy a 75-minute tour through Old Town hearing the city’s legends and lore from the expert, friendly staff.  The tour has 3 stops.  Station Depot, 501 Front Street at Duval, is the beginning of the tour.  Grab your snacks in the shops nearby.  (The train stays here for 10 minutes.)

The second stop is Truval Village (around corner of Truman and Duval Streets).  Feel free to disembark, visit the nearby sites then catch a later train to continue the tour. 

Conch Tour Train of 4 cars with engine through treed neighbourhood
Since 1958, the Conch Tour Train has taken passengers on a 75-minute tour of Old Town Key West telling stories of the city’s most popular places.

The third stop is the Sails to Rails Museum, 901 Caroline St. between Grinnell and Margaret Streets.  End your tour at the museum or grab a later train back to Station Depot.

The first tour leaves Station Depot at 10:15 am and the last at 4:15 pm.  Tours depart at least every 30 minutes. 

For more information, see the Conch Tour Train website.

Ghosts & Gravestones Tour

For a great introduction to the city’s haunted history, and to take a load off your tired feet after a day of exploring, enjoy a 60-minute trolley ride instead of a walking ghost tour.

Costumed guides tell interesting stories about the spirits said to visit some of Key West’s historic locations, such as Captain Tony’s Saloon and Fort East Martello where a doll named Robert resides.  The tour visits the basement and first floors of the Shipwreck Museum for more paranormal stories of experiences in the building and details of a man’s suicide from the top of the building’s tower.  We had a great time being “the doomed” during our tour.

Man with white painted face on Ghosts & Gravestone Tour
Guides on the Ghosts & Gravestones Tour have lots of stories about their fellow spirits from Key West’s past.
Sign for Ghosts & Gravestones Tour
We were “the doomed” on our Ghosts & Gravestones tour.

The first tour leaves the Conch Tour Train’s Station Depot (501 Front Street at Duval) each evening at 7:00 pm and the last at 10:00 pm.  Tours depart every 30 minutes.  Reservations are required.

For more information and to book your tour, see the Ghosts & Gravestones of Key West website.

For a haunted walking tour, try the Key West Ghost & Mysteries Tour, a 90-minute walk to the most haunted locations for scary stories and experiences not to be forgotten.

Key West Bike Rentals

Old Town’s small size and the close proximity of attractions, makes two wheels the best way to get around Key West.  There are a several options in Old Town.  Most will deliver your rental to you during business hours.  We rented from A & M Rentals.

Andy bicycle road white building garden background
Tourists and locals alike use bikes to get around town easily. We enjoyed our day of touring with the bikes from A & M Rentals.
A & M Rentals513 South St. and 523 Truman Ave.
Eaton Bikes830 Eaton St.
EZ Riders Key West511 Truman Ave. and 105 Fitzpatrick St.
Island Bicycles929 Truman Ave.
Island Safari Rentals424 Greene St.
Key West Bicycles (by Fury)1200 Duval St.
We Cycle Key West326 Southard St. and 5160 US 1

Key West Bars with Live Music

Key West is known for its vibrant live music scene.  Some popular Key West bars often host talented musicians and bands, offering a variety of genres such as rock, reggae, blues, and country.

3 musicians performing on elevated stage with occupied tables and chairs in front
Sloppy Joe’s has been a local and tourist favorite since the early 1930’s, being a particular favorite of Ernest Hemingway. The bar’s been on Duval Street since 1937 when its patrons helped move everything from its original location down the block to its Duval home in one night without the knowledge of his landlord.
  • Sloppy Joe’s – This bar and restaurant, around since the 1930s, was Ernest Hemingway’s favorite hangout.  Enjoy their traditional Sloppy Joe’s sandwich and stay for the live bands on their massive stage.
  • Green Parrot Bar – Historic dive bar with friendly local patrons and eclectic live music including blues, rock, and reggae.
  • Irish Kevin’s – Lively Irish pub that encourages audience participation.
  • Hog’s Breath Saloon – Rustic outdoor bar, serving tropical drinks, with a variety of music genres.
  • Durty Harrys – Large outdoor party spot with great rock bands.
  • Captain Tony’s Saloon – oldest bar in Key West, the original location of Sloppy Joe’s and a favorite watering hole of Ernest Hemingway, Tennessee Williams, and Jimmy Buffet.

Key West Key Lime Pie

This is considered the official dessert of Florida.  Key limes, which are smaller and grown in tropical and subtropical regions, are more tart than regular limes, giving the pie its distinctive flavor. The dessert is typically made with a graham cracker crust and a creamy, tangy filling. Key West is particularly famous for its Key Lime Pie, and many establishments in the area claim to serve the best version of this beloved dessert.  

2 store employees behind store counter Key Lime Pie Company Key West
Key West is known for its Key Lime Pie. Watch it being baked at the Key West Key Lime Pie Company or take a class and learn how to make it like the pros.
Cream covered pie aluminum pie plate held above surface
Are you ready to search for the best Key Lime Pie? It’s hard work cause they are all so good!

These are some of the most popular places to sample Key Lime Pie:

  • Southernmost Key Lime Shop: Cute little shop with friendly staff.  We grabbed one of their tasty Key Lime Pies to go.  Sweet and tart.  Excellent.
  • Key Lime Pie Bakery: Fresh and tasty pies, variety of flavors and sizes, convenient location, fast service, good value for money.
  • Blue Heaven: This restaurant is famous for its Key Lime Pie.  This popular place also has live music in the evenings.
  • Kermit’s Key West Key Lime Shoppe: Lots of Key Lime Pie and other types of pies at this touristy shop.
  • Key West Key Lime Pie Co.: Pop into this shop to watch them make the pies on site. The crumbly crust of this pie is amazing.  Grab one to go.

Key West Beaches

Beaches are a major tourist draw, as visitors look forward to enjoying the crystal-clear waters of the Key West area.

These are the most popular beaches in Keys West.

Beach with swimmers in the turquoise water
The state park’s beach is a coral beach. Water shoes are recommended for your comfort.
Beach NameKnown for
Smathers BeachLong stretch of sandy shoreline with jet ski rentals.  Most popular.
Higgs BeachPicnic areas and a fishing pier.  Notable as the site of an 1800s African slave cemetery.
Fort Zachary Taylor Historic State Park BeachBlend of history and natural beauty.  Good snorkeling.
South BeachThis beautiful small public beach is located at the southern end of Duval Street.  Rent a chair from the resort.

Key West Sunset Cruises

One of Key West’s popular evening activities is watching the sunset over the ocean on board a beautiful sailboat.  Cruises may include live music, refreshing beverages, and light snacks.  Passengers relax and unwind enjoying the beauty of sunset on the tranquil waters of the Gulf of Mexico.  Many of the Key West charter companies offer sunset cruises. We used Danger Charters.

Val leaning on rail sailboat taking picture of sunset
We got some great sunset shots on Danger Charters’ Wind & Wine Sunset Cruise.

Key West Water Activities

A number of companies offer visitors to Key West the opportunity to explore the vibrant marine life and stunning coral reefs in the waters surrounding the island.  Snorkeling, jet ski tours, kayak rentals, dolphin tours are options with many of the Key West charter companies. We decided on a jet ski tour with Barefoot Billy’s Boat Cruises.

Key West Charter Tour Operators

These are several tour operators offering sunset cruises and water activities from marinas around Key West.

NameTours Offered
Danger ChartersSunset Cruises, Snorkeling/Kayaking Tours
Fury Water Adventures Key WestSunset Cruises, Dolphin Eco Watch, Jet Ski
Sebago WatersportsSunset Cruises, Snorkeling Jet Ski, Parasailing
Sunset Sail Key WestSunset Cruise aboard Patton’s Schooner
Barefoot Billy’s Boat CruisesJet Ski Tours, Dolphin watch and snorkel tour
Key West Eco ToursKayaking, Catamaran Sailing, Snorkeling Tours and Paddelboard Eco Tours
Sunset WatersportsSunset Cruises, Dolphin and Snorkel Tours
Capt. Hook’s Dive Key WestDiving and Snorkeling Tours
Andy jet ski waters around Key West
Andy enjoyed the Island Jet Ski Tour with Barefoot Billy’s!

Key West Festivals

There’s always something happening in Key West.  Here are some of Key West’s most popular annual festivals.

  • Key West Pridefest: A joyful and inclusive celebration of the LGBTQ+ community.  There are lots of parades and parties. (Early June)
  • Key Fantasy Fest: This adult-themed festival featuring elaborate colorful costumes has a wild party atmosphere and a great parade.  10-days of fun. (October)
  • Hemingway Days: A celebration of Ernest Hemingway’s legacy with literary competitions and of course, a Hemingway look-alike contest. (Late July)
  • Key West Songwriters Festival: A gathering of talented songwriters performing their original music across various venues in Key West. (Early May)
  • Key Lime Festival: A delicious celebration of Key West’s iconic Key Lime Pie.  There are pie-eating contests and cooking competitions. (1st weekend of July)

Key West Accommodations

Looking for a hotel in Key West?

Make Old Town your home base while exploring the Key West Historical District. Check out these great options.

Swimming pool surrounded by deck loungers
We had the pleasure of staying at The Gardens Hotel. The grounds include a tropical garden and a swimming pool with poolside bar. It is beautiful and less than a block from Duval Street.

Florida Keys Road Trip

Key West is just one of the many great locations in the Florida Keys.  Be sure to check out our detailed article, Florida Keys Road Trip, to discover many more places to visit on a one-week journey through the Keys.

Ribbon of highway surrounded by water and small urban areas
Florida Keys Road Trip – A Spectacular Drive from Miami to Key West

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Thanks to Florida Keys Tourism for hosting portions of our stay. See the Key West and the Florida Keys website for more Key West inspiration.