Although you may believe Key West is about wasting away on margaritas, the island is more about celebrated history than revelry. You will, however, have to engage in both to appreciate the special character, and characters, of this place.
If you don’t have wheels, it’s no problem here. The City of Key West Department of Transportation (305-600-1455) has automated public transit service listings and you can visit the map to access functions online. It’s an efficient service for only a few bucks. The green and blue routes go almost everywhere, including the airport, shopping centers, Garrison Bight and Stock Island. There also is shuttle service as far north as Marathon.
Another transportation option is FreeBee (https://ridefreebee.com), a complimentary, on-demand, electric transportation service available seven days a week. Download their app, set up a pick-up spot, select your destination and enjoy the ride. Their free service covers all of Stock Island and Key West, except for the airport, from 5 a.m. until 9 p.m.
You can also hop aboard the Conch Tour Train (303 Front St.; 305-707-5775) or the Old Town Trolley (1 Whitehead St.; 855-623-8289). These guided tours ramble past the historic seaport, infamous drinking establishments and the lovely homes and gardens showing Bahamian, Cuban and New England influences in their architecture.

For sheer fun, the ritualistic celebration of sunset at Mallory Square is street theater at its finest. On any day, you may see a sword swallower, a mystic who walks on coals, dancing dogs and amazing cats, a fearless chain saw juggler, and other unconventional performers. It all happens on the quay as the sun is setting and a green flash may or may not blink just over the horizon. The nightly gathering includes booths for artists, craftsmen and food vendors. Mallory Square, named after native son Stephen R. Mallory, secretary of the Confederate Navy, was a prosperous wrecking center in the 1800s. The old chandlery now houses the Chamber of Commerce (510 Greene St.; 305-294-2587), where you’ll find brochures on attractions, entertainment and restaurants.
When visiting Mallory Square, check out the Museum of Art and History at the Custom House (281 Front St.; 305-295-6616). This imposing, Romanesque-revival structure was at various times a post office, Navy and Coast Guard center, district court, and court of inquiry during the investigation of the USS Maine sinking in Havana, Cuba.
Sunken ships were the livelihood of Key Westers in the early days, yet it was Mel Fisher who came up with the biggest booty in the 1980s. More than 350 years after several Spanish galleons sank in the Florida Straits, Fisher discovered the remains of the Nuestra Señora de Atocha and Santa Margarita off the Marquesas. It took nearly 20 years of scanning 100,000 square miles of ocean before he came across this sunken Fort Knox, valued at hundreds of millions of dollars. Find the treasure for yourself at the Mel Fisher Maritime Museum (200 Greene St.; 305-294-2633), less than two blocks from Mallory Square.
If you treasure the undersea environment and the creatures that live there, check out Reef Relief (631 Greene St.; 305-294-3100) at the historic seaport in the Waterfront Market building. Its efforts include installing mooring buoys near the reefs so we all can enjoy the coral without doing damage. Visitors are welcome from Labor Day through Memorial Day, but the center runs a “Coral Camp” for kids ages six through 12 during summer. The camp introduces kids to the fun of conducting science projects and takes them out to the reefs where they can snorkel. Both locals and visitors are welcome to sign up their kids for the weekday sessions. Call for details.
You can dredge up memories of the wrecking era at the Key West Shipwreck Treasures Museum (1 Whitehead St.; 305-292-8990), where actors portray the seafarers who heeded the cry, “Wreck ashore!” You can also dive into Key West Aquarium (1 Whitehead St.; 305-910-2791) at the same address for an up-close look at sea turtles, stingrays and sharks. If you’ve read closely, you’ll see these two spots share the same address — even though they are across the street from each other. Like “Keys time,” addresses around these parts can take a little getting used to.

Pop over to the Ernest Hemingway Home and Museum (907 Whitehead St.; 305-294-1136), once the home of “Papa.” Today, it’s a cathouse where you’ll find a colony of six-toed felines guarding the grounds. While living here, the legendary Hemingway wrote in the morning, fished in the afternoon and caroused at night. The museum is open 365 days a year from 9 a.m. until 5 p.m.
Hemingway’s hobby was fishing, and the charter captains here can satisfy anyone’s angling passion. Most marinas offer deep-sea or backcountry trips. The biggest fleets are located at Key West Bight Marina (201 William St.; 305-809-3984) and Historic Charter Boat Row (1801 N Roosevelt Blvd; 305-423-2384) at City Marina at Garrison Bight (1801 N Roosevelt Blvd; 305-809-3981), where you’ll find 30-plus captains ready to show you a fun day on the water.
You can catch up on military history at the Fort Zachary Taylor Historic State Park (601 Howard England Way; 305-292-6713), named after the 12th U.S. president. Begun in 1845, the brick fort took more than 20 years to build and was active during the Civil War, the Spanish-American War and both world wars. If your interests are more suntan-inspired, there’s a beautiful beach next to the fort that will keep you occupied while others in your group tour the facility. Visitors can also enjoy a short nature trail and bicycling path here.
If you haven’t had your fill of fish by this point, drop in at the Florida Keys Eco Discovery Center (35 Quay Rd.; 305-809-4750). It is across the street from Fort Zachary Taylor Historic State Park and admission is free.
The 44-acre former Truman Annex Naval Station was auctioned in 1986 for $17 million to a New England developer. Most of the significant historic structures at the annex have been rehabilitated, including the Little White House (111 Front St.; 305-509-6139). Built in 1890 as the commandant’s quarters, the house evolved into the base VIP lodge. While several presidents all visited Key West, only Harry S. Truman stayed overnight in the building. His casual demeanor and gaudy tropical shirts endeared him to the citizenry.
For the ultimate in kitsch, head southeast of the Annex to the end of Whitehead Street, the southernmost point in the continental United States — allegedly. (The true southernmost point is Ballast Key, 10 miles to the southwest.) Have your photo taken in front of the large concrete buoy that’s painted black, white, red and yellow. This is undoubtedly the most photographed attraction in all the Keys.
For a week in January and February, The Southernmost Regatta, which has effectively replaced the long-running Key West Race Week, attracts top sailors from around the world to compete in some of the country’s best sailing conditions. You can watch the sailors on the race course during the day and rub elbows with them at night.
For speed of another kind, the Race World Offshore World Championship is held in the fall. Moving at a much slower pace, the Hemingway Days festival fills in the lazy, hazy days of summer each July. Don’t miss the Ernest Hemingway lookalike contest, along with book signings by authors of interest.
The Conchs commemorate the Conch Republic Independence Celebration in April to mark their secession from Florida in 1982 (unofficial motto: “We seceded where others failed”). December brings the Lighted Boat Parade, but the ultimate crazy Conch experience comes with Halloween’s Fantasy Fest. It’s so bawdy that we can’t publish pictures of it here.