Taking a tour allows you access to places and stories that many visitors to the Florida Keys don’t get to experience, such as the untouched backcountry and the six-toed cats that haunt the Hemingway House and pool. Enjoy the scenery as you listen to tales of wreckers, pirates, hurricanes, and the many colorful characters that have lived in Key West over the years. Keys natives and historians guide most tours, and they’ll take you around the islands on foot, in trolleys, in boats, and even by air.

Walking Tours

Ghost Tours of Key West

Learn about the island’s infamous ghosts and pirates during this evening stroll through the haunted alleys of historic Old Town. Your ghoulish guide will lead you through the graveyard as he lantern-lit guide relates ghastly tales that have (at the very least) a basis in Key West’s true history. You’ll walk about one half mile in an hour and a half, and it only adds to the atmosphere if it’s raining. Tours depart from the Crowne Plaza la Concha Hotel on Duval Street at 8 and 9 p.m. Reservations are strongly recommended, as the Ghost Tour is Key West’s most popular; call 305-294-walk.

Trails of Margaritaville

Despite the onus of having to wear a shark-fin hat, you’ll certainly enjoy hearing stories about Buffet’s early days on the island, before his name became synonymous with Key West. Your guide, clad in a loud Hawaiian shirt, will lead you from Captain Tony’s Saloon, one of Buffet’s original venues, past his favorite bars, his homes, and his studios. Tours meet at 4 p.m. at 428 Greene Street and end up an hour and a half later at the Margaritaville Café on Duval. It’s such an experience that reservations are required to ensure you don’t miss out.

Key West Literary Seminar Writers’ Walk

Learn some literature lore as you stroll through Old Town Key West. Your guide will recount facts and legends about Key West’s many famous writers, not the least of whom was the illustrious Ernest Hemingway. Others include poet Shel Silverstein, playwright Tennessee Williams, and Dennis Lehane, author of Mystic River. The one-hour Writers’ Walk runs twice weekly from December to April, but you’ll have to call for specifics as the tour keeps no set schedule or point of departure.

Self-Guided Walking Tours

Sharon Wells’ Walking & Biking Guide

This 64-page guide maps ten self-guided tours and several shorter walks that cover the gay & lesbian and literary aspects of Key West. Nature enthusiasts will appreciate the inclusion of nature trail trips chosen to display the extraordinary beauty of the Florida Keys. The guide is free at locations throughout Key West and at the chambers of commerce offices of the northern keys.

Pelican Path

Published by the Old Island Restoration Foundation, the Pelican Path map corresponds to markers set up at historic points throughout the Old Town section on Key West. Available at the Chamber of Commerce in Mallory Square.

Crane Point Hammock Marathon

Wind along the two and a half miles of this self-guided eco-tour, stopping at the Museum of Natural History, the Marathon Wild Bird Center, and the pirate-themed Children’s Museum. Also on the 64-acre site is the Adderly Home, made of a shell concrete in the 1890s. The Nature Center houses reptiles, and the hardwood hammocks along Florida Bay are a favorite spot of wading and raptor birds. Call to arrange a trolley tour; no reservations required for hikers. Located at MM 50.5Bayside.

Bike Tours

Lloyd's Key West Nature Bike Tour

Bike through the lesser-travelled streets of Key West to beaches and beds of tropical foliage. Lloyd lets you taste real Key Limes and other indigenous fruits, and inhale the perfumes of frangipani, gardenia, and jasmine blossoms. The bike tour won’t require you to be in top condition—the trail is even and the pace leisurely. Tours depart from the Moped Hospital (601 Truman Avenue) at various times, which you’ll need to call for though reservations aren’t necessary. The tour costs $15 plus $3 for a bike.

Trolley Tours

Old Town Trolley Tours

This is a great two-in-one bargain a narrated tour and an economical way to get around Key West all day. Plus, you’ll feel like a true tourist as you sit in the open-air streetcar-style trolleys: shaded, comfortable, and regaled with stories of pirates, Indians, battles, and wreckers. Your ticket buys you unrestricted access to a full day of riding and listening. The trolley takes 90 minutes to complete a loop around the island, and one should reach each of the nine boarding stops every 30 minutes. You can get on and off as many times as you like. Tours depart from Mallory Square between 9:30 a.m. and 4:30 p.m., 365 days a year. Park at Mallory Square or the Hilton garage.

Conch Tour Train

The famous Conch Train sightseeing tour concentrates its attention on the historic Old Town area of Key West. The little train winds its passenger cars down Duval Street, past the Hemingway House, and stops at the Historic Seaport and Mallory Square and the Historic Seaport. Tours depart from Mallory Square between 9 a.m. and 4:30 p.m., every half-hour. Park at Mallory Square or the Hilton garage.

The Bone Island Shuttle

Though this isn’t technically a tour since it isn’t narrated, it’s got two other advantages: it’s dirt cheap ($8 per all-day pass), and it’s air-conditioned. You’ll pass many of Key West’s historic spots while encased in the luxury of cool air, and if you bring along one of the self-guided walking tour maps you can learn quite a bit by yourself. The shuttle operates from 9 a.m. 10 p.m. daily and runs two routes: one clockwise, one counterclockwise around Key West.

Tour by Sea

Key West Historic Harbor Tour

Listen to tales of shrimp boats, wreckers, Civil War heroics, and learn the story behind the sinking of the US battleship Maine. For an hour and a half, this 49-passenger power catamaran will glide past Key West two institutions: the Key West Historic Seaport and Fort Zachary Taylor State Park. You’ll also see old Overseas Railways docks and Wisteria and Sunset Keys. The cruise departs from the Ocean Key Resort Marina at 4:30 p.m. and ends its journey by passing Mallory Square just as the sun hits the sea.

Stargazer Cruise aboard the Western Union Key West

This nightly cruise provides key lime ice cream or conch chowder for you to savor as Joe Universe, astronomer, narrates your 90-minute sail. Joe points out constellations, relates stories of their mythology, and answers questions. There’s also a slide presentation that helps you imagine the shapes that spring from each constellation, so you’ll actually see how a group of stars becomes an archer or a bear. Binoculars provided. The Full Moon Sail, a romantic 2-hour trip, replaces the Stargazer Cruise as appropriate both include complimentary champagne, wine, beer, and soda. The schooner also sails for sunset cruises and a day sail, during which you can apprentice as a deckhand while listening to a historical narration.

Reflections Big Pine Key

Reflections offers a variety of different kayak styles to suit every paddler (even kids), and is unique in that they’ll tow you to wherever the tides and winds make for the best eco-tour experience. Study marine life and tropical birds as you navigate shallow mangrove creeks or drift above sponge and coral beds submerged in clear, calm waters. No experience necessary; tours begin with a brief tutorial on kayaking and water safety. Eight people maximum per tour; three-hour guided tours operate twice daily, launching from various points in the Lower Keys. $50 per person.

The Glass Bottom Boat Marathon

Try your hand at “hookah diving,” which allows uncertified divers the chance to float through coral reef beds for two hours without surfacing, thanks to a surface-fed air hose. Of course, snorkeling and traditional scuba diving is also offered. The beautiful glass bottom boat reveals the ocean floor as you head to a few of the 40 reefs surrounding Marathon, motoring above stingrays, sharks, and hundreds of vibrantly colored tropical fish. Located on Grassy Key, MM 58.

Scarlet Ibis Tours Big Pine Key

Scarlet Ibis will drop you off nearly anywhere in the Big Pine area so you can explore the “true Florida Keys,” navigating mangroves and shallows in a stable v-bottom canoe. Different trips explore the Florida Keys National Marine Sanctuary, the National Key Deer Refuge, and the Great White Heron Refuge acreages. This outfitter also offers customized guided tours, including sunset and wilderness excursions, which are ideal for nature photographers and birdwatchers.

Airplane Tours

Seaplanes of Key West

Board a seaplane and see the sea from the sky. Sightseeing & snorkeling flights to Fort Jefferson and the Dry Tortugas run daily: half-day trips departs morning and afternoon and allows 2.5 hours on the Dry Tortugas, and full-day flights depart morning and provide 6.5 hours on the Tortugas. Snorkeling equipment and sodas are provided; please bring snacks but leave the dive gear on the main islands. During the forty-minute flight each way, relax in the cabin and watch porpoise, sharks, sea turtles, and stingray schools swim across the Atlantic and above long-wrecked ships. Children under 2 ride free; a refund or rescheduling is offered for cancellations due to inclement weather. Reservations are required.

Island Airplane Tours Key West

Test your nerves in a 1940s open-cockpit biplane piloted by a member of the “official air force of the Conch Republic.” If that doesn’t puch your limits, a ride in Island Airplane’s S2-B aerobatics airplane certainly will. Whether you choose a smooth ride or one wrought with twists & turns, you’ll see the islands and reefs like no one on the ground could. Sightseeing flights run between $50 and $200, depending on the aircraft and flight duration.

Tango One Flight Academy – Marathon Airport –

Tango One takes passengers around the landmarks of the Middle Keys: Bahia Honda’s beaches, the Sombrero Lighthouse & Reef, and the famous Seven Mile Bridge. The Cessna aircraft holds three passengers; reservations required.