Tours
Hoping to catch some local history while in the Florida Keys? Want to make sure you hit all the hot spots while you’re here? Want to learn about the lesser-known corners of Key West? Take a tour! These days there are so many tours and specialty tours to choose from it’s better to arm yourself with information about them before taking the plunge.
Whether you want to walk the local streets of Key West and explore hidden corners with a local resident, or ride a trolley train over the old Seven-Mile Bridge in Marathon, there are lots and lots of tours you can join to learn more, see more, and have more fun. Since there are more tourists, residents, and buildings per square feet in Key West than in the other Keys, there are more tours to pick from in that city.
As for trolley and train tours, well, they look more hokey and ridiculous than anything, but they are one of the best ways to get around Key West and see the highlights, for example, or to get out to Pidgeon Key in Marathon, to cite another example. They look silly, but they get the job done right, and hey, you’re on vacation anyway, right? Don’t worry, locals understand and the other tourists are in the same “boat”, so to speak!
Choose your Tours
Choose the perfect tour according to your interests and according to your sense of adventure and comfort levels. That means don’t go for a long walking tour of Key West in the full sun if you think you’re going to be deeply affected by the heat. It does get hot here, and the streets of Old Town get super hot when the sun beats down and the buildings block any cooling breezes that may relieve the other parts of town. Instead, opt for a trolley tour or the conch train tour. Don’t go for a full day offshore fishing trip in rough seas if you’re not sure whether you’re prone to sea-sickness. Book a half-day trip instead, or book a flats fishing trip, or a glass-bottom boat tour of the reef. There are so many different types of tours there’s no need to book something that isn’t exactly what you want for yoru Florida Keys vacation.
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.