Florida Keys Tours
Whether you’re hoping to learn the history or see the sights, there are
many tours you can follow to see more deeply into the little island. Decide
what you want to see—and how, since you can walk, ride, or boat—and
grab your camera.
Walking Tours
Trails of Margaritaville – Get off your perch and get some sun while
you learn the stories and see the landmarks left by one of Key West’s
most famous residents, Jimmy Buffet. Don the shark-fin hat you’re presented
with and follow your Hawaiian-bedecked guide as he passes Buffet’s old
homes and haunts, and his current recording studio. Tours begin at 4 p.m. at
Captain Tony’s Saloon, 428 Greene Street (right off Duval) where Buffet
used to play, and end 90 minutes later at the Margaritaville Café so
you can enjoy some liquid refreshment without delay. Reservations are required;
please call 305-292-2040.
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Tour the Backcountry of the Florida Keys |
Ghost Tours of Key West – For those who prefer the cool evening air,
this wildly popular tour takes visitors on an hour-and-a-half stroll through
historic Old Town while your lantern-lit guide recounts tales of ghosts, graves,
and horror. Featured in programs aired on the Discovery, History, Travel, and
Learning Channels, Ghost Tours of Key West is the busiest on the island. The
tour is wheelchair-friendly and covers one half mile of ground. Reservations
are usually required; call 305-294-walk to reserve space. Rain or clear, tours
depart at 8 and 9 p.m. from the Crowne Plaza la Concha Hotel at 430 Duval Street.
ExentriTours – Another offbeat tour focuses on the “strange and
scandalous” aspects of Key West history, such as the pirate operations
and drunken government officials. This hour-long tour covers about a mile of
land and allows tourists an inside look into Key West’s strange but true,
and sometimes illicit, story. Tours depart at 4 p.m. daily from the Sippin’
Coffee House at 424 Eaton Street. Reservations are required; please call 305-292-1918.
Key West Literary Seminar Writers’ Walk – Operational between December
and April, this twice-weekly walk takes literature lovers on an outdoor tour
of the island’s famous writers: Ernest Hemingway, Tennessee Williams,
Shel Silverstein, and others. The tour covers one mile and lasts one hour, and
departs at different times, from different places, on different days. For a
less confusing schedule and to make reservations, call 888-293-9291.
Self-Guided Walking Tours
Pelican Path – This map and accompanying historical briefs educate visitors
as they stroll past landmarks and historic homes. Published by the Old Island
Restoration Foundation, the guide is available at the Chamber of Commerce in
Mallory Square.
Sharon Wells’ Walking & Biking Guide – This FREE information-packed
64-page guide includes 10 self-guided tours that enlighten readers, as well
as several shorter “mini-tours” on Key West’s literary history
and its gay & lesbian community. Also included is a suggested list of nature
trips around the Keys. Maps and highlights are neatly organized and thoroughly
informative. You can find free copies of the guide all across the island at
more than 200 retail locations, and at the chambers of commerce offices at most
of the larger upper keys.
Trolley Tours
Conch Tour Train – Relax in the shade as your guide drives you all over
the island, spouting bits of history, folklore, and stories of Key West. One
of the best things about this tour is the fact that it’s a continuous
90-minute loop around the island, and a ticket is actually a day pass. So between
learning the lore, you can debark to shop, dine, or stroll—and then get
back on another train and finish your education. Tours depart from Mallory Square
between 9 a.m. and 4:30 p.m., and visitors from the northern end of the island
can park for free at the Key West Welcome Center and take a shuttle to the square.
Old Town Trolley Tours – This trolley tour is much like the Conch Tour,
in that you can get off and back on at any stop you like, though this circuit
also stops at many of the island’s major hotels. It leaves from the Key
West Welcome Center between 9 a.m. and 4:30 p.m. daily.
Tour by Sea
Key West Historic Harbor Tour – Seafarers might prefer this harbor cruise
aboard a 49-passenger power catamaran, which takes them from the Ocean Key Resort
Marina into the beautiful waters surrounding the island. The narrated cruise
covers Civil War stories, tales of wreckers and shrimp boats, and the sinking
of the US battleship Maine. See the Key West Historic Seaport, Fort Zachary
Taylor State Park, Wisteria Key, the Hilton Resort & Marina, Sunset Key,
and old Overseas Railways docks. The 90-minute cruise departs at 4:30 p.m. and
returns by way of the Key West Aquarium and Mallory Square, just in time for
passengers to enjoy the sunset. The tour is run by the Subtropic Dive Center,
and reservations can be made by calling them at 305-296-9914.
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