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How to Spend a Perfect Day in Key West

Deborah Neyens is an attorney, educator, and freelance writer.

Key West sunset

Key West sunset

The island of Key West lies at the end of the Overseas Highway, a 127.5-mile stretch of U.S. Route 1 extending from Miami through the Florida Keys. Key West is the southernmost point of the continental United States (just 90 miles from Cuba), and its laidback, Caribbean vibe makes you feel like you've entered another country completely. Although locals declared independence from the United States in April 1982, more than 30 years later a large sign at the airport still welcomes travelers to the "Conch Republic." Rest assured there's no need to bring a passport or exchange money to come to this quaint and quirky island paradise.

Throughout the years, Key West has served as a refuge to all sorts: pirates, shipwreckers, smugglers, writers, artists, fishermen, musicians, and people simply looking for a change in latitude and a good time. With its colorful history and diverse culture, there's something for just about everyone in Key West. So much, in fact, that many a local taxi driver or bartender will be eager to tell you how they came to Key West for a visit and never left. But what if your time in Key West is limited? With this as your guide, you can immerse yourself in the carefree island milieu and get a taste of Key West's many flavors in just one day.

One of Key West's historic Old Town mansions

One of Key West's historic Old Town mansions

Another spectacular Key West sunset

Another spectacular Key West sunset

Lose the Car

Key West is only 2 miles wide by 4.5 miles long. It's small enough to navigate on foot and, with limited parking in such a compact area, it's best to leave the car behind as you explore the island. Bring a comfortable pair of walking shoes or, better yet, rent a bicycle for the day. There are numerous options for bike rentals all over the island and many hotels and inns provide bikes to their guests for a small rental fee or even free of charge.

Breakfast at Blue Heaven

Start your day with breakfast at this funky restaurant in Bahama Village, a colorful neighborhood of low pastel houses where you can buy giant cans of Old Milwaukee at the corner grocery if you so choose (and sometimes in Key West that seems like the thing to do). Blue Heaven is housed in a storied building where Ernest Hemingway once refereed Friday-night boxing matches. Get there early because the wait gets long. (In Key West time, early generally is any time before 10:00 am). Dining is al fresco and the roosters and chickens roaming the courtyard are friendly. Breakfast selections include shrimp and grits and the aptly-named Rooster Special, a basic two-egg breakfast with your choice of grits or potatoes and bacon or sausage. If it's on the menu, splurge on the Lobster Benedict. Don't miss the home-baked banana bread. (Thomas and Petronia, 729 Thomas Street, 305-296-8666, $15-$28)

A rooster struts among the diners at Blue Heaven

A rooster struts among the diners at Blue Heaven

Hit the Beach at Fort Zachary Taylor State Park

To wear off all that food, hop back on your bike and head over to Fort Zachary Taylor State Park to get some sun on the best beach in Key West. The park is accessed through Truman Annex at the end of Southard Street. Admission is $2 for pedestrians and bicyclists, and more for vehicles.

As you wind your way down the road, you will come to the Civil War-era fort on the right side of the road. There is a bike trail here that leads around the moat and another along the shipping channel. Watch for migratory birds in the tropical brush that stretches between the fort and the sea, especially during the winter and spring migration seasons. The beach is at the end of the road. Bikes are not allowed on the beach or in the pine-shaded picnic area, but there are plenty of bike racks. Beach chairs, umbrellas, and snorkel gear are available for rent at the concession stand.

If you don't want to lounge or swim, walk out to the west rock jetty and watch the boats coming and going through the entrance to the Key West Harbor, take a hike on the two short nature trails and get an up-close look at native vegetation, or explore the historic fort, which was an important Union outpost in the war between the states and later saw heavy use during the Spanish-American War. There are guided tours daily at noon and self-guided tours all day until 5:00.

Fort Zachary Taylor State Park

Fort Zachary Taylor State Park

On the beach

On the beach

Bone Island

Cayo Hueso (pronounced weso) was the island's original Spanish name, which translates to Bone Island. Legend has it that early explorers to the island found the beach littered with bones, said to be the remains of a Native American battlefield or burial ground.

The Cayo Hueso Café, on the beach, is open from 10:00 to 5:00 for a snack or light lunch (try a Cuban sandwich) once your breakfast wears off. (305-295-0037, $3–$7)

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Read more about Fort Zachary Taylor Historic State Park.

Tour Hemingway House

After you've had enough sun, head to the shaded grounds of the Hemingway House to get a glimpse of life in Key West in the thirties when Ernest Hemingway called the island his home. The literary legend lived in this Spanish Colonial-style mansion from 1931 to 1940 with his second wife Pauline and their two sons. Your enthusiastic and knowledgeable tour guide will share stories of Hemingway's escapades on the island and point out the architectural details and unique furnishings of the home. Make sure to ask about the urinal Hemingway drug all the way home after a drunken night at Sloppy Joe's to turn into a drinking fountain for his six-toed cats. The tour includes a stop at the writing studio where Hemingway penned such stories as The Snows of Kilimanjaro and For Whom the Bell Tolls during his most productive years as a writer. The house is open daily from 9:00 to 5:00. Admission is $12.50, which includes a 30-minute guided tour. (907 Whitehead Street, 305-294-1575)

Photo Opportunity at the Southernmost Point

No trip to Key West is complete without a stop at the concrete buoy marking the unofficial southernmost point in the continental United States. (The true southernmost point on the island is actually an unmarked spot on Navy land west of the buoy, but there is no civilian access.) To reach the marker, head to the south end of Whitehead Street at the corner of South Street. The throngs of tourists are thick here, especially when cruise ships are in port, so snap a quick photo and move on.

The author and her husband at Southernmost Point in February 2011

The author and her husband at Southernmost Point in February 2011

Sunset on the Afterdeck at Louie's Backyard

There are a lot of great places in Key West to watch the sun set over the Gulf of Mexico—the most famous being the spectacle that is the nightly sunset festival at Mallory Square—but I prefer the serenity of the Afterdeck Bar at Louie's Backyard. Louie's is housed in an oceanfront Victorian home that became a restaurant in 1971. Park your bike in the racks at the end of Vernon Street and cross the sand to get to the afterdeck behind the building. The wooden deck hangs out over the Atlantic Ocean, where you can enjoy the ocean breeze and a cocktail as the sky explodes into a million shades of coral at sunset. This is a favorite spot for locals and their dogs, and don't be surprised to see your favorite Key West bartenders and musicians relaxing here on their days off. The Afterdeck Bar is open from 11:30 am to 1:00 am every day but Christmas. (700 Waddell Avenue, 305-294-1061)

View from the Afterdeck Bar at sunset

View from the Afterdeck Bar at sunset

Dinner at the Historic Seaport

After the sun sinks below the horizon, head all the way over to the other side of the island for a fresh seafood dinner at Key West's Historic Seaport. There are numerous dining options just off the boardwalk lining the harbor. If you hurry, you may arrive in time to see the majestic wooden schooners Western Union and Appledore return to port from their nightly sunset cruises.

A great option for waterfront dining is the Half Shell Raw Bar, which is housed in an old shrimp packing building on the wharf at the end of Margaret Street. The atmosphere is casual to the extreme, with diners eating at picnic tables and old license plates covering the walls for a wacky patchwork quilt effect. You can't go wrong with selections from the raw bar, including gulf oysters on the half shell served with a six-pack of spicy condiments or the peel-and-eat shrimp. Don't miss the stone crab claws when in season (mid-October through mid-May). Entrees include fresh fish seafood selections like mahi-mahi and grouper cooked how you like them (broiled, grilled, fried or blackened) served with boiled red potatoes, corn on the cob, and coleslaw. End your meal with a slice of authentic key lime pie. (231 Margaret Street, 305-294-7496, $7-$23)

If you're looking for a more upscale dining experience, try A&B Lobster House. The romantic dining room offers picturesque harbor views and there's a large selection of wines to accompany the lobster and seafood specialties. Meat eaters will find several cuts of steak on the menu, as well as chicken and pork dishes. Start with the lobster bisque and try the hogfish or the fresh lobster pasta. For a real splurge, go with Berlin's surf and turf, a ten-ounce filet mignon and ten-ounce lobster tail. Split an order of bananas foster for an elegant end to the meal or head downstairs to Berlin's Martini & Cigar Bar for a cognac or dessert wine. (700 Front Street, 305-294-5880, $24-$69)

Before leaving the seaport, make sure to stop in at the Schooner Wharf Bar for a little slice of old Key West. The ramshackle bar's rustic nautical charm and laid-back atmosphere are conducive to striking up new friendships. Sip a rum runner or schooner vice (half piña colada, half strawberry daiquiri) as you enjoy live music and cool breezes off the harbor, and see why Schooner Wharf is called the best bar in Key West. (202 William Street, 305-292-3302)

A schooner returning from a sunset cruise

A schooner returning from a sunset cruise

The Duval Crawl

When the sun goes down, the party is just getting started in Key West. End your day with the world-famous Duval Street Crawl and check out the many bars and pubs lining Key West's legendary thoroughfare.

Perhaps the most iconic Key West drinking establishment is Sloppy Joe's Bar, which was Ernest Hemingway's favorite hangout. Indeed, it was Hemingway who encouraged his good friend and original owner Joe Russell to change the name of the establishment to Sloppy Joe's because the floor was always wet with melting ice. The bar moved to its current location at the corner of Duval and Greene Streets in 1937. It never closed during the move; patrons simply carried their drinks across the street to the new location and service continued without skipping a beat. Today, at least three bands take the large stage every day and the dance floor is usually crowded. The bar holds a Hemingway lookalike contest every July, an annual toga party in October during Fantasy Fest, and other special events throughout the year. When not in Key West, you can follow the fun remotely via multiple live webcams. (201 Duval Street)

How many friends can you squeeze into the World's Smallest Bar on Duval Street?

How many friends can you squeeze into the World's Smallest Bar on Duval Street?

The original Sloppy Joe's location is now the home of Captain Tony's Saloon, another Key West institution. The building has a colorful history, having been used at various times as an icehouse, a cigar factory, a bordello, and the city morgue. A tree growing up through the room and out the roof was once used to hang pirates and there are graves under the pool tables. Captain Tony Tarracino, a bootlegger as a boy who became a gun runner and, eventually, the mayor of Key West, bought the Key West landmark in 1958 and Captain Tony's Saloon was born. Until his death in November 2008 at the ripe old age of 92, Captain Tony could be found perched on his stool at the end of the bar signing autographs and flirting with the ladies. Captain Tony's Saloon offers live music seven days a week. (428 Greene Street)

Other notable stops on the Duval Crawl include:

  • Hog's Breath Saloon, with a back entrance on Duval Street (400 Front Street)
  • The World's Smallest Bar (124 Duval Street)
  • Irish Kevin's (211 Duval Street)
  • The Bull and Whistle Bar (224 Duval Street)
  • Jimmy Buffett's Margaritaville (500 Duval Street)
  • The Green Parrot Bar, located a block off Duval (601 Whitehead Street)


The author with Captain Tony just a few months before his death in 2008

The author with Captain Tony just a few months before his death in 2008

Where to Stay

Where should you go at the end of your perfect Key West day? There are numerous options for lodging on the island, ranging from small guesthouses to luxury resorts, but you can't beat the price or convenience of the Eden House Hotel.

Eden House is the oldest hotel in Key West and is centrally located in the heart of Old Town. The rooms are basic, yet clean and comfortable. The deluxe rooms are equipped with flat-screen TVs and refrigerators (many also have porches and swings), and you can upgrade to even larger suites with kitchenettes. The grounds feature a heated pool and hot tub, an elevated sundeck, and a grill area, and there are hammocks and waterfalls located throughout the tropical landscape for moments of pure relaxation. There is a restaurant on the property and a complimentary happy hour is held poolside daily. Other amenities include on-site bike rental, complimentary fruit and coffee in the morning, and a chilled drink waiting for you upon check-in.

Rates range from $115 to $385 per night during the off-season and $200 to $575 per night during the high season. (1015 Fleming Street, 305-296-6868 or 800-533-5397)

Eden House Hotel

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