Discover Key West: A Tropical Paradise Steeped in History and Adventure

Discover Key West: A Tropical Paradise Steeped in History and Adventure

Imagine a place where the vibrant colors of the Caribbean meet the charm of historic architecture, where roosters roam freely and sunsets paint the sky with breathtaking hues – welcome to Key West, the ultimate destination for history lovers, adventure seekers, party animals and those craving a slice of tropical paradise.Extending 150 miles southwest from mainland Miami, the Florida Keys comprise one of America’s most epic vacation destinations. Travelers seeking a laid back atmosphere and natural beauty are sure to find it in this subtropical paradise, where each key has its own unique personality and draw. From the fabled island of Key West to the magnificent coral reefs of Islamorada.

Creating New Memories in Key West: A Journey with Day

After visiting Key West several times and stay in the Hyatt , and  the Opal Key Resort & Marina & the Sunset Key cottage this trip is special—it’s my first time here with Day. I am eager to share with her the experiences that have given me so many beautiful memories. This charming little city, with its unique atmosphere, vibrant culture, and stunning nature, the breathtaking sunset and  and street performers,Has always held a special place in my heart. I know Day will love the distinctive style of the houses and nature here, something she greatly appreciates.

You can reach Key West either by plane, boot or car. We chose to drive from Miami with a rental car, over the Overseas Highway, also known as U.S. Route 1, offers breathtaking views of the Atlantic Ocean and the Gulf of Mexico. Each stop along the way, from Key Largo, Islamorada to Marathon ( turtle hospital )and finally to Key West, presents unique attractions and opportunities to explore the beautiful surroundings. This is highly recommended because the route is absolutely stunning, taking you over numerous islands and bridges.

If You fly directly into the Key West International Airport and take a Lyft to your accommodation. you just have to love this one. It’s just one room, with two luggage claims, and one security guard who just looks at you and nods. Yup, this airport is just as relaxed as the rest of the island. And if you want to get started with relaxation the instant you get on the island, there is a tiki bar. That’s the layout: tiki bar, security guard, two luggage claims, and a bathroom. It’s amazing.

This time, instead of staying in the bustling downtown area where the nightlife hums until the early hours, we opted for a quieter stay at the Havana Cabana. This hotel, just a little bit outside the city center, offers a perfect blend of relaxation and fun with its Cuban 60s vibe and fantastic swimming pool. It feels like a slice of the Caribbean, despite being so close to all the action.

Exploring the Heart of Key West

During our stay in Key West, we chose to reside at the delightful Havana Cabana, a charming hotel just outside the bustling downtown area.

This location proved perfect for us as it offered a peaceful retreat away from the lively nightlife that can carry on late into the night in the city center. Havana Cabana boasts a splendidly large swimming pool, creating a serene Caribbean island ambiance despite being close to the city.

From Havana Cabana, we had convenient shuttle service to downtown, making it easy to dive into the heart of Key West. Alternatively Renting bikes or scooters was also an option, giving us the freedom to explore at our own pace. One of our first stops was the iconic Southernmost Point buoy, where we snapped photos and soaked in the significance of being at the edge of the continental United States.

The highlight of any Key West visit is undoubtedly the sunset at Mallory Square. We joined the crowd to watch the sun dip below the horizon, casting golden hues over the water while street performers entertained and vendors sold unique crafts and snacks. This vibrant scene encapsulated the lively spirit of Key West, and it was a joy to share it with my girl Day.

Discovering Hidden Gems

Our adventure didn’t stop there. We wandered through the
quaint streets, exploring boutique shops and enjoying ice cream on the cozy terraces. Each corner of Key West offers something special, from the historic Shell house to charming little breakfast spots where we indulged in delicious morning meals.

For anyone planning a trip to Key West, I highly recommend considering a stay at the Havana Cabana. Its relaxing ambiance and fantastic amenities provide a perfect retreat after a day of exploration. Whether you’re here for the first time or returning for another visit, Key West promises new experiences and cherished memories every time.

 

 

So let me take you to Discover Key West: History, Attractions, and Insider Tips

Key West, a paradise island at the end of the Florida Keys, offers a rich history, unique culture, and plenty of adventures. Colourful coral reefs, as well as being considered a safe place for LGBTQ+ people. While you won’t find Mickey Mouse here, there are plenty of drag shows, a living doll, and a lot of six-toed cats. A haunted doll. Key West, Florida may be one of the most unique places in America: roosters roam the streets, drag queens rule the nightlife, and Cuba’s close proximity colors its history. The entire island is a colorful, tropical feast for the senses. 

To really appreciate Key West in all of its quirky glory, you also have to get to know its long history of pirates, bootleggers, and nonconformists; its resident ghosts and grave-digging iguanas; and the resident animals who call it home.

Key West has something for everyone. In this comprehensive guide, we’ll explore the history, charm, and activities that make Key West a must-visit destination.

Of course, no visit to Key West is complete without a trip to the southernmost point of the continental United States, where we captured memorable photos. We also made sure to witness the breathtaking sunset at Mallory Square, where local artists perform and charming stalls offer unique souvenirs. Our exploration also led us to visit the iconic Shell House and discover quaint, cozy breakfast spots scattered throughout the area

CHECK OUT KEY WEST’S HISTORICAL HOMES

Key West’s history has shaped it into the quirky destination it is today, and is reflected in its many historical homes and local legends. Understanding Key West’s history makes wandering its colorful streets all the more enjoyable!

Before the island’s name was anglicized, to Key West, it was called Cayo Hueso, or Bone Island, by the Spanish who charted the island in 1513 when they were off looking for the Fountain of Youth.

Before the arrival of the Spanish, the Florida Keys, including Key West, were inhabited by the Calusa and Tequesta peoples, who were known as skilled fishermen and expert sailors. Sadly, both the Calusa and Tequesta people were decimated by the late 1700s due to European diseases and conflicts.

Key West, also known as the Conch Republic, has a fascinating history dating back to the early 1800s. Originally inhabited by the indigenous Calusa people, the island was later claimed by Spain before being sold to the United States in 1821. Throughout the 19th century, Key West blossomed into a thriving port town, known for its salvaging operations, cigar manufacturing, and strategic naval presence.

By the mid-1800s, Key West was the richest city per capita in the United States, thanks to its lucrative wrecking industry, where locals salvaged valuable goods from shipwrecks off the coast. This era left a lasting impact on the island, shaping its architecture and culture. Today, visitors can explore historic sites like the Key West Shipwreck Museum to learn more about this intriguing period.

MEET KEY WEST’S RESIDENT ANIMALS

       

Key West has no shortage of tropical birds, lizards, and bugs on the island – not to mention the roosters and cats, which aren’t tropical at all, but are very much a part of Key West life.

iguanas. The green iguanas are an invasive species believed to be stowaways on ships from Central and South America, and they’re considered quite a local nuisance (apparently, they like to dig up graves). That said, leave eradication to the professionals. Iguanas are amazing, beautiful animals and you might think it’s ok to pick them up for a picture – but it is not ok. It stresses the animal, and they could seriously hurt you with their claws! For your own safety, don’t touch them.

• Key West is home to a lot of six-toed cats. I blame Ernest Hemingway, who lived there and had a 6-toed cat, and now his historic house is home to 60 of them! While most of these cats are friendly, please don’t try to pet them. They are still wild animals and as a general rule of thumb, don’t try to pet wild animals.

So why Do Chickens Roam Freely in Key West?

One of the most charming and quirky aspects of Key West is its free-roaming chickens. You are going to hear and see more chickens than you ever have before in your life here.These birds are descendants of domestic chickens brought to the island by early settlers and Cuban immigrants. Cockfighting was popular in Key West in the 1800s and 1900s, until it was banned. When that happened, all the chickens were suddenly released to the island. No one made an effort to get rid of them,Over time, they adapted to the wild, now they are welcome on the island as friendly wildlife and becoming an integral part of Key West’s unique character.

In Key West, these chickens are more than just a quaint sight—they’re protected by law. This protection stems from their historical significance and the role they’ve played in the island’s culture. Locals affectionately refer to them as “gypsy chickens,” and they can be seen strutting around streets, parks, and even outdoor cafes. Their presence adds to the laid-back, free-spirited vibe that Key West is famous for.

• Key West Butterfly Conservatory

The conservatory feels like paradise, filled with colorful butterflies and birds, tropical flowers and waterfalls. There are about 50 species of butterflies here. Perch on a butterfly-shaped bench and sit and watch them snacking on fruit – if you’re lucky, one might even land on you to say hello.

You’ll also see also flamingoes, turacos, lizards, and other brightly colored birds that I don’t know the names of (just know they’re all tropical and very friendly). On your way out, pick up a glass-sculpted butterfly hand-crafted by the conservatory’s owner in the gift shop as a souvenir!

The Oldest House in Key West

The Oldest House Museum, located at 322 Duval Street, dates back to 1829 and stands as a prime example of early Key West architecture. Built by Captain Francis Watlington, this historic home offers a glimpse into the past with its original furnishings, family heirlooms, and beautifully maintained gardens.

Visitors to the Oldest House can explore exhibits detailing the lives of the Watlington family and the broader history of Key West. The museum also hosts events and provides educational programs, making it a must-visit for anyone interested in the island’s rich heritage.

Architectural Style and Boutique Shops

Key West is renowned for its distinctive architectural style, characterized by conch houses with pastel colors, wrap-around porches, and lush gardens. These charming homes reflect the island’s Caribbean influences and maritime history. Walking through the streets of Key West, particularly in the Old Town area, feels like stepping back in time.

In addition to its beautiful homes, Key West boasts a vibrant shopping scene with numerous boutique shops. Duval Street, the main thoroughfare, is lined with unique stores offering everything from local art and crafts to fashionable clothing and souvenirs. Highlights include the Key West Island Books, a beloved independent bookstore, and the Key West Art Center, showcasing works by local artists.

Best Restaurants in Key West

Key West’s culinary scene is as diverse as its history, with an array of restaurants catering to all tastes. Here are some top picks that should not be missed:

– **Blue Heaven**: This iconic spot is perfect for breakfast, offering delicious dishes in a tropical, laid-back setting complete with roaming chickens. Signature items include the Lobster Benedict and the famous Key Lime Pie.

– **Latitudes**: Located on Sunset Key, this upscale restaurant offers breathtaking views and exquisite seafood. Accessible by ferry, Latitudes provides a romantic dining experience with dishes like Key West pink shrimp and yellowtail snapper.

– **Santiago’s Bodega**: A favorite for tapas lovers, Santiago’s Bodega features a cozy atmosphere and a diverse menu with highlights such as beef tenderloin skewers and bacon-wrapped dates.

– **The Breakfast Club, Too**: Ideal for breakfast and brunch, known for its creative dishes and friendly service. Must-tries include the stuffed French toast and avocado toast.

  

Activities and Must-See Attractions

There’s no shortage of activities to enjoy in Key West. Here are some top recommendations:

– **Jet Ski Tours**: Explore the island from the water with an exhilarating jet ski tour. These guided excursions offer a fun way to see Key West’s coastline and nearby islands.

– **Sunset Cruises**: Experience the famous Key West sunset from a boat, complete with drinks and live music. Popular options include the Schooner Jolly II Rover and Fury Water Adventures.

– **Seaplane Tours**: Get a bird’s eye view of the beautiful islands and marine life surrounding Key West. Seaplane tours to the Dry Tortugas are especially popular, offering stunning aerial views and a chance to explore Fort Jefferson.

– **Day Trips**: Visit nearby Dry Tortugas National Park, known for its pristine beaches, crystal-clear waters, and historic Fort Jefferson. Accessible by boat or seaplane, this remote destination is a favorite among snorkelers and history enthusiasts.

Must-See Sights

No trip to Key West would be complete without visiting these iconic attractions:

Hemingway House & Museum is in Old Town Key West, and this yellow, airy, many-windowed home is in the French Colonial style with many art deco accents on the inside. complete with lush gardens and the descendants of Hemingway’s six-toed cats. The guided tours provide fascinating insights into Hemingway’s life and work.This is a really big attraction on Key West for good reason – Hemingway was a prolific writer during the 1920s and 30s, and he wrote two of his most famous books in this very house: A Farewell To Arms and To Have and Have Not.

Ernest Hemingway lived in Key West for years, making the island his permanent place of residence in the 1930s.

– **Southernmost Point Buoy**: Snap a photo at this iconic landmark, marking the southernmost point in the continental United States. It’s a popular spot for tourists, so arrive early to avoid the crowds.

– **Mallory Square**: Join the daily Sunset Celebration at Mallory Square, where street performers, local artists, and food vendors create a festive atmosphere. It’s the perfect place to end your day with a beautiful sunset over the Gulf of Mexico.

The Famous Conch Train Tours

One of the best ways to explore the charming streets and historic sites of Key West is by hopping aboard the Conch Train. Since 1958, this beloved tourist attraction has been delighting visitors with its fun and informative tours, offering a unique perspective on the island’s rich history and vibrant culture.

The Conch Train Tour takes you on a journey through Old Town Key West, winding through picturesque streets lined with conch-style houses, tropical gardens, and historic landmarks. The tour covers over 100 points of interest, including Mallory Square, the Ernest Hemingway Home and Museum, and the Southernmost Point Buoy.

Knowledgeable and entertaining guides narrate the tour, sharing fascinating stories and anecdotes about Key West’s past and present. You’ll learn about the island’s early settlers, its role in the shipwreck salvage industry, and the vibrant cultural influences that have shaped its unique character.

The train makes several stops along the way, allowing passengers to hop off and explore attractions up close before reboarding to continue their adventure. It’s a convenient and enjoyable way to see the sights, especially for those looking to make the most of their visit without the hassle of navigating on their own.

In addition to the classic Conch Train Tour, there are also special themed tours available, such as the Christmas Lights Tour during the holiday season, which showcases the beautifully decorated homes and streets of Key West.

The Conch Train is more than just a mode of transportation—it’s an iconic Key West experience that provides a delightful and engaging way to discover all that this enchanting island has to offer. Whether you’re a first-time visitor or a seasoned traveler, the Conch Train Tour is a must-do activity that promises to leave you with lasting memories of your time in Key West.

Duval Street: Key West’s Vibrant Shopping and Dining Hub

Duval Street is the bustling heart of Key West, renowned for its eclectic mix of shops, galleries, restaurants, and vibrant nightlife. Stretching from the Gulf of Mexico to the Atlantic Ocean, this iconic street offers something for everyone, whether you’re looking to shop, dine, or simply soak in the island’s unique atmosphere.

Shopping Experience

Duval Street is a shopper’s paradise with an array of boutiques, art galleries, and souvenir shops. You can find everything from local artwork and handmade crafts to fashionable clothing and jewelry. Explore Key West Island Books for a literary escape, or visit the Key West Art Center to admire works by local artists. Whether you’re searching for a unique gift or a piece of island-inspired decor, Duval Street has it all.

Dining and Nightlife

Beyond shopping, Duval Street is also famous for its dining scene and vibrant nightlife. From casual eateries to upscale restaurants, there’s a culinary delight to suit every taste. Enjoy fresh seafood at Half Shell Raw Bar, savor Cuban cuisine at El Meson de Pepe, or indulge in a slice of Key Lime Pie at Kermit’s Key West Key Lime Shoppe.

As night falls, Duval Street comes alive with bars and clubs offering live music, craft cocktails, and a lively atmosphere. Experience the laid-back vibe of Irish Kevin’s, dance the night away at Sloppy Joe’s Bar, or enjoy a sunset toast at the iconic Sunset Pier.

Alongside its modern attractions, Duval Street is home to several historic landmarks that offer glimpses into Key West’s past. Visit the Audubon House and Tropical Gardens to explore a restored 19th-century home or step into the Custom House Museum to learn about the island’s maritime history. Don’t miss the iconic Southernmost Point Buoy, marking the southernmost tip of the continental United States and a popular photo spot for visitors.

Duval Street is more than just a shopping destination—it’s the vibrant pulse of Key West, where history meets modernity, and every corner tells a story. Whether you spend an afternoon browsing boutiques, savoring local cuisine, or dancing under the stars, Duval Street promises an unforgettable experience in paradise.

Explore the charm and excitement of Duval Street, where shopping, dining, and entertainment come together to create the quintessential Key West experience.

 Celebrations: Carnivals and Parades in Key West

Key West is not only known for its stunning landscapes and rich history but also for its lively festivals and parades that bring the island to life with color, music, and revelry. One of the most famous events is Fantasy Fest, held every October. This ten-day extravaganza is Key West’s version of Mardi Gras, featuring elaborate costumes, street parties, and grand parades. Each year, Fantasy Fest has a different theme, inspiring participants to showcase their creativity with dazzling outfits and floats.

OFF TO THE (DRAG) RACES

Throughout the year, Duval Street hosts various events and festivals that showcase Key West’s culture and community spirit. From the lively Fantasy Fest celebrations in October to the festive Holiday Fest activities in December, there’s always something exciting happening on Duval Street. Be sure to check local calendars for events like the Duval Street Crawl or the Key West Songwriters Festival for unforgettable experiences.

Being so secluded from the mainland, Key West was largely unheard of until the 1970s, when it became a LGBTQ+ destination due to large influxes of LGBTQ+ members moving in and renovating the older homes on the island.

So another highlight is the Key West Pride Festival, celebrated every June. This vibrant event honors the LGBTQ+ community with a week of parties, parades, and cultural activities. The Pride Parade down Duval Street is a joyful explosion of color and inclusivity, attracting visitors from around the globe.

For a more traditional celebration, the Conch Republic Independence Celebration in April commemorates Key West’s tongue-in-cheek secession from the United States in 1982. The festivities include a whimsical bed race, a “drag” race featuring local drag queens, and a grand parade, all celebrating the island’s quirky spirit and independence.

During the holiday season, the Holiday Fest transforms Key West into a festive wonderland. Highlights include the Lighted Boat Parade, where decorated vessels of all sizes parade through the harbor, and the Historic Seaport’s Bight Before Christmas, featuring a tree lighting ceremony, holiday music, and seasonal treats.

These carnivals and parades encapsulate the lively, inclusive, and celebratory spirit of Key West. They offer visitors a chance to immerse themselves in the local culture and join in the island’s most beloved traditions.

GO SNORKELLING IN A CORAL REEF

One of the most fun ways to enjoy the local environment is snorkelling! Day and i are OBSESSED with snorkelling. Coral reefs are a whole new world to explore: underneath the blue water there is an abundance of fish and neon-colored coral to see. With all the life here, you can stay in the water for hours and still find yourself noticing new details, with sea critters swimming every which way.

But before you go snorkelling, a few crucial notes: always use the buddy system, don’t touch the coral -for your safety as well as its and make sure you’re wearing reef-safe sunscreen, NOT regular sunscreen.

If you’re not confident about your snorkeling skills or you’ve never gone before, we included a few guided tour options.

WHAT WILDLIFE CAN I SEE WHILE SNORKELING?

Key West has a lot of big, beautiful fish! Some of the ones to keep an eye out for while snorkeling are:

• • • Parrotfish: Key West has an abundance of Parrotfish! Rainbow Parrotfish are especially eye-catching. If you go snorkeling and see these fish near coral, stop swimming for a second and listen – Parrotfish keep coral clean by using their teeth to scrape them, and you can actually hear this in the water.
    • Manatees: Manatees are super cool to see in the water! You are more likely to see them in areas with seagrass rather than a coral reef, since they graze on seagrass. If you see a manatee, consider yourself lucky because you just saw a mermaid. It’s thought that sailors started the legend of mermaids by mistaking manatees for humans with tails from afar.
    • Dolphins: The Keys are filled with bottlenose dolphins, so the likelihood of you seeing a few jumping and playing in the water is pretty high. Dolphins in Florida oftentimes give birth in spring and summer, so if you visit during these times try to keep an eye out for any small calves swimming right under their mothers. Certain tours, like this one, will take you to specific spots where bottlenose dolphins tend to hang out!
    • Stingrays: To see stingrays in Key West, you’ll have to really keep an eye out. Stingrays tend to lay in the sand and rest so you might swim right over one without even noticing it! The easiest way to spot a stingray in sand is by looking for a sandy rock that appears to have eyes, and sometimes a tail if the particular stingray is feeling too lazy to bury itself in all the way. However, if a Giant Manta Ray passes by you, you definitely won’t be able to miss it. When these rays are born, they’re already six feet wide, and an adult can soar through the water with lengths of 24 feet.
    • Sea Turtles: If you’re really lucky, you might see a sea turtle! Several species live in the Keys. The most common ones are Loggerheads and Green sea turtles. Sea turtles are most often found floating along in the currents, looking more relaxed than any beach-goer.
    • Sharks: Most sharks here aren’t particularly dangerous species- nurse, lemon, and sandbar sharks are the most common. I actually saw a sandbar shark one time while snorkeling! There has never been a fatal shark attack in the Keys- just don’t be the first by trying to pet one, as cute as they are.

WHERE CAN I GO SNORKELING IN KEY WEST?

Key West is surrounded by reefs, but they’re a little ways offshore – the easiest way to get to them is by boat. That said, there are a few great places around the island to snorkel and see some of these ocean creatures in their native habitats:

• Fort Zachary Taylor State Park: The only reef I know of that you can reasonably swim to is the one in Fort Zachary Taylor. The admission for pedestrians is $2.50 and you can spend the entire day there- there’s not only swimming, but the park is known for having many tropical species of birds you can see. These reefs may be your best chance to catch a glimpse at the elusive sea turtle as well! Since you will be on your own in this reef, make sure you bring your own snorkeling gear or rent one at the park (either way, pack anti-fog spray).
• Dry Tortugas National Park: Thanks to efforts by the local government to keep the island reefs alive, this reef is healthy and happy – so if you want to see one that is really thriving this is the place to go. It’s colorful, with a variety of coral species and plenty of fish to see! Dry Tortugas is also home to historic Fort Jefferson. Note that in order to get to Dry Tortugas you have to take a boat and purchase an entrance fee to the National Park.
• Book a Snorkeling Tour: The good thing about snorkel tours is that they will provide snorkeling gear and help from the guides, along with the guide’s knowledge on the area and local animals. This snorkel tour takes you out to the Great Florida Reef –  the only living coral barrier reef in the United States and the third-largest in the world – on a 69-foot catamaran for 3 hours of fun in the water. Or, take a gamble on the Island Adventure Eco Tour: each tour is different and the snorkeling location varies depending on the weather and what animals are swimming around where! You can also choose to end your afternoon with kayaking at sunset – what a perfect Key West day!

ENJOY THE SUNSETS

The sunsets in Key West are amazing. I’m not sure what it is- maybe it’s the way the sun reflects off the water – but the sunsets aren’t one to miss.  The skies turn pink and orange in the evening, and the sky slowly fades from those bright colors to a blue night with tons of stars. There isn’t a lot of light pollution in the Keys, so the stars shine brighter than they would in cities.

It really does look like something out of a painting and cameras just don’t do it justice! Here are a few ways to enjoy Key West’s incredible sunsets:

• Sunset Cruises

Sunset cruises are really popular, and I’ve gone on one every single time I’ve been to Key West. The sunset cruises normally give out free beverages – because Key West is always down to party – and are the absolute best way to see the sunset.

Most of these tours are about two hours long, returning at around 7pm. Note that since these are sailboats, the downstairs space of the boat is pretty much just a bathroom and not a space to hide from the sun, so if you burn as badly as I do make sure you bring sunblock!

If you’re traveling with your partner, book an intimate cruise like Danger’s Charters Wind & Wine Sunset Sail Sitting on a boat and watching the sunset together is such a romantic way to spend time with each other!

For a livelier evening, Cool Key West is a great choice, with local musicians playing and plenty of free drinks.

Sunset Catamaran Cruise in Key West

Experience the magic of a Key West sunset aboard a catamaran. Sail into the horizon as the sky transforms with vibrant hues of orange, pink, and purple. Enjoy the gentle sea breeze, live music, and refreshing drinks while witnessing one of nature’s most beautiful spectacles. This unforgettable evening on the water is a must-do when visiting Key West.

• Sunset Celebration at Mallory Square

Every evening in Mallory Square, the Sunset Celebration happens! This is a really cool part about Key West- every night, performers and street artists set up booths to sell their goods and perform. You can take in the ocean breeze while celebrating the beauty of the sunset and watching people swallow swords or juggle fire.

Or If you  get your tarot cards read at a psychic booth and buy conch fritters, delicious bits of fried conch, wrapped in a thick layer of breading, garlic, and pepper.

The sunset celebration is a great way to end every day, in Key West and is the perfect way to celebrate the last evening of your visit to paradise.

When is the best time to visit Key West?

The best time to visit Key West is in the spring, between March and May. By this time of year, it will be about 80-85 degrees during the day and before hurricane season begins, so you won’t have to worry as much about random showers interrupting your day. The peak winter tourist season will also have ended, so the island will be less crowded and places to stay will typically be cheaper.

Sloppy Joe’s Bar: A Legendary Key West Icon

When it comes to iconic landmarks in Key West, Sloppy Joe’s Bar stands out as a must-visit destination for both locals and tourists alike. Located on Duval Street in the heart of Old Town, this historic watering hole has been a cornerstone of the island’s nightlife and social scene since it first opened its doors in 1933.

Sloppy Joe’s Bar has a storied history that dates back to the days of Prohibition. Originally named “The Blind Pig,” it operated as a speakeasy where patrons could enjoy drinks discreetly during the era of alcohol prohibition in the United States. In 1933, when Prohibition was repealed, the bar’s founder, Joe Russell, officially renamed it “Sloppy Joe’s” and moved it to its current location on Duval Street.

Since then, Sloppy Joe’s has become synonymous with Key West’s vibrant culture and laid-back atmosphere. It has hosted countless celebrities, writers, and musicians over the years, including its most famous patron, Ernest Hemingway. Hemingway was a regular at the bar during his time in Key West in the 1930s, and his presence has left an indelible mark on its legacy.

Walking into Sloppy Joe’s is like stepping back in time to an era of casual elegance and lively camaraderie. The bar is adorned with vintage memorabilia, photographs, and fishing artifacts that pay homage to Key West’s maritime heritage. The walls are lined with signed dollar bills from patrons past and present, adding to the bar’s eclectic charm.

The atmosphere at Sloppy Joe’s is always buzzing, whether you visit during the day for a relaxed afternoon drink or join the crowds at night for live music and dancing. The bar hosts talented musicians who play everything from classic rock to local favorites, creating a soundtrack that enhances the lively ambiance.

No visit to Sloppy Joe’s is complete without trying one of their signature drinks, such as the Sloppy Rita or the Papa Doble, a cocktail famously enjoyed by Hemingway himself. The bar also serves up hearty pub fare, including their renowned Sloppy Joe sandwich—a delicious combination of ground beef, onions, and tomato sauce served on a toasted bun.

Sloppy Joe’s is not just a bar; it’s a hub of community spirit and tradition in Key West. The bar hosts various events throughout the year, including birthday celebrations for Ernest Hemingway, whose legacy is commemorated with the annual Hemingway Look-Alike Contest. This quirky event draws participants from around the world who compete to resemble the famous author and vie for the title of “Papa.”

Whether you’re a history buff, a Hemingway fan, or simply looking to soak in the lively spirit of Key West, Sloppy Joe’s Bar offers an unforgettable experience. It’s a place where stories are shared, friendships are forged, and memories are made—a true embodiment of the island’s enduring charm and allure.

Where to Stay in Key West: Luxury, Casual, and Traditional Favorites

When it comes to accommodation, Key West offers a range of options, from luxury resorts to charming inns. This time we went to**Hotel Cabana**, renowned for its largest pool on the island and superb service. This stylish hotel combines modern amenities with a relaxed island vibe, making it an ideal base for exploring Key West.

So if you love immense luxury, prefer a more casual vibe, or seek the charm of a traditional hotel in one of Key West’s historic homes, there’s something for everyone. From upscale resorts to cozy inns and even campgrounds, Key West offers a wide range of accommodations to suit every preference. Here are some of my favorietes.

Private Islands and Exclusive Experiences

For a truly exclusive experience, consider staying on one of the private islands owned by luxury resorts like the Hilton. These islands offer secluded beaches, private villas, and personalized services, ensuring a memorable and luxurious stay.

Staying at these private island resorts provides access to a range of exclusive amenities, such as private pools, gourmet dining, and customized excursions. It’s the perfect way to experience the best of Key West in style and comfort.

Whether you seek luxury, a casual stay, or the unique charm of a traditional Key West home, these options will ensure you have an unforgettable experience in this island paradise. Book your stay today and start creating your own Key West memories!

Discover the best places to stay in Key West and plan your perfect getaway!.

**Traditional Hotels:**

1. **The Southernmost House** – A historic gem with charming architecture and a prime location on Duval Street.
2. **Simonton Court Historic Inn & Cottages** – Offers a taste of old Key West with beautifully restored cottages and lush gardens.

**Camping:**

1. **Boyd’s Key West Campground** – Provides a unique outdoor experience with waterfront campsites and convenient amenities.
2. **El Mar RV Resort** – A cozy spot for RV travelers seeking a peaceful retreat near the water.

Best Value Hotel in the Florida Keys:
**The Perry Hotel & Marina**
Experience waterfront luxury at an affordable price. The Perry Hotel & Marina offers stylish rooms, excellent dining options, and easy access to water activities.

Best Hotel for Families in the Florida Keys:
**Hawks Cay Resort**
Perfect for families, Hawks Cay Resort features multiple pools, a kids’ club, and a variety of water sports. The resort provides everything needed for a fun and relaxing family vacation.

1. **Havana Cabana at Key West** – Embraces a Cuban 60s ambiance with a fantastic pool, perfect for a relaxed stay.
2. **The Gates Hotel Key West** – Combines modern comfort with a laid-back atmosphere, featuring a rum bar and food truck

**Luxury Hotels:**

Best Hotel for Couples in the Florida Keys:
**Little Palm Island Resort & Spa**
For a romantic getaway, Little Palm Island Resort & Spa is unparalleled. Accessible only by boat or seaplane, this private island resort offers secluded bungalows, fine dining, and luxurious spa services.

Best Beachfront Hotel in the Florida Keys:
**Casa Marina Key West, Curio Collection by Hilton**
This historic beachfront hotel offers elegant rooms, direct beach access, and top-notch amenities. Casa Marina Key West combines historic charm with modern luxury.

Best Boutique Hotel in the Florida Keys:
**The Marquesa Hotel**
With its intimate setting and personalized service, The Marquesa Hotel stands out as the best boutique hotel. The beautifully restored buildings and lush gardens create a serene and luxurious atmosphere.

Best Spa and Wellness Hotel in the Florida Keys:
**Ocean Key Resort & Spa**
For ultimate relaxation, Ocean Key Resort & Spa offers a full-service spa, stunning ocean views, and a tranquil setting. It’s the perfect place to unwind and rejuvenate.

– **The Marker Key West Harbor Resort**: A waterfront property with luxurious rooms, three pools, and an on-site restaurant.

– **H2O Suites**: An adults-only hotel featuring spacious suites, a rooftop pool, and personalized service

Whether you seek luxury, a casual stay, or the unique charm of a traditional Key West home, these options will ensure you have an unforgettable experience in this island paradise. Book your stay today and start creating your own Key West memories!

Discover the best places to stay in Key West and plan your perfect getaway!

 Affiliate Recommendations

When planning your trip to Key West, consider booking through these recommended services to get the best deals and experiences:

– **Hotels.com**: Find great deals on hotels, including top picks like Hotel Cabana. [Book your stay now

– **Viator**: Book exciting tours and activities like jet ski tours and sunset cruises. [Explore tours and activities

– **Booking.com**: Secure your stay at exclusive resorts with private island experiences. [Discover luxury accommodations..

Key West is a magical destination that promises unforgettable memories. From its rich history to its vibrant present, there’s something enchanting around every corner. Start planning your trip today and immerse yourself in the charm of Key West!

With love Nicole

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