Key West is an island city that is part of the Florida Keys and is the southernmost piece
of land in the continental United States.
The island is located about 160 miles southwest of Miami and 90 miles north of Cuba and is
bordered by both the Atlantic Ocean and the Gulf of Mexico.
In this video, we’ll provide an overview of our December 2019 visit to Key West, when
our ship -- the Disney Magic -- docked at Pier B on the west side of the city.
Please note there are three cruise docks in Key West.
Ships that dock at Mallory Square and Pier B are located just steps away from many popular
attractions.
However, passengers on ships that dock at the Navy’s Outer Mole Pier are required
to take a complimentary shuttle through the naval base to explore Key West on foot.
We checked Key West’s website prior to our visit to determine where our ship was scheduled
to dock and we’ve linked to the website in the description below.
During our visit, we explored Key West on foot and by riding the city’s free Duval
Loop bus service.
The hop-on / hop-off service makes 18 stops in the tourist area of Key West and the city’s
website includes a map of the route and a link to real-time tracking of the bus.
We’ve linked to the website -- and a map of the places we visited -- in the description below.
After disembarking from the ship, we walked from Pier B toward Mallory Square.
Along the way, we passed the Key West Art and Historical Society building, where our
Jellybean enjoyed taking photos with artwork located outside.
There were a number of shops and markets in and around Mallory Square, including The Key
West Sponge Market.
The market’s sponge man is a popular photo op and restrooms were located nearby.
The Key West Historic Memorial Sculpture Garden was also located in the area and featured
busts of people who have had a significant impact on the city.
And the nearby cultural center featured a restaurant, gift shop, and museum that offer
a glimpse into the island’s Cuban heritage.
Restrooms were available inside.
From Mallory Square, we crossed Wall Street to the lime-colored Kermit’s Key West Key
Lime Shoppe, which offered free samples of their many Key lime-flavored products.
We exited Kermit’s on the Front Street side and continued north to the Duval Street intersection,
which had a CVS on the corner.
We followed a sign at the intersection that pointed the way to Simonton Beach and continued
along Front Street until we reached Simonton Street, where we turned left to stop by one
of the two beaches we visited while in port.
Simonton Beach is a small beach located about a 5 to 10-minute walk from the Mallory Square
and Pier B docks.
Key West is not known as a beach destination because the third largest coral barrier reef
system in the world protects it from large waves and most of the beaches in the Florida
Keys are man-made.
After visiting the beach, we headed back inland -- toward Front Street -- and continued along
Simonton Street to Key West First Legal Rum Distillery, which was appropriately named
since it claimed to be the first legal rum distillery in Key West.
During our visit, guests were offered a free tour of the distillery and one free sample
of rum and you could sample all of the rums if you purchased one of the distillery’s
shot glasses.
As we continued further inland along Simonton Street, we stopped at the Hemingway Rum Company’s
Papa’s Pilar Rum Distillery at the intersection of Greene Street.
Samples of the rum were available for free, but a fee was charged for the hourly distillery tour.
From the distillery, we followed Greene Street northeast to another Kermit’s Key West Key
Lime Shoppe, which was full of the same products as the other shop, but was significantly less busy.
Daddybean took the opportunity to enjoy one of his favorite desserts: a delicious slice
of Key Lime Pie.
We continued to walk northeast along the water to the Cuban Coffee Queen, where I ordered
a cafe con leche.
The side of the building featured a large painted mural of a vintage Key West postcard,
which was a nice photo op.
A large wooden directional distance sign that is commonly used to depict Key West was also
located nearby and made for another fun photo op.
With our sightseeing on the northwestern side of the city complete, we took the Duval Loop
bus to South Beach.
The real-time tracking of the bus made it easy to finish up our Key lime pie and coffee
just in time to hop on board.
South Beach is a public beach with a small pier that is located on the southwest side
of the island at the end of Duval Street.
Leaving the beach, we walked southwest along South Street to the historic Southernmost
House, which was built in the late 1800s and was the southernmost private residence in
the United States and is now an adults-only hotel.
We continued walking to the intersection of Whitehead Street, where a long line of tourists
were waiting to take their photo with the large iconic “Southernmost Point of the
Continental USA” concrete buoy.
Because of the long line -- and the fact that the landmark is not technically the southernmost
point in Key West -- we decided to not stand in line and simply stood to the side and took
our selfie while those in line switched out for photos.
We did take a moment to read the historical marker on the nearby, unassuming concrete building.
According to the marker, the building was put in place over 100 years ago to protect
the connection between the land line and underwater telegraph line that linked Key West and Havana, Cuba.
Since we were only about a mile from our cruise ship, we decided to continue walking along
Whitehead Street and reached the Key West Lighthouse & Keeper’s Quarters Museum about
5 minutes down the road.
The lighthouse was built in 1848 and visitors can walk the 88 steps to the top -- for a
fee -- to experience the highest viewpoint on Key West.
Just across the street from the lighthouse is the Ernest Hemingway Home and Museum, which
offers tours of the author’s estate and gardens for a fee.
Continuing along Whitehead Street, we came to the very popular Mile Marker Zero photo
op that marks the beginning -- and end -- of US Highway 1, which stretches from Key West
to the Canadian border in Maine.
During our visit, there were a few groups waiting to take a photo with the US 1 “Begin”
sign, so we crossed the street and took our photo with the US 1 “End” sign, which
seemed to have gone unnoticed by other tourists.
Further along Whitehead Street, we came to the birthplace of Pan American World Airways.
The historic building was home to a brewery and restaurant during our visit.
On the opposite side of Whitehead Street were Key West’s historic Presidential gates,
which have welcomed US Presidents and other dignitaries since 1906.
We took a bit of a detour through the gates -- along Caroline Street -- to the Truman
Little White House, which was the winter White House for President Harry S. Truman.
Tours of Florida’s only presidential museum are available for a fee.
Backtracking to the gates, we continued walking along Caroline Street.
We passed the Captain George Carey House -- which reportedly sits on the site where pirates
discovered fresh water in the 1700s -- and then we came to The Bull & Whistle Bar and
the Garden of Eden clothing-optional bar at the intersection of Duval Street.
We didn’t visit the bars, but we turned left on Duval Street -- toward our ship -- and
eventually came to Sloppy Joe’s Bar, which has been at the corner of Duval Street and
Greene Street since 1937.
Around the corner -- on Greene Street -- is Captain Tony’s Saloon, which was immortalized
by Jimmy Buffet’s song “Last Mango in Paris” and features numerous license plates,
bras, and dollar bills attached to the ceiling.
The saloon was the original location of Sloppy Joe’s Bar and was frequented by Ernest Hemingway
at that time.
A large, preserved fish sits atop the saloon's sign outside and it’s said that throwing
a quarter -- backwards -- into the mouth of the fish will give you good luck until you
leave the island.
As we headed back to the ship to leave the island, we realized that perhaps the lucky
fish should have been the first stop on our Key West adventure.