Key West Tours By Tram & Trolley Bus

Yes, it’s more than a bit hokey to sit on this 60-foot tram of yellow cars, but it’s worth it—at least once. The city’s whole story is packed into a neat, 90-minute package on the Conch Tour Train (305/77-5775), which covers the island and all its rich, raunchy history. In operation since 1958, the cars are open-air, which can make the ride uncomfortable in bad weather. The engine of the “train” is a propane-powered jeep disguised as a locomotive. Tours depart from both Mallory Square and the Welcome Center, near where U.S. 1 becomes North Roosevelt Boulevard, on the less-developed side of the island. The cost ranges from $42 to $54 for adults, and is about $20 for children 12 and under. Tickets are cheaper on the website. Daily departures are every half-hour from 9am to 4:30pm.

The Old Town Trolley Tours (855/623-8289) is the choice in bad weather or if you’re staying at one of the hotels on its route. Humorous drivers maintain a running commentary as the enclosed trolley loops around the island’s streets past all the major sights. Trolley buses depart from Mallory Square and other points around the island, including many area hotels. For details, call [tel]  or visit . Tours are $52 to $70 for adults, and $20 for children 4 to 12. Tickets are cheaper on the website. Departures are daily every half-hour (though not always on the half-hour) from 9am to 4:30pm. Also from Old Town Trolley: Ghosts & Gravestones Frightseeing Tour, an hour of horrors as you look at Key West’s scariest sites and stories. Tours depart from 501 Front St. at 7pm, 8pm, 8:30pm, 9:30pm, and $10pm. Tickets range are $37 per person and children 12 and under are not recommended to attend. Call 305/294-4678 (it spells out GHOST) for more info.

Whichever you choose, both of these historic, trivia-packed tours are well worth the price of tickets.

Key West Tours By Air

Florida Keys Flight Academy, at Key West Airport, 3469 S. Roosevelt Blvd. (844/KEYS-AIR  [539-7247]), offers scenic airplane tours including one in a WWII trainer, a Vultee BT-13 Warbird.  Tours range from 20 minutes to an hour and all include the Seven Mile Bridge and assorted Key West landmarks. Prices range from $199 to $399 and most are for up to three passengers. They also do custom air tours.

Key West Tours By Bike

Besides walking, one of the best ways to explore Key West is by bike. With Key Lime Bike Tours, 122 Ann St. (305/340-7834), you can pedal around the Old Town district on a 2-hour bicycle tour led by a knowledgeable guide who will offer insight into everything from Key West’s seafaring history to architecture, foliage, and even local gossip. Included in the $45-per-person tour are a 25-ounce bottle of water, a slice of Key Lime Pie (work it off!), sunscreen, and ponchos. Tours are daily at 10am and 2pm. Bike rentals are $20 to $110.

Key West Tours By Boat

The catamarans and the glass-bottom boat of Fury Water Adventures, 237 Front St. (305/296-6293), depart on daytime coral-reef tours and evening sunset cruises. There are also jet ski tours, eco-tours, and parasailing. Prices are cheaper on the website, and range from $40 to $120 for adults and $20 to $100 for children 4-10.

The schooner Appledore Star (305/563-8157)  is the last known Chesapeake Bugeye ever built. its unique shallow draft design allows her to navigate Key West’s backcountry with ease on daily eco-tours exploring mangrove islands. In addition to the eco-tours, there’s a gorgeous champagne sunset sail, a Windjammer Day Sail, and, our personal fave, the Key West Bloody Mary Sail. Sails are two hours and range from $50 per adult and $25 for kids 4 to 11 and include alcoholic beverages, water and soft drinks. It’s a deal.

For shark sightings with a very colorful Key West flair, contact Capt. Ken Harris (305/508-1951), one of the area’s more famous captains known, along with relatives and fellow captains Dave and Clay Harris, as the Key West Shark Whisperers, working these docks for more than 30 years. See shark and wildlife on the 34-foot Tiger Cat, a custom-built eco-adventure catamaran, on which two-hour tours are $89 for adults, $49 for children 6 to 16, and $29 for children 5 and under.

Other Tours

Sharon Wells (305/923-5133;), historian and artist, leads a slew of great tours around the island, focusing on such diverse topics as literature, architecture, and places connected with the island’s LGBTQIA culture. Her Key West House tours are especially fascinating.

For a spirited take on Key West, try the Key West Pub Crawl (305/7998-8599), a tour of the island’s most famous bars. It’s given on Tuesday through Sunday nights at 8pm, lasts 2.5 hours, costs $34.95, and includes five (!) drinks. Another fun option is the 90-minute Bone Island Ghost Tour, leaving nightly at 8:30pm for $25. This spooky and interesting tour gives participants insight into many old island legends.

Ghosts and Gravestones of Key West (866/955-0668) is a fun, hour trolley tour of the island and spirits that don’t come in a plastic cup or mug. You’ll pass through the shadowy streets and lanes of Old Town, stopping at allegedly haunted Victorian mansions, and learning about island lore, superstitions and rituals, a scorned wife who haunted her ex, a cursed silver bar at the Key West Shipwreck Treasure Museum, haunted bars, and other bizarre yet true aspects of this eerie place. Tours depart nightly starting at 7pm with the last tour at 10pm from 501 Front Street. Tickets are $37.86 per person.

Since the early 1940s, Key West has been a haven for LGBTQIA+ luminaries such as Tennessee Williams and Broadway legend Jerry Herman. The Gay and Lesbian Historic Trolley Tour  showcases the history, contributions, and landmarks associated with the island’s flourishing LGBTQIA+ culture. Highlights include Williams’s house, the art gallery owned by Key West’s first gay mayor, and a variety of guesthouses whose gay owners fueled the island’s architectural-restoration movement. The 70-minute tour takes place Saturday at 10:50am, starting and ending at City of Key West parking lot, corner of Simonton Street and Angela Street. Look for the trolley with the rainbow flags. The cost is $20 to $25.

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.