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Historical and cultural travel experiences

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Key West and the Florida Keys: A Historic Getaway for the Curious Traveler

Hemingway house & museum, Key West

The Florida Keys have long been a magnet for adventure seekers, beach bums, artists, and history lovers alike — and nowhere encapsulates this sun-drenched magic better than Key West. If your idea of a perfect vacation includes learning something new while enjoying ocean breezes and cold drinks, then you’re in for a treat. From 19th-century forts to literary landmarks, Key West is packed with historic treasures waiting to be explored.

And let’s be clear: this isn’t your average dusty-museum kind of history. This is vibrant, eccentric, rum-soaked, and unapologetically oddball storytelling brought to life in pastel colors and tropical flair. While you’re hopping between historic stops, you’ll also want to experience the island’s famously fresh seafood and perhaps even cast a fishing line of your own.

Step into the Past at Fort Zachary Taylor

Let’s start with a heavy hitter: Fort Zachary Taylor Historic State Park, a Civil War-era fort built in the mid-1800s. This fortress of red bricks once protected the southern coastline and played a key role in both the Civil War and Spanish-American War. Wander through its winding corridors, climb up the old walls, and take in panoramic views of the turquoise waters below. Then walk down to the beach for a swim or a quiet nap under the pines. It’s a blend of history and nature you won’t want to miss.

Ernest Hemingway Home & Museum

No trip to Key West would be complete without a visit to the Ernest Hemingway Home and Museum. The legendary writer lived and wrote here during the 1930s, and the Spanish colonial house remains nearly unchanged. You’ll meet dozens of six-toed cats (descendants of Hemingway’s own pets), wander through his lush gardens, and step inside the writing studio where he crafted some of his most famous works. Whether you’re a fan of literature or just enjoy a good story, the Hemingway House is a Key West icon.

Harry S. Truman’s Little White House

Presidential history lovers, take note: Harry S. Truman’s Little White House served as the winter getaway for America’s 33rd president. It’s now a museum where visitors can see the rooms exactly as they were when Truman came down to escape D.C. winters. The site also hosted Eisenhower, Kennedy, and even Bill Clinton. Guided tours reveal not just the political backdrop, but also the personal quirks of a president who played poker and walked the streets like a local.

A Taste of the Sea at Eaton Street

Between historic landmarks, you’ll definitely work up an appetite — and there’s no better place to refuel than Eaton Street Seafood Market. Housed in a lovingly preserved Art Deco building just steps from the Seaport, this local favorite serves up grilled lobster tails, golden crab cakes, and their signature Key West pink shrimp.

Grab a spot at one of the shaded outdoor tables and watch the world go by as you dig into the freshest catch in town. Eaton Street’s seafood is so good, you’ll want to bring some home with you. You can check out their selection of shrimp and have it shipped anywhere in the continental U.S. — a perfect way to extend your island flavor long after your trip ends.

Dive into Local Lore at the Key West Cemetery

Now, this may sound morbid, but trust us: the Key West Cemetery is a must-see. Established in 1847, it’s full of quirky epitaphs, unique architecture, and some true Conch history. Notable residents include sailors, cigar makers, and even a legendary Bahamian voodoo priestess. Don’t miss the famous gravestone that reads, “I told you I was sick.” This is history with a side of island humor.

Custom Fishing Adventures with Seize the Day Charters

Looking to experience Key West the way early settlers and seafarers once did? Get out on the water with Seize the Day Charters. Captain Russ offers personalized fishing trips for all experience levels — from calm inshore waters to deep-sea excursions. You’ll not only enjoy the thrill of the catch, but you’ll also learn about the maritime history of the Keys from a true local expert. Read more about Seize the Day Charters and plan a trip that’s equal parts adventure and education.

Visit the Custom House and Mel Fisher Museum

For those who like their history with a touch of treasure, don’t miss the Mel Fisher Maritime Museum. This fascinating spot tells the story of Fisher’s discovery of the Spanish galleon Nuestra Señora de Atocha, which sank in 1622. The museum is home to gold bars, antique navigational tools, and actual artifacts pulled from the depths of the ocean.

Nearby, the Custom House Museum — with its towering red brick façade — offers rotating exhibits on Key West’s art, politics, and quirky past. Stand on the balcony and imagine the arrival of cigar ships from Cuba and the bustling port town Key West once was.

Soak It All In

What makes Key West special is its layered identity — equal parts paradise, pirate port, presidential retreat, and artist’s muse. Around every corner is a plaque, a statue, or an old building with a story that seems stranger and more delightful than the last. It’s the kind of place where history isn’t just preserved — it’s celebrated with a wink and a margarita.

Whether you’re exploring forts, fishing the reef, or enjoying a fresh seafood meal in a historic building, Key West offers a one-of-a-kind blend of the old and the unforgettable. So pack your sunscreen and your curiosity — and prepare to fall in love with a city where the past is never too far behind. Don’t forget to check out TripAdvisor to save and compare your travel accommodations!

 

Tagged With: Key West attractions Filed Under: North America Travel

Retracing the Footsteps of Ernest Hemingway

Hemingway Museum

Key West Florida

by Edward Quan 

With a reputation as a womanizer, a heavy drinker, all while pursuing high adventure such as big game hunting in Africa, Ernest Hemingway was one of America’s greatest novelists during the 20th century. He was also a highly disciplined writer who even after a long night of drinking, would rise at seven every morning to his private studio above his garage. This is where he composed some of his greatest literary novels, resulting in winning the Pulitzer Prize for Literature.

My journey to experience more of Hemingway’s legendary life began with a flight to sun filled Miami, home to some of the most beautiful white sand beaches in America. It’s a four-hour drive across the majestic Florida Keys islands to The Ernest Hemingway Home and Museum, located in Old Town district of Key West Florida, the farthest southern point in the continental United States. It’s a small island community surrounded by the turquoise waters of the Caribbean where you can actually view Cuba, which is only 90 miles away.

Photo of HemingwayIn 1928, Ernest Hemingway arrived at this tranquil island haven from Paris with his second wife, Pauline Pfeiffer, an accomplished journalist and contributor to Vogue Paris fashion magazine. The residence was a wedding gift from Pauline’s wealthy uncle Gus Pfeiffer, given to them in 1931.

Built in a Spanish Colonial style, this two-story residence stands in grandeur painted in white with mustard color shutters, framing its large bay windows. Above, roof covered balconies surround the upstairs bedrooms offering a quiet sanctuary from hot summer days. Lush green gardens filled with colorful flowers surround the property, like a rich tropical oasis. It was and still is the largest residential property on the island of Key West. Located across the street from the front gate is the Key West lighthouse, which opened in 1848. This six and one-half story tall white tower was an important landmark for Hemingway personally, as it helped him find his way home after each night of drinking.

Pauline Pfeiffer photoAs I toured the house, you are immersed with Hemingway’s remarkable literary achievements. Each bedroom commemorates one of his great novels. The rooms are filled with personal mementos such as European hand carved antique furniture, life size trophy heads and animal skins from his African’s safaris and hunting trips from across the American west. He drew his inspiration for his boundless writings from many of these treasures.

Across from the main house and high above the garage Hemingway’s private studio features an old manual typewriter on a rich mahogany table, paired with a sturdy leather-covered chair. The walls are covered with more of his personal hunting trophies. Shelves filled with his hardcover books sit between the floor to ceiling bay windows. You can sense Hemingway’s true discipline as a writer when entering his studio; everything seems to have its place.

Hemingway's studioThe most lavish feature of his residence is the 60 foot long, 24 foot wide, 10 foot deep in-ground aqua blue colored swimming pool, carved from the same solid coral bedrock which Key West Island sits upon. In the 1930’s, no one had a swimming pool, as there was no fresh running water on the island. Therefore, the 80,000-gallon lighted swimming pool had to be filled by drilling down to the salt-water table and pumping the water into the pool. Filling the pool took nearly three days and during the summer months, salt water would only stay fresh for a few days. As a result, each week the pool had to be drained, the pool surfaces cleaned of algae, and then refilled again.

The cost of building the swimming pool was US$20,000, which was outlandish considering that Gus Pfeiffer only paid US$8,000 for the entire property. Hemingway is the one who proposed building the pool, yet he complained bitterly to Pauline about its high expense during construction. Our tour guide shared with us a story of Hemingway throwing down a penny at Pauline’s feet on the pool patio shouting, “Pauline, you’ve spend all but my last penny, so you might as well have that!” As Hemingway’s novels were rewritten as screenplays for motion pictures, Hollywood producers and movie stars were calling and Pauline was determined to host the most extravagant poolside parties on the island. Today, you can view a penny embedded in the concrete pool patio, which memorializes Hemingway’s lost battle with his wife.

Polydactyl catAs I explored the residence grounds I came across several cats, all named after Hollywood stars from the 1930’s such as Humphrey Bogart and Ingrid Bergman. Hemingway’s household included a six-toed white cat named Snow White, which was given to him by a ship captain. Sailors considered these unique cats to be good luck, as they were very effective at catching vermin on board ships. Today, the only residences of The Hemingway Home and Museum are 47 polydactyl (six-toed) cats and it is believed that Snow White descendants live on the grounds today. Your average household cat has five front toes and four back toes. With the polydactyl gene in their DNA, that allows them to produce six-toed off spring.

Unsurprisingly, Ernest and Pauline Hemingway divorced in 1940 resulting in Ernest moving to his summer house in Cuba with fellow correspondent Martha Gellhorn, soon to be wife number three, for the next chapter of his dramatic life.

The Hemingway House and Museum gives you a unique window into the influence and legacy of one of the greatest writers of our time. It is well worth a visit during your next trip to Florida.

 


Key West Ultimate Island Experience

If You Go:

♦ The Hemingway Home & Museum 907 Whitehead St. Key West, Florida. Guided tours available. Hours: 9 am – 5 pm, open every day including holidays.

♦ Key West has an airport, cruise ship terminal and is the start of US Highway 1. Rent a vehicle in Miami and experience one of my top ten US scenic drives; Highway 1, a 113-mile drive over 42 magnificent bridges across Florida’s Keys coral islands. Majority of the highway is only two lanes; allow up to four hours driving time from Miami.

♦ Caribbean hurricane season is from summer to fall, recommend the winter months to avoid rainy days.

♦ Truman Hotel, a trendy boutique hotel in the heart of Key West. Easy walking distance to Hemingway’s House & Museum and Duval Street with restaurants, bars and shopping.

♦ Two local flavors that you must experience when visiting Key West. Crispy conch fritters, a large shelled sea creature and key lime pie made from locally grown limes. No visit would be complete without a visit to Jimmy Buffett’s Margaritaville restaurant on Duval St. for drinks and souvenirs.


Key West Pub Crawl

About the author:
Edward Quan is a fashion and travel writer with a background as a European luxury fashion buyer. He lives and breathes the world of high fashion. From the style capitals across the globe, he shares their influences on designer fashion from art and culture, music and cinema, to history and architecture. Writing exceptional stories on personal style while traveling well, featuring the latest news on the fashion scene, luxury hotels and resorts, fine food and wine and of course, shopping. Learn more about Edward Quan by visiting his fashion column Style Drama that appears in The Bahamas Weekly In addition, he is a guest journalist with Retail-Insider, and member of the BC Association of Travel Writers.

All photos are by LM Quan:
The Ernest Hemingway Home and Museum in Old Town district of Key West, Florida.
One of the many photos on display that chronicles Ernest Hemingway’s life and times during his nine years in the Florida Keys.
Pauline, Ernest Hemmingway’s second wife, pursued a luxurious Hollywood lifestyle with extravagant poolside parties.
Ernest Hemingway studio resides above his garage with his desk and manual typewriter surrounded by his personal mementos.
One of 47 polydactyl (six-toed) cats that reside at the Ernest Hemingway House and Museum.

Tagged With: Florida travel, Key West attractions Filed Under: North America Travel

Key West, Florida

 

Key West pier at Sunset

Where Pictures Speak More Than A Thousand Words

by Roy A. Barnes

tourists and locals in Key West, FLKey West, Florida, has come a long way from its days in the earlier 20th century when novelist Thelma Strabel wrote in 1940, “There is nothing for restless people to do. It is quiet and careless and charming.” I found the Spring Break hotspot to be one of the country’s most touristy places on the surface. Yet here, amidst all the sailboats, warm and breezy tropical conditions, outdoor cafes lining the city’s main drag called Duvall Street where the words “I’ll have Key Lime Pie” is uttered over and over, I found a place where its quirky aspects make it a memorable . For those things that reflect the culture, traditions, and unique flavors resonate more with me than the typical tourist quest to find “Margaritaville.”

Why did the Key West Chickens cross the road?

chickens on Key West sidewalkI soon found out while walking in Old Town that one doesn’t just share sidewalks with droves of locals and tourists wearing short shorts, but many other two-footed creatures who have ditched any clothes altogether: chickens. While these fowl have been around for almost two centuries, their numbers especially grew in the 1950s after Cubans fleeing Cuba brought them for use in cock fighting, food, and eggs. Their numbers multiplied over time after cock fighting was outlawed and grocery stores provided easier access to eggs and poultry. The roosters don’t just crow with the sunrise either as I found out at 230 a.m. in my hotel room. Nonetheless, there’s what seems to be an uneasy tolerance for the chickens’ presence here because they do feast on pesky insects, even though they have irritated many locals because of where they choose to poop, trespass, etc. This has resulted in various plans and schemes to deal with them over the years in what’s been called the “Great Key West Chicken Controversy” or “Key West Chicken Wars.”

I noticed that chickens will often scamper at the sight of a camera, but if you really want a good picture of them, they are more apt to stay put as you focus your camera at the post office on 400 Whitehead Street, which is just a couple of blocks west of the main drag Duvall Street.

Those sunsets, those sunsets!

sunset in Key WestA setting sun has this ability to captivate the eyes of its admirers. I’ve seen beautiful sunsets in Wyoming, but I must say that the two I saw in Key West really gripped me so unexpectedly, for I never imagined sunsets being that impacting. I first watched one from the brick walkway of Mallory Square, which overlooks the Gulf of Mexico, and the other while on a sunset cruise.

As I got closer to Mallory Square to view my first Key West sunset, the sounds of blues music and the humming of the crowd dominated as I arrived at the adjacent outdoor restaurant called Sunset Pier. Many folks were snapping pictures as the setting sun tried to make it to the horizon before being overtaken by massive clouds, even while sailboats continuously darted across the gulf. At the square were other sights and scents I took note of, including the heavenly scent of buttered popcorn mixed with the saltiness of the sea, various musical and theatrical acts (which one performer employed his dog to take tips from the onlookers’ hands and deposit it in a bucket). One outspoken guy was selling Jesus to the onlookers as if Mallory Square were the tropical version of London’s Speakers’ Corner.

The next night’s sunset was even more impressive for me, as the Sebago Key West catamaran set sail around the shores of the island city via its “Champagne Sunset Sail” tour. The sun was still in full glory, but gusty winds helped to keep me and the other passengers cooler. I observed the other cruisers. They all seemed to be from another planet, given that their faces had this “never been stressed out look” on them. Jimmy Buffet music blared from the loudspeakers as the champagne and other liquid inducements flowed.

This place does seem to be the “land of the eternal summer,” for others who live in the Northern Hemisphere were retreating to the warmth of their domiciles while I was alone with my thoughts in the open waters. Once the sun set, the skies entertained my eyes with a violet-orange haze before total darkness came except for the lights of distant ships, glowing like distant Christmas trees. Never had darkness brought so much beauty.

“Conch Architecture”

I strongly advise travelers in Key West to get off the beaten path from the touristy Duvall Street, and walk through the surrounding residential neighborhoods of Old Town. It’s here where I found a respite from the hustle and bustle of traffic while getting a glimpse into a unique kind of architecture called Conch Architecture. This style compliments the various plantlife in the area like hibiscus, fiscus, gumbo limbo, and frangipani. Earlier settlers of Key West used lime made from burned Conch shells to help build their homes, which became known as “Conch Houses”, a name which would stick even as wood became the prime building material.

These homes implement different styles, influenced by New England, Gulf Coast, Bahamian, and African influences. To my eyes, they greatly reminded me of the old plantation homes still found in the “Deep South” such as seen in such movies like Gone with the Wind. They are built to help withstand the tropical climate. I especially noticed the sloping roofs, which help reflect the sun better and sent water down to the gutters more efficiently.

One of the best-preserved neighborhoods I found is just a few blocks from the pulsating energy of Duvall Street. From the intersection of Duvall Street and Truman Ave. (US 1), walk East several blocks until you get to Windsor Ave., then turn left and begin walking north (you’ll come to a fork which gives you the option of continuing north on either Elizabeth, William, or Margaret Streets) until you get to the Key West Seaport. This walk alone will give you a good idea of what a residential tropical neighborhood is like. Many of these homes sell for a million dollars and up, but admiring from the sidewalk is still free.

As for Duvall Street itself, I noticed that even popular chain stores like Walgreens have had their structures conforming to the “Conch” aesthetics.

See a Little “White House” Without All the Fuss

Harry Truman's Little White HouseAs a U.S. presidential history buff, I was pleasantly surprised to find that I could easily visit a place where numerous Presidents of the United States stayed and performed their duties, most notably Harry S. Truman. He lived and worked at “The Little White House” for 175 days via 11 working vacations from 1946-1952. Even on “vacation” here, he still had to sign his name 200-600 times a day to help keep the country running in a place originally built for the US Navy’s base commander and paymaster in 1890. Unlike the other White House farther north, I didn’t have to make any special arrangements or go through any other fuss to walk around a property containing the 8,700 square foot house and nicely-manicured lawn and gardens. It’s in the midst of a quiet neighborhood, a short walk away from Duvall Street. I can see why our past leaders must’ve found the property to be a respite just as I did from the boisterous tourist crowds.

Besides Truman, other presidents have stayed here, so visiting means you’ve set foot on grounds that America’s most famous people have, like Dwight W. Eisenhower, who recovered from a from a heart attack here in late 1955 to early 1956. John F. Kennedy met with British Prime Minister Harold Macmillan in 1961 a few weeks before the Bay of Pigs. Jimmy Carter and Bill Clinton have also stayed here. Other people of note who’ve used this place include former Secretary of State Colin Powell to hold peace talks between Armenia and Azerbaijan in 2001 while Thomas Edison stayed here half a year in 1918 to conjure up some new weapons during World War I. The Defense Department was created here by the Joint Chiefs of Staff.


Private Key West Sunset Sail

If You Go:

♦ Sebago Key West
♦ Harry S. Truman Little White House:
♦ Florida Keys Tourism:


Small-Group Key West Food Tasting and Cultural Walking Tour

About the author:
Roy A. Barnes writes from southeastern Wyoming and is a frequent contributor to Travel thru History. The author attended a press trip sponsored by Florida Keys Tourism, but what he wrote is his own observations, and not vetted by the sponsor.

First Key West sunset photo by Yinan Chen from Pixabay
All other pictures credited to Roy A. Barnes, Carol Tedesco, and Carol Shaughnessy, and may not be used without permission.

Tagged With: Florida travel, Key West attractions Filed Under: North America Travel

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