Key West, originally Cayo Huesto or the Isle of Bone, is the southernmost point of Florida. Once a burial ground, the island has faced both tremendous wealth due to the scavenging of nearby shipwrecks, and near poverty due to limitations on travel to the city.
In 1982, when the U.S. government installed a checkpoint on the one road from the island to the mainland in an attempt to prevent illegal immigrants from reaching the mainland, transportation to the island halted threatening businesses. Key West therefore seceded from the U.S., declared war, then surrendered and asked for foreign aid, all in an attempt to draw attention to the island's plight. The restrictions were lifted, and Key West once again became a popular tourist spot.
Even now there are only three ways to get to Key West: drive down Route 1, fly into Key West Airport, or charter a boat. The cheapest means is to drive, but you do not have to drive the two hours from the mainland to Key West yourself; there are several bus companies which will take you down and back again. It is important to understand that there is only a single road from mainland Florida to Key West, which is a two-lane road of bridges between islands. In some areas the road goes down to one-lane, so if there is an accident or traffic becomes backed up you may be stuck for hours. However, the cost of driving is much less than a plane making it the most frequent mode of transportation. While some cruises can take you from the mainland to Key West, these are mostly day trips, rather than a means of transportation.
But Key West is worth the day of travel to reach; the island houses the former home of Ernest Hemingway where he lived in the 1930s (now a museum), Truman's Little White House (also now a museum), and the Southernmost Point where you will find yourself closer to Cuba (90 miles) than the nearest Wal-Mart (158 miles). The island has beautiful beaches, warm oceans, excellent bars, scuba diving, snorkeling, fishing, guided jet ski tours, and open ocean glass-bottom boat kayaking.
If you're only spending four days in fun and fabulous Key West, here are the things you absolutely have to do:
1) Spend a Day the Hemingway Way
Clearly Unique Charters Glass Bottom Kayak & Snorkel-Tour (231 Margaret St, 305-747-8651)
9 a.m. to 5 p.m. daily
$89
If there's one thing Hemingway loved it was a good adventure. So start your day off with a glass bottom kayak tour. A boat brings you out to the shallows, then a guide leads your group over the shallow waters of the reefs -- in your very own glass-bottom kayak. After an hour or so you can hitch your kayak up to the boat and snorkel with the sting rays, nurse sharks, octopi, and tropical fish until the time is up. There are two 3-hour trips daily; one leaves at 10 a.m., the other at 3 p.m. Call or visit to make a reservation.
Have Lunch at Captain Tony's (428 Greene St, 305-294-1838)
10 a.m. to 2 a.m. daily
The site of the "original" Sloppy Joe's, where Hemingway used to spend his evenings before the rent was increased and Sloppy Joe's Bar moved down the street.
Hang Out at the Ernest Hemingway Home & Museum (907 Whitehead Street, 305-294-1136)
9 a.m. to 5 p.m. daily
$13 adults
Ernest Hemingway lived at his home in Key West from 1931 to 1939 with his second wife Pauline, and sons Gregory and Patrick, as well as several six-toed cats. Descendants of these cats still have run of the grounds where tourists come to see Hemingway’s writing room and famous salt water pool.
Guided tours start with some history of the house, which was built in 1851 by Asa Tift, and has one of the only dry cellars on the island, due to the location of the house being the second highest point in Key West (16’ above sea level). The tour then proceeds clockwise through the first floor then the second floor where family photos, mementoes from Hemingway’s time in the wars, and Hemingway’s art collections are kept before heading outside.
Visitors cannot enter Hemingway’s writing studio on the second floor of the guest house, but they may view the room where he wrote To Have or Have Not through the doorway. Below the studio are public bathrooms and the gift shop overlooking the first pool in Key West. The gardens include a cat cemetery and a urinal from the original Sloppy Joe’s which Hemingway brought home and turned into a fountain. According to tour guides, Hemingway took the urinal when Sloppy Joe’s was moving to Duval Street because he said he had used it so much that he already owned it.
The tour guides tell various detailed anecdotes about the furniture, the changes made over the years to the house, and Hemingway’s life in Key West. Be sure to look for a small abstract statue of a cat in Hemingway’s bedroom; it is a copy of the original statue by Pablo Picasso given to Hemingway by the artist. The original was stolen in 2000 by a visitor to the museum.
Have Dinner at Sloppy Joe's (201 Duval Street, 305-294-5717)
9 a.m. to 4 a.m. (Opens noon Sundays)
21+ after 9:30 p.m.
Key West has many excellent restaurants and bars, but the place that everyone wants to go to is Sloppy Joe's. Opened the day prohibition was repealed in 1933, Sloppy Joe's now features a live band daily on a raised stage, making the acts easy to see from most places in the bar. In addition to the main bar, there are two smaller bars in the establishment, as well as a beer room. But most importantly, it is the bar Ernest Hemingway frequented during his years living in Key West. (However, when Ernest Hemingway first visited the establishment it was down the street at the current location of Captain Tony's.) Décor therefore includes photos of Ernest Hemingway, and one wall features the photos of the winners of the annual Papa Look Alike contest which has been held in July around Hemingway’s birthday for 33 years.
While you're here, try a Sloppy Joe ($9.75). The sandwich is large and delicious, and a staple at this establishment. Also try the conch fritters ($9.25 for 6), which are a specialty in the Keys and a very tasty dish here.
For drinks, try the Papa Dobles ($8) a refreshing combination of rum, grapefruit juice, sweet and sour, club soda, and lime juice, which was purportedly one of Hemingway's favorites. The Sloppy Rita ($8.75) is Sloppy Joe’s twist on the margarita, and is another crowd favorite. The Koozie of mixed drinks are a little more expensive, but refills are cheaper than a second drink, and the Koozie is yours to keep.
2) Take a Day to Explore the Island
From the Southernmost Point back to Mallory Square
Southernmost Point Buoy (South St & Whitehead St)
All Hours
Free!
It is said that at this point you are closer to Cuba (90 miles) than to the nearest Walmart. Pretty soon they will probably have a Walmart in Cuba, so you should visit while this is still true! Go early in the morning to beat the crowds and get the best pictures.
Key West Butterfly & Nature Conservatory (1316 Duval St, 305-296-2988)
9 a.m. to 5 p.m.
$12
This conservatory houses 50 species of butterfly, 20 species of exotic birds, and thousands of plants all in one climate controlled glass habitat, which guests are invited to walk through. Inside the habitat are pathways and a gazebo, and the butterflies and birds fly freely. Be sure to watch where you step to avoid harming the animals; also, quiet guests may find themselves rewarded by being landed on by the butterflies.
Light House & Keepers Quarters (938 Whitehead St, 305-294-0012)
9:30 a.m. to 4:30 p.m.
$10 ($5 for students, $9 AAA)
Across the street fom the Hemingway House is the Key West Lighthouse, erected in 1848. The original lighthouse was destroyed in the hurricane of 1846, and its keeper, the widow Barbara Mabrity, stayed on as keeper when the new lighthouse was built at its current location further inland from the original and 14' above sea-level, making it a literal high-point on the island. So be sure to climb the lighthouse's 88 steps for a breathtaking view of Key West.
Little White House (111 Front St, 305-294-9911)
9 a.m. to 5 p.m.
$16.13 (reduced rate for online purchase)
Presidemt Truman chose to spend his presidential winters here -- a grand total of 175 days -- and it's easy to see why. Truman's Little White House is a unique building in this beautiful town. Originally built as the first officers quarters for the navy base, this house had a spectacular view of the ocean before other buildings were placed between it and the sea. The quarters were later converted to a house, and ever since it has had many VIP visitors, including President Taft, Thomas Edison, and President Kennedy.
The tour includes a short film, and a guided tour where visitors can see Truman's unique poker table which was designed to easily convert into a regular table due to his wife's disapproval of the game, the so-called "red phone," and Truman's desk complete with personal belongings.
Old Trolley Ghosts and Gravestones Tour (501 Front St -- i.e. Mallory Square, 305-294-4678)
Evenings
$33.60 (reduced rate for online purchase)
The hour-and-a-half guided tour shows visitors the more macabre side of the island. Included is the old civil war fort which houses the haunted doll known as Robert, and the site of Key West's haunted gallows.
3) Explore the Waters for a Day
Fort Zachary Taylor Beach (300 Truman Annex, 305-295-0037)
8 a.m. to Sundown daily
$2 per pedestrian/cyclist, $6 per car (up to 8 occupants)
Originally built to protect Key West, the fort is now part of a large national park. the beaches are beautiful, and snorkling among the rocks will allow you to see tropical fish. The on-the-beach Cayo Huesto Cafe offers light refreshments, including beer which you are asked to consume on their deck rather than on the sand.
HydroThunder Jet Ski Tour (Zero Duval St, 305-842-1880)
9 a.m. to 5 p.m.
$130
This 90 minute guided tour takes you around the island on jetskis, giving you a whole knew perspective of the island and surrounding waters. Tour leaves from the Hyatt Resort every two hours starting at 9 a.m. and covers 27 miles of coastline. Be sure to wear clothing that you don't mind getting wet, secure & comfortable shoes, and sunscreen.
Key West Aquarium (1 Whitehead St., 305-296-2051)
10 a.m. to 6 p.m.
$14 ($12 for students)
The Key West Aquarium might be small, but what it lacks in size it makes up for in heart. The 1930s aquarium includes an outdoor area where injured sea turtles can enjoy the ocean waters while being protected from predators and humans by a fence barrier. Off to the right is a tropical exhibit room with an extremely natural feel. The aquarium also has a "touch tank," where visitors can touch some of the animals, and guides show stingrays and nurse sharks to visitors.
4) Visit the Dry Tortugas
Fort Jefferson (Garden Key, 305-242-1100)
Sunrise to Sunset
$5 Entrance Fee
Construction of Fort Jefferson on Garden Key in the Dry Tortugas started in 1800s, and while the six sided building was never completed it has been used as a prison before becoming a historical site. It housed Dr. Samuel Mudd who had been arrested for assisting John Wilkes Booth after he assassinated President Lincoln.
Approximately 70 miles west of Key West, a visit to the Dry Tortugas will take an entire day. There are two options for reaching Fort Jefferson: you can take a day cruise or travel by sea plane. While the day cruise on the Yankee Freedom (800-624-0939) takes longer -- boarding in Key West is at 7 a.m. daily arriving at the Dry Tortugas at 10 a.m., with the return trip departing at 3 p.m. and arriving in Key West after 5 p.m. -- it is far less expensive ($165 for adults, $155 for students) and includes a continental breakfast on the boat and sandwich buffet lunch on the island. However, many people find that the long trip on the ocean causes motion sickness, making the trip unpleasant.
Key West Sea Plane Adventures (305-293-9300) costs $280 per adult and takes about 40 minutes each way. The half day excursion travels twice a day to and from Fort Jefferson, allowing visitors to spend more time on the island exploring and less time traveling. Taking the sea plane also gives visitors the opportunity to see wildlife in the ocean during the journey, including sea turtles and sharks, and several shipwrecks are also visible by plane. If you travel by sea plane, rental of a cooler, flippers, and a mask are included in the flight fee.
Once on the island, visitors can explore the historical fort, lounge on the beaches, and swim in the warm, clear waters around the fort. Wildlife visible while snorkeling around the fort includes exotic fish, nurse sharks, sea turtles, stingrays, and the occasional octopus. Pieces of wreckage, birds, and coral can also be seen while snorkeling.
The island has no running water, no restrooms, no restaurants, and no trash receptacles. It is important, therefore, to plan ahead. Visitors are encouraged to bring a cooler of food and drinks, and when the cruise ship is docked at the island its restrooms are open to the public. Camping is allowed, but campers need a permit ($3 per person) and are asked to remove all trash from the island when they leave. Grills and picnic tables are available for use on the island, but campers must bring their own self-starting charcoal; flammable liquids (e.g. lighter fluid) and bonfires are not permitted on the island. A small gift shop on the island sells souvenirs, snacks, and drinks, but only accepts cash.
Finally, if all that isn't enough for you and you're looking for a place to stop on your way down to Key West, and are a movie buff, be sure to stop in Key Largo to see the actual African Queen, the boat from the film of the same name.
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