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, 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. For information, call tel. 305/294-5161 or go to www.conchtourtrain.com. The cost is $29 for adults, $14 for children 4 to 12. Tickets are cheaper on the website. Daily departures are every half-hour from 9am to 4:30pm.
The Old Town Trolley 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. 305/296-6688 or visit www.trolleytours.com. Tours are $29 for adults, $14 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.
Whichever you choose, both of these historic, trivia-packed tours are well worth the price of tickets.
Proclaimed by the mayor as "the official air force of the Conch Republic," Island Aeroplane Tours, at Key West Airport, 3469 S. Roosevelt Blvd. (tel. 305/294-8687; www.keywestairtours.com), offers windy rides in its open-cockpit 1940 Waco biplanes that take you over the reefs and around the islands. Thrill-seekers will also enjoy a spin in the company's S2-B aerobatics airplane, which does loops, rolls, and sideways figure-eights. Company owner Fred Cabanas was decorated in 1991, after he spotted a Cuban airman defecting to the United States in a Russian-built MIG fighter. Sightseeing flights cost $90 to $345 for two people, depending on duration.
The catamarans and the glass-bottom boat of Fury Water Adventures, 237 Front St. (tel. 305/296-6293; www.furycat.com), depart on daytime coral-reef tours and evening sunset cruises (call for times). Reef trips cost $35 per person; sunset cruises are $37 per person. Kids ages 5 through 12 sail on all cruises for $19. Prices are cheaper on the website.
The schooner Western Union (tel. 305/292-9830; www.schoonerwesternunion.com) was built in 1939 and served as a cable-repair vessel until it was designated the flagship of the city of Key West and began day, sunset, and charter sailings. Sunset sailings are especially memorable and include entertainment, cocktails, and a cannon fire. Prices vary; inquire for details.
A new boat tour combines Florida Keys sunsets with delectable Keys cuisine. Sunset Culinaire Tours (tel. 305/296-0982; www.sunsetculinaire.com) is a cruise aboard the vessel RB's Lady and includes a tour of Key West harbor as the sun sinks below the horizon, and a three-course gourmet dinner (including beer or wine) prepared by Chef Brian Kirkpatrick. The vessel departs from Sunset Marina, off U.S. 1 at 5555 College Rd., at 5:30pm nightly. Boarding time is 5pm and the cost is $85 per person.
Sharon Wells (tel. 305/294-0566; www.kwlightgallery.com), historian, artist and owner of the KW Light Gallery, leads a slew of great tours throughout the island, focusing on things as diverse as literature, architecture, and places connected with the island's gay and lesbian culture.
For a lively look at Key West, try the Key West Pub Crawl (tel. 305/744-9804; www.keywestwalkingtours.com), a tour of the island's most famous bars. It's given on Tuesday and Friday nights at 8pm, lasts 2 1/2 hours, costs $30, and includes five (!) drinks. Another fun option is the 1-mile, 90-minute ghost tour (tel. 305/294-WALK ; www.hauntedtours.com), leaving daily at 8 and 9pm from the Holiday Inn La Concha, 430 Duval St. Cost is $15 for adults and $10 for children 11 and under. This spooky and interesting tour gives participants insight into many old island legends.
Key West's Ghosts and Legends Tour (tel. 866/622-4467 or 305/294-1713; www.keywestghosts.com) is a fun, 90-minute narrated tour of the island and spirits that don't come in a plastic cup or mug. You'll walk through the shadowy streets and lanes of Old Town, stopping at allegedly haunted Victorian mansions, and learning about fascinating island pirate lore, voodoo superstitions and rituals, a Count who lived with the corpse of his beloved, and other bizarre yet true aspects of this eerie place. Tours depart nightly from the Porter Mansion on the corner of Duval and Caroline streets. Space is limited and reservations are required. Tickets are $18 for adults and $10 for children.
Since the early 1940s, Key West has been a haven for gay luminaries such as Tennessee Williams and Broadway legend Jerry Herman. A trolley tour of Gay Key West, created by the Key West Business Guild, showcases the history, contributions, and landmarks associated with the island's flourishing gay and lesbian 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 and Angela streets. Look for the trolley with the rainbow flags. The cost is $20 to $25. Call tel. 305/294-4603 or go to www.gaykeywestfl.com.
Parrotheads on Parade
For Jimmy Buffett fans, or "parrotheads," as they're also known, Trails and Tales of Key West (tel. 305/292-2040) is an amusing, 2-hour guided walking tour in which Key West's finest storytellers share tales of Jimmy Buffett, Captain Tony, Ernest Hemingway, Mel Fisher, and more. The informative and often hilarious guides lead you past the hangouts and other high points of these colorful characters' Key West. Visit Buffett's first house on the island, Shrimp Boat Sound Recording Studio, where the likes of Toby Keith have since recorded. Visit legendary pubs and the historic seaport; plus, hear fascinating stories about the Conch Republic and get some insider tips to the secrets of Key West. This 2-hour tour departs daily at 4pm from Captain Tony's Saloon, 428 Greene St., where Buffett used to hang out and perform, and ends at -- you guessed it -- Margaritaville Cafe, on Duval Street. The tour conveniently goes during happy hour. Tickets are $20 for adults, and $10 for children 6 to 12. Bring cash or traveler's checks; no credit cards are accepted. Reservations are required.