Key West is tiny but packed with things to do — here 11 activities that locals say you can't miss, from boozy Tiki cruises to spooky ghost tours
- As a Florida local, Key West is one of my favorite places because there's always something to do.
- Here are my top 11 activities to do there, from the best museums to where to go bar-hopping.
Although Key West isn't very large, at about four square miles in area, it's jam-packed with attractions. From quirky museums and historic homes to world-class dining and mind-blowing sunsets, there's plenty to keep you occupied.
And did I mention the water? Whether you're lounging on a beach or taking to the turquoise waters via kayak, stand-up paddleboard, motorboat, or Jet Ski, there's water, water everywhere in Key West.
This diversity of attractions within a manageable area makes it a popular destination for families, couples, and singles alike. I've been there for bachelorette parties, my wedding anniversary, and a family reunion. While many of the attractions are tried-and-true, there's always something new to discover, too.
Based on 20 years of visiting the island, this is a bucket list for just about anyone visiting Key West.
Sunset cruise
Key West's sunsets are legendary — and for good reason. When you're located at the western end of an archipelago, there's nothing in the way to block the view. While celebrating the sunset at Mallory Square is a must, experiencing it on the water is even better.
Many tour operators in Key West offer sunset cruises on a variety of ships, including pontoons, catamarans, and sailboats. Some of the larger vessels are less expensive, but they can get pretty packed with visitors.
If you can afford it and want a more intimate experience, I suggest a smaller ship, like the sailboat my husband and I went on during our first anniversary trip to Key West. It's not a private charter, but we prefer the smaller group size. Our two-hour ride on Key West Schooners' Appledore, which moors in the historic seaport and accommodates no more than 22 passengers, included adult beverages and appetizers. As the sky turned shades of pink and orange above the shimmering waters, the view was picture-postcard perfect.
Ghost tour
Considering its cemetery has headstones with epitaphs like "I told you I was sick" and "I'm just resting my eyes," it's not surprising that Key West has some spine-chilling ghost tours. (The cemetery itself is open to the public and worth a visit if you're into that kind of thing.) In fact, the island was originally called Bone Key because human bones were found along its shore.
Even if you don't believe in ghosts, take a nocturnal tour of the island's oldest buildings for a bit of history and a dash of chills. Key West's colorful past includes a motley crue of smugglers, presidents, foreign merchants, writers, pirates, and artists.
While I'm a bit of a cynic when it comes to the supernatural, I had a blast on the popular Ghosts & Gravestones tour. The one-hour trolley ride was just the right length, and our costumed guide was both funny and knowledgeable about the island's history. She even had a "ghost meter," which kids on the tour loved.
Photos at Southernmost Point
One of the most photographed attractions in the country is the Southernmost Point Buoy, which marks the point of lowest latitude in the contiguous US. Located at the corner of South Street and Whitehead Street, the colorful concrete monument was erected in 1983 and has endured several hurricanes in the years since. It's located just 18 feet above sea level and about 90 miles north of Cuba.
Yes, you'll be jockeying for position with other visitors to get a selfie with the buoy, which is open 24 hours a day, 365 days a year. To beat the lines, try visiting early in the morning or at sunset, when most visitors are gathered in or around Mallory Square for the best views.
Cruisin' Tikis Key West
The slogan of Cruisin' Tikis Key West is "Why go bar hopping when you can hop on a bar?" And I can't argue with that logic. It combines the best of land and sea. On this floating, motorized Tiki bar, your host plays double duty as captain and bartender as you and five other passengers enjoy a morning or sunset tour.
Note that it's BYOB: The tiki boat provides coolers, water, sodas, and cups, so bring your favorite adult beverages, and let the good times roll. You can even blast your choice of tunes on the Bluetooth radio. (May we suggest the Radio Margaritaville channel on SiriusXM?)
Your best bet is the 120-minute sunset cruise, gliding past the historic seaport, Sunset Pier, and Mallory Square en route to your front-row seat for the main attraction: the sunset. Keep an eye out for the green flash, a rare phenomenon in which a burst of green light appears just as the sun slips below the horizon.
Shop locally made goods
Take it from this shopaholic: Although Duval Street is lined with souvenir shops hawking cheap T-shirts, there's good shopping to be found in Key West. You just need to know where to look.
One of the most popular retailers on the island is Kino Sandals, where Cuban immigrant Roberto "Kino" Lopez and his family have been handcrafting affordable footwear since 1966. Other goods handmade on the island can be found at Key West Pottery, where Adam Russell and Kelly Lever create functional vessels as well as fine-art pieces with a modern take on the coastal aesthetic. The coffee mug I bought there is my go-to.
Of course, you'll find Key lime-flavored everything throughout Key West — think hot sauces, hard candies, fudge, and even wines — but my favorite is the frozen Key lime pie on a stick, dipped in chocolate. Several shops sell these, but Kermit's Key West Key Lime Shoppe makes some of the best. Wash down your snacks by sampling locally produced spirits at Key West's First Legal Rum Distillery or Papa's Pilar Rum Distillery.
Finally, the Key West Artisan Market at Higgs Beach, open from November to April, features books by local authors, original art, handmade jewelry, and more.
Audubon House and Tropical Garden
Equal parts historic home, gallery, and botanical garden, the Audubon House and Tropical Garden wasn't the residence of the famed bird painter John James Audubon. He did work at the home, though, which was built in the 1840s and has been historically restored and preserved.
Located in Old Town, the two-story house is in the American classic revival style, complete with lime-green shutters and spacious porches. Walking inside is like stepping into a time warp, thanks to the period-specific furniture, dishes, and clothing, while some of Audubon's original lithographs and watercolors grace the walls.
Outside, guests can stroll through the lush botanical gardens, admiring the koi pond and historic outdoor kitchen, and pursue the Audubon House Gallery. If you're tempted to purchase one of the limited-edition works by Audubon, framing services are available on site.
Mallory Square Sunset Celebration
Every night is a party at Mallory Square, a waterfront plaza near the end of Duval Street on the northwest corner of the island. Since much of the island's waterfront is occupied by resorts, this is a prime spot for the public to gather for Key West's legendary sunsets and the Mallory Square Sunset Celebration.
About two hours before sunset, street performers, musicians, and artists set up shop. (Don't miss Dominique the Cat Man and his feline circus.) Vendors at small booths and carts offer artisanal crafts and refreshments, like Key limeade. You can even get a tarot-card reading. While touristy, the vibe is laid-back, funky, and truly one of a kind.
If you want to cheers the sunset with your fellow revelers, I recommend buying a drink before you get to the square. While there are drink vendors onsite, the prices are high and the lines long.
Harry S. Truman Little White House
Despite its name, the Harry S. Truman Little White House has hosted six presidents — William Taft, Dwight Eisenhower, John Kennedy, Jimmy Carter, and Bill Clinton — not just the 33rd. But Truman spent the most time there — 175 days of his presidency — after doctors advised him to relocate to a warmer climate for his health. While he attended to serious matters during his time there, like the Marshall Plan and the Truman Doctrine, he had his share of fun, too, hosting fishing trips and playing poker with Cabinet members.
His custom-made poker table is among original furniture on view at the Little White House, alongside exhibits on the life and times of the president who decided to drop the atomic bomb. History buffs won't want to pass up the guided tour of Florida's only presidential museum, which was built in 1890.
During my first visit, I almost left without checking out the onsite botanical gardens until a guide pointed them out. Enclosed by the original wrought-iron fence from 1890, the one-acre garden is currently being restored to the way it looked in 1949.
Hemingway Home and Museum
While waiting on a car being delivered from Cuba, Ernest Hemingway (aka Papa) was stuck on Key West for a few weeks. Although he was eager to leave at first, he fell in love with the island, living there from 1928 to 1939.
Built in 1951, the Hemingway Home and Museum is where he lived for the majority of his stay in Key West, and, today, it serves as a monument to the legendary writer and renaissance man. The Spanish colonial house stands out among the Key West-style homes on the island, boasting bright-yellow shutters, plentiful arched windows, and ornate wrought-iron railings on its second-floor wraparound balcony.
The Spanish theme continues inside, where much of Hemingway's collection of 17th- and 18th-century furniture remains. While other highlights include Papa's writing studio, the 80,784-gallon pool, and urinal from Sloppy Joe's bar, the estate may be best known for its polydactyl (six-toed) cats.
The felines, which descended from Snow White, Hemingway's six-toed pet, roam freely throughout the property. The author named his cats after famous people of the time, like Tennessee Williams and Clark Gable, and that tradition continues today. To learn more about the famed felines, download the Hemingway Cats app.
Bar-hop Duval Street
Akin to New Orleans' Bourbon Street, Duval Street is the main drag in Key West's Old Town. By day, tourists shop for souvenirs and eat ice cream; by night, drunken revelers order beers and groove to live music.
While touristy, bar-hopping down and around Duval Street is a must, where the famous bars serve shots with a chaser of history. For example, everyone knows that Sloppy Joe's is a Key West landmark. But what they might not know is that the original Sloppy Joe's was located where Capt. Tony's Saloon is today. Claiming to be the oldest bar in Florida, its list of famous patrons includes Williams, Truman Capote, and Hemingway, who met his third wife there.
Other options I recommend on and around Duval include Flying Monkeys Saloon for 20 frozen drink varieties; Hog's Breath Saloon for live music, including nationally known bands; Irish Kevin's for a classic pub setting and Irish fare; Mary Ellen's Bar for the drunken spelling bee; and Two Friends Patio for their famous Bloody Marys. If you're feeling bold, check out Garden of Eden, a clothing-optional adventure on a rooftop above the Bull & Whistle bar. (I wore a bikini top and shorts. That was the extent of my foray into exhibitionism.)
Keep in mind that a lot of Key West's famous (or infamous) watering holes are dive bars. But that's part of the charm.
Dry Tortugas National Park
Yes, you'll invest most of a day on an excursion to Dry Tortugas National Park, but it's well worth the trip — and many visitors have no clue it's there. About a 2.5-hour boat ride (or 70 miles) from Key West, the Dry Tortugas is a group of seven keys surrounded by crystalline water. They're located along a major shipping channel and thus have a colorful history of Spanish explorers and merchants plying the waters there.
Today, visitors can visit the historic Fort Jefferson, which was built between 1846 and 1875 to guard the United States' gateway to the Gulf of Mexico. The park is also lauded for its excellent diving and snorkeling opportunities, including the Little Africa reef, known for its large coral formations, and the Windjammer shipwreck.
But you'll have to pay to get there, and make sure to book in advance. Options for reaching Dry Tortugas include charters from private tour operators as well as the popular Yankee Freedom ferry. The ticket price for the latter includes breakfast and lunch, snorkeling equipment, a narrated tour of the fort, and the park entry fee.
Based on my visits there, I suggest going between November and April as the winds aren't as strong during this time of year, making for calmer waters — which divers and seasick-prone ferry passengers will appreciate.
View Insider's comprehensive guide to visiting Key West, Florida.