Key West is unlike any place you’ve ever been. Sunsets are celebrated, roosters roam the streets, conch fritters are a recognized food group, drinking is an Olympic sport and everyone – and I do mean everyone – has a story. As one Key West resident told me, “This is where the weird go pro.”

Key West Harbor; Photo by Andy Newman/Florida Keys News Bureau

Everything about this place is quirky, even the Key West Cemetery. Located in the dead center of Old Town (Key West’s historic district) many of the historic whitewashed tombstones have unusual epitaphs. A hypochondriac’s tombstone reads “I told you I was sick.” A cheating husband is remembered by the headstone inscription his wife commissioned declaring, “At least I know where he’s sleeping tonight.” Amid the strangeness is the rather large plot of General Abraham Lincoln Sawyer, a 40 inch midget whose final wish was to be buried in a man-size tomb.

And then there’s Key West history. Texas may threaten to secede from the United States from time to time, but Key West actually did it. In April of 1982, the Keys declared itself the Conch Republic, named for the delicious shellfish Key West residents devour daily. The historic event was an act of protest against the U.S. Border Patrol when a blockade was set-up on US Highway 1, just north of the entrance into town outside of (believe it or not) Skeeter’s Last Chance Saloon. The roadblock was intended to stop illegal aliens from accessing the mainland, but the ensuing traffic jams resulted in a decline in tourism to the Keys and inevitable economic hardship.

Key West Southernmost Point- 90 miles to Cuba; Photo by Gregory Holder

Outraged at the isolation, “Skeeter” teamed up with Key West Mayor Dennis Wardlow and several determined residents. The group went to Federal court in Miami to seek an injunction to stop the blockade. When their plea was denied, the Mayor announced to the waiting television crews and reporters, “Tomorrow at noon the Florida Keys will secede from the Union!”

The next day, as promised, Mayor Wardlow stood in Mallory Square, read the proclamation of secession then ceremoniously whacked a federal agent over the head with a loaf of stale Cuban bread. The Conch Republic’s Civil Rebellion lasted approximately one minute and was followed by a surrender to the U.S. Navy Admiral in Key West but not before the Conchs blasted the Naval base with their water guns. To this day Key West residents have dual citizenship as Americans and Conchs. Newcomers to the island are granted a freshwater Conch status after seven years.

An excellent way to get acquainted with Key West’s colorful characters, history and unique attractions is aboard the World Famous Conch Train Tour. For over 50 years, Conch Train Tours have introduced visitors to Key West’s past with stories of pirates, Indians, visionaries, artists and literary legends like Ernest Hemingway who wrote many of his greatest works from his home in Key West surrounded by his six-toed cats.

Conch Train Tour; Photo by Gregory Holder

I joined the Conch Train Tour led by Mark, a musician originally from Philadelphia who has lived in Key West long enough to earn freshwater Conch status. As we rode through the streets of this charming town, Mark not only pointed out the tourist attractions, he told of over 150 little hidden lanes throughout Key West. Mark assured me exploration of these little hidden gems would yield secret gardens, mad parrots and undiscovered treasures. All tours are “hop on hop off” but I suggest riding the full route then venturing back to places of interest. You don’t want to miss the tall tales of Key West.

Besides its quirky characters, Key West has numerous intriguing attractions. The Key West Aquarium is unique with open tanks where nurse sharks swim just out of reach. There’s also a touch tank filled with starfish and other more mellow creatures of the sea. Climb the 88 steps to the top of the Key West lighthouse for a view of the island. When the lighthouse opened in 1848 its keeper was a woman – unheard of in the 19th century. A museum exhibits belongings, photographs and words of the lighthouse keepers and their families.

Key West Aquarium Touch Tank; Photo by Gregory Holder

Towering over the historic seaport, the Custom House Museum is a beautiful example of Richardsonian Romanesque architecture. Built in 1891, it was originally home to the island’s customs office, postal service and district courts. Today this national landmark is an award-winning museum with two floors of exhibits that weave together two centuries of history, art, people and events.

Stroll through a tropical paradise of flowering plants and trees, over 20 exotic bird species, and cascading waterfalls as you are surrounded by butterfly species from around the world at the Key West Butterfly & Nature Conservatory. Check out the Learning Center for an education about the anatomy, lifecycle and migratory world of the Monarch butterfly. View the spectacular creations of artist, Sam Trophia, in the Wings of Imagination Butterfly Gallery. For over 30 years, Sam has translated the butterfly world into an endless variety of compositions of natural color and beauty.

The main attraction in Key West is a natural one – the nightly sunsets. Crowds of tourists and locals gather at Mallory Square every evening for a Sunset Celebration. While you wait for the brilliant orange sun to sink into the sea, there are plenty of entertainers to keep you company. Browse arts and crafts booths, munch on conch fritters from the food carts or consult a psychic about your future. Street performers of every type abound. The tightrope walking cats are always a hit.

For a less crowded sunset viewing option, take to the water for a champagne sunset sail with Sebago’s Appledore. Board a schooner at the Historic Key West Seaport for a tour of the city’s harbor and surrounding waters. You’ll glide past Mallory Square to a front row seat for an awe inspiring Key West sunset with a glass of bubbly in hand.

After sunset Duval Street becomes party central. From upscale lounges to late night dancing and dive bars, Key West offers some of the best nightlife imaginable. Sip your favorite vino on the porch at the Grand Vin Wine Shop & Bar for great people watching. Enjoy a cocktail at the By George Piano Bar or The Cabaret at La Te Da. Rick’s & Durty Harry’s has all your options covered with a dance club, martini bar, frozen drinks, live music, adult entertainment and Karaoke. The iconic Green Parrot Bar features low prices and live music. Hog’s Breath Saloon offers great drinks, a tasty menu and the chance to call your friends with the Hog Webcam. You can also hang out at Ernest Hemingway’s old favorite, Sloppy Joes. Whatever your style, there is plenty of alcohol available to help you on your way to the Duval Crawl.


Tip from the TS Editorial Staff:

If you’re planning on a trip to the Miami and the Keys sometime soon, be sure to take advantage of the DK Eyewitness Travel Guide’s TOP 10 MIAMI & The Keys with almost a full 20 pages on the Keys.


The area code for Key West is 305.

Where to Stay:

Curry Mansion Inn – Built by Key West’s first millionaire, William Curry, the Curry Mansion Inn is located in historic Key West. The grand Victorian-style mansion is also an intriguing museum listed on the National Register of Historic Places. As a guest you will be treated to the finest amenities including a full deluxe breakfast, an afternoon open bar cocktail party and full access to the 22-room mansion.   The inn has received numerous accolades including the People’s Choice Award for Key West’s Favorite Guest House. And perhaps most important, Key Lime Pie was first created in the Curry Mansion kitchen by the Curry’s private cook, Aunt Sally. 511 Caroline Street, Key West, FL 33040; 800-253-3466. www.currymansion.com

Key Lime Pie

DoubleTree by Hilton Hotel Grand Key Resort – Located 1 mile from the beach and golf course in Key West, the Grand Key Resort offers an escape from the crowds and noise of Duval Street. The onsite pool features a waterfall, whirlpool, sunbathing decks and poolside massages. The poolside Tiki Bar is the perfect spot to sip a tropical beverage with one of those little umbrellas. When you are ready to sightsee or prowl about on Duval Street, the hotel’s complimentary shuttle service will drop you in the heart of old town. 3990 S. Roosevelt Blvd, Key West, FL 33040; 305-293-1818. www.doubletree.com

Where to Eat:

Blue Heaven – Through the years, the property has hosted cock fighting, gambling and Friday night boxing matches refereed by Ernest Hemingway. Renowned for its breakfast, Blue Heaven is also known for its laid-back Keys atmosphere where roosters roam the grounds while you dine. Indulge on classics like blueberry pancakes, shrimp & grits or Blue Heaven Benedicts. 729 Thomas Street, Key West, FL 33040; 305-296-8666. www.blueheavenkw.com

Photo by Gregory Holder

Resident Rooster; Photo by Gregory Holder

Conch Republic Seafood Restaurant – Dine on fresh fish and seafood and, of course, conch fritters while overlooking the Historic Seaport and Key West Marina. 631 Greene Street, Key West, FL 33040; 305-294-4403. www.conchrepublicseafood.com

Where to Drink:

Rick’s Bar – Rick’s Bar is the first, original bar of the entertainment complex’s eight. It is conveniently open seven days a week, offering live music every day, all day as well as midnight karaoke. 202 Duval Street, Key West, 33040; 305-296-5513. www.ricksbarkeywest.com

Sloppy Joe’s – Sloppy Joe’s offers a casual vibe with their no-reservations policy and late night hours. You can expect a show every night as well as their signature snacks, pizza, and desserts. 201 Duval Street, Key West, FL 33040; 305-294-5717. www.sloppyjoes.com

Hog’s Breath Saloon – Offers freshly smoked BBQ, seafood, live music, alcoholic beverages, a kid’s menu, as well as inside and outside dining options. 400 Front Street, Key West, FL 33040; 305-296-4222. www.hogsbreath.com/keywest

The Bars at La Te Da – The two bars at La Te Da, The Piano Bar and The Terrace Bar offer exceptional music and dining experiences, featuring musicians such as Debra and Patrick and Dave Bootle. 1125 Duval Street, Key West, Florida 33040; 877-528-3320. www.lateda.com

Grand Vin Wine Bar – The Grand Vin Wine Bar features a beautiful porch where guests can choose from a great selection of wines and specialty drinks.1107 Duval Street, Key West, FL 33040; 305-296-1020.

The Green Parrot Bar – This famous Key West dive prides itself for having no cover and no minimum charges as well as Monday night bingo and unique happy hour specials.

601 Whitehead Street, Key West, FL 33040; 305-294-6133. www.greenparrot.com

What to See & Do:

Sebago’s Appledore Cruises – Sip champagne and sail off into the sunset aboard a schooner. 205 Elizabeth Street, Unit 1, Key West, Florida 33040; 305-294-5687. www.keywestsebago.com

Key West Sunset; Photo by Gregory Holder

Key West Museum of Art & History – Explore Key West history at the Customs House Museum. 281 Front Street, Key West, Florida 33040; 305-295-6616. www.kwahs.org/visit/custom-house

Key West Lighthouse & Museum – Climb, explore and pay tribute to days gone by at the iconic Key West Lighthouse & Museum. 938 Whitehead Street, Key West, Florida 33040;

305-294-0012. www.kwahs.org/visit/lighthouse-keepers-quarters

The Key West Butterfly & Nature Conservatory – Surround yourself with butterflies and beauty. 1316 Duval Street, Key West, FL 33040; 305-296-2988. www.keywestbutterfly.com

Key West Aquarium – Connect with sea life at the Key West Aquarium’s Touch Tank. 1 Whitehead Street, Key West, FL 33040; 305-296-2051. www.keywestaquarium.com

Show more