Key West in Florida: best things to do in Hemingway’s island

Famous all over the world for its beautiful sunsets, Key West boasts an impressive amount of attractions in relation to its small size and visiting it without missing anything is a feat, especially if you intend to devote only 1 day to it. Moreover, its vitality makes the task even more difficult: it’s hard to walk down Duval Street and its surroundings without stopping every time to look at a store window, enter a store or be charmed by the many musicians who perform in the clubs from early afternoon.

In this article, we will therefore try to discover not just the main places of interest in Key West, including its beaches, Hemingway‘s house, its naturalistic “oasis” and the best activities, but also to understand how to organize a visit that fully exploits all the potential of this amazing island at the edge of the States.

Information and curiosities about the Conch Republic

If there is a place that doesn’t lack personality, it is Key West, whose vitality and “anarchic” attitude can almost be felt in the air. Here you will find a lot of hospitality, the desire to stop for a chat and have fun together, but also the desire to stand out. The history of Key West, the Conch Republic, is quite eloquent in this regard: originally it was a den of pirates, who ran riot until the annexation of Florida to the United States.

Later, the numerous ships that crashed on the reef gave rise to the business of wrecking, the recovery of memorabilia and valuables from sunken ships, a practice that made many Key West residents rich until the construction of lighthouses solved the problem of ship orientation at sea. Other businesses coming from the sea, such as sea turtles and sponges, then became important resources for the island, together with the production of cigars, which was established mainly thanks to Cuban immigration.

The signs of all these historical moments are still very evident in Key West and walking along its streets is a bit like taking a leap back in time, retracing the many phases, even the dramatic ones, that this island has gone through. But perhaps nothing explains the spirit of this extravagant town more than the founding of the Conch Republic.

In April 1982, the U.S. government set up a blockade on the border with the Keys, whose inhabitants were suspected of illegally bringing in Cuban refugees and trafficking drugs. On the 23rd of the same month, the mayor declared secession from the United States, declaring war on Washington and forming the Conch Republic.

The symbolic act was to break some Cuban dry bread on the head of a man in uniform, surrender exactly one minute later and then ask for war reparations of one billion dollars. It was obviously a publicity stunt (which was also replicated in 1995, when a “naval assault” was organized aboard the historic ship Western Union, from where water balloons, conch fritters, a typical dish of the island- and pieces of Cuban bread were launched), but it is a good explanation of Key West inhabitants’ rebellious spirit, who since that day have earned the right to be called Conch and to celebrate the Conch Republic Independence Celebration every year, which is basically a good excuse to party.

Key West: where is it located and how to get there from Miami

Key West is part of the Florida Keys (or simply Keys), an archipelago that stretches from the continental end of the United States to the Gulf of Mexico over 100 miles. This strip of tiny islands of white coral sand, a paradise for snorkeling and diving, begins to develop 15 miles southwest of Miami and ends right in Key West, the southernmost point of the continental United States, just 95 miles from Cuba.

Usually, Key West and its “sisters” can be reached via Miami International Airport (2100 NW 42nd Ave.), and perhaps a visit to the Keys can be combined with a stay in the metropolis or with a more complete Florida trip (Everglades park included). KeyWest actually has its own airport (3491 S. Roosevelt Blvd.), which is named as being international but is actually domestic.

There are also several cruise lines that call at the Mallory Square docks, and even Greyhound company buses that leave from Miami, but the best thrill is to reach the island on a road trip along the Overseas Highway, the scenic route that crosses the islands of Key Largo, Islamorada and Marathon (just to name a few), a sort of long 126-mile “bridge” over the water between the Atlantic Ocean and the Gulf of Mexico.

To reach the Keys by car from Miami, you have to cross Homestead (where Coral Castle is located), Florida City and drive along Everglades National Park. If you prefer to opt for an organized tour, take a look at our article on tours from Miami to Key West.

How to get around, orientate yourself and how many days to take visiting

Before detailing the many attractions that the city has to offer, it is important to have the basic coordinates to orient them geographically. The most interesting area of Key West is the so-called Old Town, a picturesque village with a fishing vocation, made up of alleys and wooden houses, many in different colors and full of historic residences. Although the area can be visited entirely on foot, it is larger than it may seem, so do not underestimate it.

The most interesting part of Old Town is the one that unfolds between the streets of Duval Street and Whitehead Street, which almost seem to be “competing” for who can show off the best attraction. At the south and north ends of the two streets are two authentic symbols of Key West: Southernmost Point and Mallory Square (a few steps from the historic port).

Outside this area there are interesting areas within walking distance: West, towards the sea:

• Truman Annex, home to the Little White House, the US Coast Cutter museum ship, Fort Zachary and the Florida Keys Eco-Discovery Center

To the east, towards the interior:

• The cemetery area, which is technically always part of Old Town and includes such places of interest as the Basilica of Saint Mary Star of the Sea and – abutting the Meadows neighborhood – the city’s Bayview Park, with its beautiful memorial dedicated to veterans.

It’s impossible to visit all of these areas in one day, so if you want to “get your fill of Key West” dedicate at least 2 days to it, and personally I’m pretty sure that even with 3 days you’d have little chance of getting bored. If you only have 1 day available, focus your attention on Old Town, integrating it with a detour to one of the 2 bordering areas listed above.

You will probably arrive by car, but you don’t need a car to visit most of Key West. You can visit the town on foot or even by bike (you’ll find many bike rentals on the island) or, alternatively, you can opt for the Old Town Trolley Tours (location: 1 Whitehead St.) that allows you to visit the historical part of the city hopping on and off at will. The ticket is valid for one day and costs about thirty dollars, with the possibility of a discount if you buy online.

What to see in Key West Old Town

In Old Town, every building, even the smallest, seems to have something interesting to reveal, so it’s hard to resist the temptation to browse through historic houses, museums, stores and restaurants in search of the most curious and surprising detail; the impression you get is that of a small open-air museum. I have divided the various areas of Old Town into zones for convenience and the visit is conceived as an itinerary, from South to North. You can easily follow it by referring to the points included on the interactive map above.

From Southernmost Point to Gato Village

Main Attractions:

• Southernmost Point
• Key West Butterfly & Nature Conservatory

The main landmark in this area is the famous Southernmost Point, the colorful buoy-shaped monument marking the southernmost point in the continental United States that you’ll find at the end of Whitehead Street. This beautiful concrete pylon (which marks the beginning of our itinerary) was erected in 1983 and has become so famous that you’ll have to wait in line to take a picture of it undisturbed.

You might be interested to know that the nearby Fort Zachary area is actually located further south than the famous buoy, so if you want to be able to say that you’ve been further south than Southernmost Point, pop over to Fort Zachary Beach (which we told you about in our guide to the best beaches in Key West).

Near the buoy-shaped monument you will find other 2 elements of interest: the statue in honor of the preacher Albert Kee, who sold fish right in this area, as well as blowing into a shell as tourists passed (the pose in which the statue still portrays him) and the small telegraph station (Telegraph Cable Hut), which played an important role in the realization of the first call between the United States and Cuba.

After having taken a selfie at SouthernMost Point, it’s time to find out which is the SouthernMost House; yes, in this area the inhabitants are competing on who can boast the title of the most southern house in the United States (I have seen at least 2 that boasted this record). The “official” one is the Cayo Hueso House (where you can also stay overnight, as we explained in our guide on where to stay in Key West), which stands out for its magnificence and magniloquence.

To reach it, just turn onto South Street and go to the intersection with Duval Street, it will be hard for you not to notice it. A few feet further on South Street you will find another historic building, the house that belonged to the important philosopher and educator John Dewey, now converted into the Bed & Breakfast establishment La Mer & Dewey House. Also a few steps away, in the direction of the sea, you will find the small South Beach.

Now start walking up Duval Street, the most stimulating street full of attractions in all of Key West. The first possible stop is already noteworthy: it is the Key West Butterfly & Nature Conservatory (1316 Duval St.), a sort of tropical paradise where you can admire fancifully colored butterflies, exotic plants, pink flamingos and other birds with colorful plumage (it is open every day from 9 am to 5:30 pm).

After a few blocks, on the right, at Catherine Street, you will come across two interesting historical buildings. The first, which today houses the hotel/restaurant/cabaret LaTeDa, is known as La Terrazza de Marti for the famous speech that Cuban revolutionary Jose Marti gave in 1883 from the balcony of this building; the second, 2 buildings further on, was the speakeasy (a place where alcohol was illegally traded during the Prohibition) of the famous rum producer Raul Vasquez. In keeping with the past, here you’ll find the Rhum Bar, a bustling establishment with a wide selection of spirits, and one of the best places in Key West to have a nightcap.

At this point you can continue up Duval Street towards the more lively area of Old Town but, if you are irrepressibly curious, take a short detour to discover a small historic corner of Key West: Gato Village, also known as Gatoville or Barrio Gato. In the 1880s, cigar trader Eduardo Gato built a real village near his factory with a bakery, laundry, billiard room, stores and ice cream parlor, all in order to attract qualified personnel to his company.

Today there are two testimonies of this: the factory itself (Gato Cigar Factory Museum), at the intersection of Amelia and Simonton Street, and Gato Village Pocket Park, a small green space that hosts the reconstruction of the facade of a cottage for the production of cigars of the time, and a sculpture that seems to be the largest cigar in the world.

Hemingway’s house, the lighthouse and Bahama Village

Main attractions:

• Ernest Hemingway House
• Key West Lighthouse
• Blue Heaven

Get back on Duval Street and keep going north; after crossing Truman Avenue, you will find yourself in an area of a few blocks that is a real concentration of places of interest. There are 3 museums in the vicinity of Duval Street and Whitehead Street, and just a few steps away is Bahama Village, so called because of the high concentration of Bahamian immigrants who settled there in the 1800s.

The first museum, the Tennessee Williams Exhibit (513 Truman Avenue), will be of particular interest to theater buffs: a pastel yellow house houses a collection of photographs, plays, first editions, newspaper excerpts, rare magazine articles and videos dedicated to Tennessee Williams, an important playwright known for works such as A Streetcar Named Desire and A Cat on a Hot Tin Roof, who lived in Key West for over 30 years. Among the collection’s top items you’ll also find his typewriter.

Take Duval Street again and turn left onto Olivia Street, where 2 of Key West’s most iconic attractions await you: Key West Light House and Keeper’s Quarters Museum and the Ernest Hemingway Home and Museum.

The villa, which was inhabited by the great writer from 1931 to 1939, is now open to visits for a fee (bring cash) and, as in the beginning, is literally invaded by cats, which, among other things, are the true descendants of those with 6/7 fingers that the man of letters loved to take care of in his garden. The building dates back to 1851 and over time has proven remarkably resilient to the elements: during Hurricane Irma in 2017, when the entire island was evacuated, the museum’s curator, employees (and the many cats with them) refused to leave the house, and all survived without any problems.

The house is well preserved and you can freely explore it by visiting all the rooms, including the outhouse where he wrote The Snows of Kilimanjaro and The Short Happy Life of Francis Macomber, the pool, the garden and, of course, the cat cemetery, with the name of each one engraved on the headstones.

Right in front of Hemingway’s house is another fine Key West museum, dedicated to the lighthouse and keeper’s house. The construction of a lighthouse on the island became necessary in 1823, following the installation of a U.S. Naval base, and was erected 2 years later, although it did not have an easy life: it was destroyed by a tornado and, after reconstruction, underwent further interventions, but the most interesting story to learn concerns the keeper Barbara Mabrity, who played the role of guardian for over 30 years, losing many of her family members here too.

In addition to the possibility of climbing the 88 steps necessary to reach the top of the lighthouse and thus enjoy a panoramic view of the town and the sea, the visit to the site is an interesting opportunity to learn about a piece of Key West’s history and to identify with the lifestyle of the time, especially with that of the lighthouse keepers, whose house and interiors have been meticulously reconstructed.

Now continue along Whitehead Street in a northerly direction and after one block, at the intersection with Petronia Street, you will notice some curious stores, such as The Coast, with its very particular concept, or Crystals and Coconuts, with its unique internal garden of trinkets. You will also see the sign for Bahama Village Market, which will announce that you have arrived in Key West’s famous Bahama Village, even though the actual sign for the entrance to the neighborhood is one block away, at the intersection of Petronia and Duval Street.

Even if this market will attract your attention, desist; in this small agglomeration of 2 streets called a bit pretentiously “village” there is even better: I’m talking about the Blue Heaven (729 Thomas Street, but you can enter from Petronia Street to wander freely in the outer space). The history of this place is that of a first-class dive bar: there used to be a brothel here, later replaced by boxing matches refereed by Hemingway himself, and now it’s probably the best place to go in Key West: great atmosphere, live local music, excellent food, many roosters wandering among the tables… personally, this place has been addictive (maybe it was their fabulous Key Lime Pie?).

Upon exiting Blue Heaven, take Petronia Street again to arrive at the intersection with Duval Street, where you will see the sign welcoming you to Bahama Village. The more observant among you will notice the rainbow stripes at the intersection, the unmistakable sign that you are in the epicenter of gay-friendly Key West, as evidenced by the presence of the Gay Key West Visitors Center 2 blocks away.

The Heart of Duval Street: Hunting for Historic Buildings and Social Life

Top Attractions:

• Curry Mansion
• Capt Tony’s Saloon
• Lots of live music

Are you ready to enter the most vital yet history-rich soul of Key West? In the many historic buildings you’ll encounter along this stretch of Duval Street, a good portion of the city’s history (and more) has been written: within the walls of these homes Florida’s first successful entrepreneurs lived, important political figures (including 2 U.S. presidents) were hosted, and great writers composed their literary masterpieces. But you won’t see only history, because from here on Key West gives its best also from the point of view of clubs and entertainment.

Arriving at the intersection with Southard Street, the temptation for a detour will immediately arise: turning left, in fact, you will have the opportunity to drop by the Green Parrot Bar (at the intersection with the usual Whitehead St.), a real institution opened in Key West in 1890 and that throughout its glorious history has hosted events of all kinds, from tattoo contests to celebrations of birthdays for pets. It is also a great place to listen to live music and, even if you happen to be there when there are no particular events, it is still worth taking a tour inside to enjoy its special atmosphere and admire the large collection of guitars, some signed by great guitarists.

Returning to Duval Street, after a few yards, you cannot help but notice one of the historical icons of the famous street of Key West to your right: the imposing facade of the Strand, a theater built in the early ’20s now abandoned. It’s not worth going inside, unless you want to buy something from Wallgreens who took over the building, but the facade of the old theater is worth a photo at the very least.

Right next door you’ll notice Willie T‘s, and it’s not just the singer on duty that will catch your attention: here the ceiling is entirely covered with dollars (yeah, just like at No Name in Big Pine Key, which we talked about in our guide to the Florida Keys) and as we’ll see in a moment there is also another place that can boast this peculiar feature.

In the same block you will also notice a beautiful Hispanic historic building: the San Carlos Institute, built in 1871, soon became the cradle of the Cuban independence movement led by José Martí, who renamed it “La Casa Cuba”. Inside you’ll find an interesting museum, a library, an art gallery, a theater and even a school.

After a few steps, another possible detour towards Whitehead Street comes up again. At the intersection of Whitehead Street and Fleming Street, the Mile Marker 0 is waiting for you, marking the end of the Overseas Highway (or Route 1). It may not be as famous as the sign at the end of Route 66, but a photo is a must. Just 2 steps further, continuing on Whitehead southbound, you will notice the Monroe County Courthouse, the beautiful county courthouse dating back to 1915.

Head back to Duval Street again and get ready for a real feast of historic buildings, they’re all within the next 2 blocks:

• La Concha Hotel: an important hotel active since 1926 where Tennessee Williams wrote A Streetcar Named Desire
• St. Paul’s Episcopal Church: erected in 1912, after the previous 3 were destroyed by fire and hurricanes. It is the oldest diocese in Florida.
• The Oldest Schoolhouse: also known as the Patterson-Baldwin House, this 1847 building is one of the oldest on the island; Madame Passaloque was way ahead of her time here, starting her school well before the Florida school system was organized in the 1870s.
• Oldest House & Garden Museum: Key West’s oldest house, built in 1829 by Richard Cussans and able to withstand fires, hurricanes and floods. You can visit it and discover how the family of Captain Watlington and his wife Emeline lived, who raised 9 daughters within these walls.
• Key West Woman’s Club: A stately home built in 1892, where Captain Martin Hellings, director of the International Ocean Telegraph Company, and Eleanor, the daughter of William Curry, known as Florida’s first millionaire, lived. The building was bought in 1940 by the Woman’s Club and now houses the Red Barn Theater.
• Dr. Joseph Yates Porter House: among the finest historic mansions in Key West (built in 1892), it is also known for being the home of Florida’s first health officer, whose efforts were instrumental in discovering the causes of yellow fever.
• Fogarty Mansion: 1887 home of Joseph Norman Fogarty, who served as mayor of Key West. Prominent figures were received within these walls, such as Henry Flagler, visionary creator of the Overseas Highway, and 2 Presidents of the United States: William Howard Taft and Grover Cleveland.

If this little full immersion into the past of Key West was not enough for you, all you need is a small detour on Rose Lane to find an authentic piece of history, Casa Antigua (Trev-Mor Hotel), the famous hotel built in 1919 to withstand any disturbance, made with bricks taken from the nearby Fort Zachary. What made it famous, however, were not its architectural principles but the fact that, during his stay, Ernest Hemingway wrote his masterpiece Farewell to Arms. Unfortunately, the structure is currently closed and you can’t visit the inside (but you can always take a picture of the weirdest memorial plaque in Key West, see image below).

To return to Duval Street, take Caroline Street and turn onto Ann Street, where 2 more fascinating historical landmarks await you: the Curry Mansion and the Old City Hall. While for the latter you will have to be satisfied with a simple view from the outside, the residence of Curry, Florida’s first millionaire, can be visited for free and can give you a few pleasant minutes to discover an old mansion of the late nineteenth century full of antiques, including the piano by Henry James and the chandelier by Frank Lloyd Wright. On the top floor you can “climb” up to the roof for a view of the Old Town buildings (it seems that from this position sailors’ wives waited for the return of their husbands from their sea voyages).

The remaining area of Duval Street is mostly full of clubs and entertainment, but even here history does not leave us, as some of these, as we shall see, have indelibly marked Key West.

At the corner of Duval and Caroline Street it is really hard not to notice The Bull & The Whistle, with its wrought iron balcony that reminds us a bit of the bar on Bourbon Street in New Orleans. In fact, this building is as if it housed 3 of them at once: on the ground floor there is The Bull, the typical place to party where local musicians perform, with its walls decorated with murals depicting events and important people in the history of the island; on the second floor there is The Whistle, a more intimate bar with pool tables and the possibility of accessing the wrought iron balcony; finally, on the roof, the Garden of Eden, a bar that can boast a very unusual feature: clothes are in fact optional!

At the next intersection, the one with Greene Street, get ready for another taste of history. Sloppy Joe’s Bar, with its large sign, is not just another place where local artists perform and islanders gather to party; this bar can in fact boast a respectable history and, above all, a client of considerable caliber: Ernest Hemingway, whose birthday is celebrated every year with the Hemingway® Look-Alike Contest, a competition where patrons compete to see who looks more like the great writer.

Many people don’t know, however, that the original location of Sloppy Joe ‘s is just a few feet away at what is now Capt Tony’s Saloon (on Greene Street), another example of ceiling wallpaper made from dollars, car license plates and…. bras! The atmosphere (which I personally found more charming than Sloppy Joe’s) is that of an underground dive bar, with the inevitable live music and a few pool tables.

Along the main street there are 2 other places that deserve a mention: the first, the Smallest Bar in Key West, which as the name suggests boasts of being the smallest bar on the island (with an adjoining B & B that we told you about in our guide on where to sleep in Key West), while the second, Hog’s Breath Saloon, is a fixed stop for Duval Street Crawlers (so the patrons who love to wander from bar to bar to party, one of the most popular activities of all Key West, are known). You won’t see its distinctive sign at first, but it’s the music that will guide you to the place that invented the slogan “Hog’s breath is better than no breath at all“.

Mallory Square and Surroundings

Main attractions:

• Mallory Square Sunset Celebration
• Mel Fisher Maritime Museum or Shipwreck Museum

The next area of Old Town that awaits us is the one that is concentrated around the famous Mallory Square. What makes this square famous is the so-called Sunset Celebration, the ceremony with which it greets the sunset every evening.  A number of attractions are concentrated in the area, some of a more commercial character, others of a remarkable historical and cultural nature.

Dedicating some time to this area allows you to get to know the history of Key West, which owes much to the activity of the so-called wreckers, the retrievers of objects from wrecks at sea, which were resold at the Mallory Square auction house. The Historic Memorial Sculpture Garden (a short distance from the Hog’s Breath) is dedicated to them, an open-air memorial where busts of the most eminent figures in Key West’s history, from President Truman to Hemingway, are also on display.

If you want to learn more about the wreck salvage business and the sinking of galleons on the shores of Key West you can visit 2 museums dedicated to the subject:

• the Shipwreck Museum displays relics salvaged from the Isaac Allerton, which sank in 1856, though it’s designed more as a sort of entertainment show than a museum. One of the arrows to its bow is the observation tower, which offers one of the best views of Key West
• the Mel Fisher Maritime Museum exhibits relics recovered from 2 Spanish galleons sunk in 1622, as well as silver found in fleets sunk in the first half of the 1700s. Less focused on entertainment than the Shipwreck Museum, it can boast far more interesting historical value

Within a block or so you will find other museums, first of all the Key West Museum of Art and History, housed in the beautiful historic building of the Custom House, where, in addition to learning a lot about the history of the town, you can also delve into the Oversea Highway, to which an entire section is dedicated, and Audubon House & Tropical Gardens, what was the first Victorian-style house in Key West and where an important ornithologist lived to whom we owe important studies on the birds of the area. In addition to the tropical garden, you can also visit the 3 floors of the house, expertly restored and full of original furniture and objects.

Walking along David Wolkowsky Street, skirting the old building of the Coast Guard Headquarters (which now houses Clinton Square Market), you will find the Key West Aquarium, where you can get up close to rare species typical of the Keys, including nurse sharks, giant isopods, sea turtles and alligators. Assisted by the staff, you can also feed the animals and, if you’re up for it, pet the tail of a shark.

Historic Seaport: Key West’s historic seaport

Main attractions:

• Flagler Station Oversea Railway Historeum
• Half Shell Raw Bar

After admiring the sunset over Mallory Square, it’s time to move on to the Historic Seaport, the last remaining area of Old Town to visit, which you can access from Front Street. This is an old wharf on the sea with an innumerable series of boats, fishing boats and restaurants (most of them touristy) and, apart from the pleasant walk, it doesn’t have many attractions to offer.

However, this historic port also has its own stories to tell: here the business of sea turtles was once concentrated, from a delicious and particularly sought after the soup was made. The turtles were captured in the Caribbean and shipped to Key West on schooners and then deposited in harbor pens called “kraals”, where they waited until they were slaughtered.

Turtle Kraals, today a restaurant, was opened in 1895 just in function of this business, which was then stopped in 1971, when the risk of extinction of turtles led to the enactment of a special law for their protection. The Turtle Museum, committed to the defense and conservation of these animals, carries out its outreach activities just a few steps from what used to be the old turtle warehouse.

2 other items of interest that you will encounter during your walk along the marina are the Norberg Thompson Memorial, dedicated to an entrepreneur and mayor whose activities contributed greatly to the growth of the port district, and the Flagler Station Oversea Railway Historeum, the end point of the Oversea Railway, the rail line that connected Key West to the mainland.

Passing through the area for dinner requires a minimum of selection so as not to end up in one of the crowded tourist restaurants in the harbor. My advice is to skip the first ones you come across and stop at the Half Shell Raw Bar, a very characteristic place with plates from all the states hanging on the wall, where you can eat well and not find the usual crowd.

If, on the other hand, crowded places are not a problem for you, then the best alternative is the Schooner Wharf Bar, although you will probably have to wait a bit to eat. For another interesting and especially reasonably priced option, if you don’t want too formal, head inland a bit and go to the picturesque B.O.’s Fish Wagon.

Attractions in other neighborhoods

Truman Annex: between Little White House and Fort Zachary

The Truman Annex area, which once coincided with the U.S. Navy’s military installation, is located west of Old Town and can also be reached on foot. There are essentially 2 ways to get there:

1. If you are on Duval or Whitehead Street, turn towards the sea at Southard Street to cross the Truman Annex Condominiums complex, and arrive at the Truman Waterfront Park traffic circle. Here you can decide whether to continue straight ahead (through the small Splash Pad water park) to get to the US Coast Guard Cutter Ingham Maritime Museum or turn left to get to the Fort Zachary area and the Florida Keys Eco-Discovery Center.
2. To reach the residential area of Truman Annex, which is located further north, you can also go back and turn left onto Emma Street, but the most convenient and “strategic” way is probably to return to the area after walking another stretch of Duval Street, again turning seawards at Caroline Street. In this way, after one block from the first seat of the historic Pan Am company, you will find yourself in front of the other important attraction of the area: the Truman Little White House.

Here’s what you can expect:

US Coast Guard Cutter Ingham Maritime Museum

This is an authentic museum ship with an important history, earning her one of the highest military honors bestowed on U.S. armed forces distinguished for acts of extraordinary heroism. When you visit this fascinating historic landmark, you can explore the bridge, combat information center, captain’s cabin, mess hall, engine room, store room, ammunition room and other rooms where you can get a detailed idea of what life must have been like on a military ship that fought in all the last major wars, including World War II and Vietnam.

Fort Zachary Taylor Historic State Park

In the nineteenth century, a plan to fortify the southeastern coast of the States was initiated, leading to the construction of Fort Zachary (completed in 1866) and Fort Jefferson (at Dry Tortugas). The Key West fort, named after President Zachary Taylor, was active until 1947 and is now an open-air museum where you can climb the walls and observe Civil War weaponry. The site is not just interesting for history buffs but also for those looking for a little sun and relaxation, as Fort Zachary Beach is located just 2 steps away from the old fort. We have already told you about it in our guide on the best beaches in Key West. There is an entrance fee to the fort and the beach.

Florida Keys Eco-Discovery Center

This center is an interesting opportunity to learn more about the flora and fauna of the Keys, especially since admission is free. One of the most interesting elements you’ll find inside is the reconstruction of the Key Largo Ocean Laboratory, the only underwater laboratory in the world. In addition to the Keys’ coral reefs, other habitats in the state, such as hammocks, pine forests, and beaches, are also explored.

Truman Little White House

Speaking of the 33rd U.S. President Harry Truman, who is part of the list of famous people on the island, here is his winter home called The Little White House (111 Front St.) where he and his family stayed from 1946 to 1952. Later, other presidents (Dwight Eisenhower, John Kennedy, Jimmy Carter and Bill Clinton) also continued to use it for official meetings and rest periods in the same way that other presidents stayed and sealed deals at the presidential residence at Camp David in Maryland. The house still has occasional government functions.

The cemetery area and Meadows

Towards the interior, there is an area of Old Town a little less trodden by tourism and pushing further east, the residential neighborhood of Meadows. The cemetery is definitely the main reason to come here but, since you’re in the area, it’s worth stopping by an interesting basilica and a beautiful memorial.

Key West Cemetery

Key West Cemetery sits at the foot of Solares Hill, the highest point on the island, and it is estimated that over 100,000 people are buried there. It was built in 1847 after a disastrous hurricane that swept away the previous cemetery, scattering the bodies of the people who were buried there, and is an expression of the so-called Rural Cemetery Movement, which promoted not only the relocation of cemeteries in outlying areas (at the time the dead were buried in the gardens attached to churches) but also their development according to aesthetic canons similar to city parks, in order to allow visitors to appreciate works of art and the beautiful surrounding landscape.

Besides cultural and aesthetic reasons, Key West Cemetery is also visited for the curious inscriptions found on some gravestones: for example those of B.P. Roberts, “I told you I was sick“, of Alan Dale Willcox, “If you’re reading this gravestone you desperately need a hobby“, and of Gloria Russell, “I’m just resting my eyes“.

The cemetery has several sections, some referencing important historical events (there are areas where Cuban independence fighters are buried, the crew of the ship USS Maine sunk in the Havana Proto in 1898, and sailors from the Confederate States) others are by ethnicity or religious affiliation. The best way to find your way around is to use the map you’ll be given at the entrance or to queue up for one of the guided tours available.

Basilica of Saint Mary Star of the Sea

With its Victorian and Renaissance Revival elements, the Basilica of Saint Mary Star of the Sea (1010 Windsor Ln.) is one of the most interesting churches in Key West and one of the oldest Catholic dioceses in Florida. One of the main reasons to visit is in the backyard, where a rosary-shaped path leads you to the natural rock grotto erected for Our Lady of Lourdes and Bernadette (Our Lady of Lourdes Grotto). The grotto was conceived in 1922 by Sister Louis Gabriel, who asked Our Lady to protect Key West from future hurricanes.

Bayview Park

A pleasant green area not far from the city cemetery with baseball, tennis, and basketball courts. From a tourist point of view, the main attraction of this park is the Key West Veterans Memorial Garden, dedicated to all those who have served (or are still engaged) in the American wars. In this beautiful memorial, each statue or sculpture represents a specific war, and the Vietnam monumental block is in my opinion one of the most successful.

Other attractions

Outside of Downtown, there are a few attractions that you could include in your Key West itinerary if you decide to stay 2 or 3 days (they are actually a bit off-center to easily fit into a short stay). Here are 2 to consider:

West Martello Tower and Garden Club

Garden Club (1100 Atlantic Blvd.) is a lovely tropical garden where you can walk along brick walkways (these are the remains of the West Martello Tower fort) among trees, plants, flowers, ponds and even gazebos that complete the pleasant setting. A small donation is requested for admission. The park is located in Higgs Beach, so it can easily be combined with a few hours of relaxation on the beach. Although it is not centrally located, it can still be walked to in about 15 minutes from Southernmost Point, however, if you are driving, you can take advantage of the ample parking nearby.

Key West Tropical Forest & Botanical Garden

The Tropical Forest & Botanical Garden (5210 College Rd.) is a great place to discover the endangered and threatened flora of the Caribbean and Keys. Inside, along convenient trails, you’ll find placid ponds and waterfalls as well as a remarkable variety of plants. It is located on Stock Island, the island east of Key West and is easily accessible by car from Old Town (just over 10 minutes).

The beaches of Key West

Key West may not boast the best beaches in Florida, but there is no shortage of opportunities for swimming: at the south end of Duval Street, in the Southernmost Point area, I have already mentioned South Beach, a small, very popular beach where you can relax on the sandy shore and swim in the shallow waters. Then, for a bit of romance, you can wait for the striking sunset on the pier.

Close to the already mentioned Higgs Beach, there is White Street Pier also called Edward B. Knight Pier. On this pier, with street lamps and benches, you can fish, watch the ocean, watch birds and admire sunrises and sunsets. At the end of the pier is a huge compass painted on the boardwalk. Looking for a special effect? In the evening when the wind blows, it’s striking to watch the waves crash against the fence; this is the time to take beautiful photos.

Not far from here, at 100 Atlantic Boulevard, Higgs Beach is a fairly large beach with tropical vegetation, picnic areas and a play area for the little ones. Nearby is Higgs Dog Beach (1500 Vernon Ave.), a small, rocky beach accessible to dogs.

One of the most popular among locals is Fort Zachary Beach and other possible shorelines are Smathers Beach and Rest Beach. For an in-depth overview I suggest you read our article entirely dedicated to Key West beaches.

Tours and tourist passes

Key West tours

Key West has remarkable tourist offers and there is no lack of activities to choose from. Here are the most interesting ones:

Cruises, snorkeling and dolphin watching in Key West

Key West can also be appreciated from the sea and, for a beautiful experience, you can consider one of the many cruises available. The choice ranges from sunset to the full moon, from private celebrations to special events without forgetting those organized on holidays.

• Dolphin Watching Cruise: If you love close encounters with marine life, this cruise will bring you into close contact with the dolphins that inhabit the Keys’ coastline.
• Dolphin Watching and Snorkeling Cruise: like the previous one, but with the possibility of snorkeling and admire the beautiful backdrops of this part of Florida.

If, on the other hand, you prefer something more classic, framed by the unforgettable atmosphere of the sunset while perhaps sipping a glass of sparkling wine, you can refer to the cruises that make the “sunset celebration” their strong point.

• Sunset Cruise: a two-hour cruise with a small buffet and drinks to enjoy on board while watching the sun fade on the horizon.
• Cruise on a transparent bottom boat: the particularity of this cruise is that it is done on a boat with a transparent glass bottom so that you can observe the seabed of the Keys. If you choose the “sunset” option among the various departure times, the price of the cruise will include a toast with a glass of Champagne.

If you are more of a sporty type, there is also the possibility of snorkeling and a kayak tour along the magnificent seabed of the Keys.

Helicopter tour over Key West

Helicopter tours are becoming more and more popular in the United States, because they combine a relatively low price with the possibility of seeing the beauty of the country from an unusual and panoramic point of view.

Even Key West has not escaped this trend, and you’ll have the possibility to choose from various tours, each of which is aimed at a specific category of tourists. Here are the main options you’ll have at your disposal.

• Key West Discovery Flight: the “basic” tour: we can define it as the “basic” tour because with a duration of only 5 minutes it will still allow you (at a reasonable price) to have an overall view of the Key West coastline. If you want you can choose a similar version of this tour but at a slightly higher price for a 10-minute duration. Recommended for those who want to enjoy a longer flight without spending too much.
• Key West Ultimate Island Experience: this tour allows us to have a much more complete experience than the previous one since we will spend about 30 minutes flying over the beauty of this part of Florida. There are several options to choose from during the day and you can adapt it to your itinerary.
• Key West Sunset Celebration: do you want to combine the charm of seeing the Key West coastline from above with the beauty of the sunset? By choosing this activity you can do so. Particularly recommended for those with a romantic side, the entire tour will last about 30 minutes and, as you might guess, only leaves once a day.

Excursion to Dry Tortugas National Park

A day trip that can only be done by boat (Yankee Freedom Ferry-100 Grinnell St.) and seaplane (Key West Seaplane Adventures-Key West Airport) is to the Dry Tortugas National Park, 68 miles west of Key West. It’s a classic destination, not to be missed by those with a little extra time on their hands.

The national park authority preserves the island of Garden Key, occupied almost entirely by Fort Jefferson, and seven other small islands, the most isolated of the Florida Keys, and consequently those with the seabed that has been least affected by man.

The evocative blue waters, the coral reef, the marine life and the conspicuous presence of birds make you fall in love with this oasis of peace that is a UNESCO World Heritage Site. Here you can practice snorkeling, kayaking and scuba diving, you can camp on Garden Key and enjoy pleasant picnics. The park can be visited with guided tours or on your own.

Miami and Key West Explorer Pass

 

If you want to save money without sacrificing the wonders of Key West, you can consider buying this pass which, including the Miami area, gives you a choice of 3, 4 or 5 attractions at your leisure, including a glass-bottom boat cruise and snorkeling, a bike rental and a Key West train tour. Find a list of activities to choose from at the link below.

More info on the Miami and Key West Explorer Pass

If you are also particularly interested in the possibility of including as many attractions as possible in your vacation, not only in Key West but also in the Miami and Fort Lauderdale area, you can read our article dedicated to Miami Passes.

Key West Events

 

Key West is a lively and active city where residents love to have fun at village festivals. If you have the chance, it can be worth visiting Key West to coincide with an event. Here are a few examples: if you love good food in January there is the Key West Food & Wine Festival with food demonstrations, food tours and food and wine tasting. Events are ticketed and held at a variety of locations.

In July there is The Key Lime Festival with food and drinks containing lime, such as the famous Key Lime Pie, Key Lime Cocktail and Key Lime Rum. You can also participate in the best pie eating contest!

The merriment explodes in October at the free event called Annual Goombay Feast in the Bahama Village neighborhood, when people dance in the streets, parade in costume, visit arts and crafts stalls, and there is live entertainment with gospel and reggae music.

In Key West, as in the rest of the States, the celebration of Halloween is very popular; here it is celebrated with the event called Fantasy Feast in downtown and in the Historic Seaport and on this occasion extravagance pervades the area starting from the costumes that parade the streets, where we also find the inevitable food and craft stalls.

Where to eat in Key West

In the city there is a big choice of restaurants; moreover we are in a place by the sea and the fish that are most popular are snapper, grouper and mahi mahi. A typical dish is conch fritter but it is a real crime to visit Key West without eating Key Lime Pie. The one at Blue Heaven (729 Thomas St.) is amazing, or alternatively try the one at Kermit’s Key West Key Lime Shoppe (200 Elizabeth St.).

As for the places to try, I have already mentioned several along the itinerary, although not all of them are worth a stop. The ones I recommend you consider for dining are:

• Blue Heaven (729 Thomas St.) in Bahama Village
• Half Shell Raw Bar (231 Margaret St.) and B.O.’s Fish Wagon (801 Caroline St.) in Old Historic Seaport
• Hog’s Breath Saloon (400 Front St.) near Mallory Square
• Café Marquesa (600 Fleming St.) if you’re looking for a fine dining restaurant not far from St. Paul’s Episcopal Church

To have a simple drink instead opt for:

• Capt. Tony’s Saloon (428 Greene St.), in the Old Town area, 2 blocks from Mallory Square
• The Rhum Bar (1115 Duval St.) not far from the Southernmost point
• Green Parrot Bar (601 Whitehead St.), not far from Bahama Village
• Hog’s Breath Saloon (400 Front St.) near Mallory Square

If you want to save money, you can fall back on the many Cuban sandwich shops, which in the context of Key West’s expensive restaurants can be good allies. I stopped at Frita’s Cuban Burgers (425 Southard St.), a pleasant place for its atmosphere and the owner’s friendly nature and my sandwich was not bad. There is also a lot of choice for ethnic cuisine: at Amigo Tortilla Bar (425 Greene St.) the cuisine is Mexican and the atmosphere is fun and friendly, while at El Meson de Pepe (410 Wall St.) the cuisine is Cuban, as is the live music.

Where to sleep in Key West

There are several options for overnight stays in the city especially for those who like cozy B&Bs. The area to look for is Old Town, which is very convenient for getting around all the city’s attractions on foot but not very cheap especially during the high season. We have selected a number of recommended facilities, which you can read about in our guide dedicated to this topic by clicking on the link below:

Where to stay in Key West

Key West Video

Thanks to this video you can admire the beautiful stretch of road of the Overseas Highway and the main things to see in Key West.

Key West weather: when to visit

Key West boasts a tropical climate: a dry season with pleasant temperatures alternating with a warmer and more humid one. Unfortunately, sometimes nature damages this paradise, as in the case of Hurricane Wilma in October 2005 and recently Irma in September 2017; dramatic events that each time have brought out the tenacity of the population, which in these circumstances has proved ready to roll up its sleeves to return Key West to its usual splendor.

For more details on the best time to go to Key West and the surrounding areas, please read our article entirely dedicated to Florida’s particular climate.