The Most Loved Places in Key West – Now in Watercolor!

1. Captain Tony’s Saloon

Captain Tony’s Saloon is a famous bar in Key West. It has a colorful history and a lively atmosphere. Located on Greene Street, it is a popular spot for locals and tourists alike. The building itself dates back to the 1850s and has served many purposes, from an icehouse to a morgue.

Inside, the walls are covered with memorabilia, including old photos, bras, business cards, and license plates. Each item tells a story. The bar is named after Captain Tony Tarracino, a former mayor of Key West and a local legend. Captain Tony bought the bar in 1958 and made it a hub for musicians, writers, and free spirits.

Live music is a staple at Captain Tony’s. Many famous artists, including Jimmy Buffett, have performed here. The bar’s laid-back vibe and rich history make it a must-visit spot. Whether you’re enjoying a cold drink or soaking in the atmosphere, Captain Tony’s Saloon offers a unique glimpse into Key West’s past.

2. Green Parrot Bar

The Green Parrot Bar is a beloved Key West institution. Located on Whitehead Street, it’s just steps away from the Ernest Hemingway Home and Museum. The bar has a reputation for great live music and a fun, no-frills atmosphere.

The Green Parrot opened its doors in 1890, making it one of the oldest bars in Key West. Originally a grocery store, it later became a bar for Navy sailors stationed nearby. Today, it welcomes a diverse crowd of locals and tourists. The bar’s motto is “A Sunny Place for Shady People,” reflecting its laid-back and welcoming vibe.

Inside, you’ll find a jukebox, a pool table, and walls covered with quirky decorations. The Green Parrot is famous for its live music, hosting bands from all over the world. It’s a great place to enjoy a drink, listen to music, and experience the authentic Key West spirit. Whether you visit during the day or night, the Green Parrot Bar always offers a good time.

3. Hemingway House

The Ernest Hemingway Home and Museum is a must-visit in Key West. This historic house is where the famous author lived and wrote some of his most famous works. Located on Whitehead Street, it’s a beautiful property with lush gardens and a charming atmosphere.

Hemingway lived here in the 1930s, and the house is filled with his personal belongings and furniture. You can see his writing studio, where he penned novels like “For Whom the Bell Tolls” and “To Have and Have Not.” The house itself is a stunning example of Spanish Colonial architecture.

One of the unique features of the Hemingway House is its resident cats. These polydactyl cats, many of which have six toes, are descendants of Hemingway’s own pets. They roam the property freely and are a favorite among visitors.

Guided tours offer fascinating insights into Hemingway’s life and work. The knowledgeable guides share stories about his time in Key West and his love for the island. The Ernest Hemingway Home and Museum is a captivating place that offers a glimpse into the life of one of America’s greatest writers.

4. Key West Lighthouse

The Key West Lighthouse is a historic landmark that offers stunning views of the island. Located on Whitehead Street, it’s just across from the Ernest Hemingway Home and Museum. Built in 1848, the lighthouse has been guiding ships safely to shore for over a century.

Visitors can climb the 88 steps to the top of the lighthouse for a panoramic view of Key West. The climb is worth it, as the views are breathtaking. You can see the turquoise waters of the Gulf of Mexico and the historic streets of Old Town Key West.

The lighthouse also has a Keeper’s Quarters Museum. Here, you can learn about the lives of the lighthouse keepers and their families. The museum displays various artifacts, including old photographs and tools used by the keepers.

The Key West Lighthouse is a piece of maritime history and a must-see attraction. It’s a great spot for photos and offers a unique perspective of the island. Whether you’re interested in history or just want to enjoy the view, the lighthouse is a highlight of any visit to Key West.

5. Sloppy Joe’s Bar

Sloppy Joe’s Bar is an iconic Key West establishment with a rich history. Located on Duval Street, it has been a favorite spot for both locals and tourists since it opened in 1933. The bar is famous for its lively atmosphere, great drinks, and live entertainment.

Sloppy Joe’s was a favorite hangout of Ernest Hemingway, who was friends with the original owner, Joe Russell. The bar’s name and its connection to Hemingway add to its allure. Inside, the walls are adorned with photos and memorabilia, creating a nostalgic and welcoming environment.

Live music is a big part of Sloppy Joe’s appeal. The bar hosts bands and solo performers every night, offering a mix of rock, country, and blues. It’s a great place to dance, sing along, and enjoy the vibrant nightlife of Key West.

The bar’s menu features a variety of drinks and pub fare, including the famous Sloppy Joe sandwich. Whether you’re stopping in for a quick drink or spending the evening, Sloppy Joe’s Bar promises a good time. It’s a must-visit spot that captures the fun and carefree spirit of Key West.

6. Southernmost Point

The Southernmost Point is one of Key West’s most famous landmarks. Located at the corner of South Street and Whitehead Street, it marks the southernmost point of the continental United States. The spot is marked by a large, colorful buoy that has become an iconic photo op for visitors.

The buoy is painted in bright red, yellow, and black, with the words “Southernmost Point Continental U.S.A.” and “90 Miles to Cuba” written on it. This spot offers a unique chance to stand at the edge of the country and look out over the ocean toward Cuba.

The area around the Southernmost Point is always bustling with tourists taking pictures and enjoying the view. There’s often a line, but the wait is worth it for a memorable photo. The nearby shops and cafes add to the lively atmosphere, making it a fun place to explore.

Visiting the Southernmost Point is a quintessential Key West experience. It’s a simple yet significant landmark that symbolizes the island’s unique position. Don’t miss the chance to snap a photo and take in the ocean views at this iconic spot.

7. Sunset at Mallory Square

Sunset at Mallory Square is a daily celebration that captures the magic of Key West. Located on the waterfront in Old Town, Mallory Square is the perfect place to watch the sun dip below the horizon. Every evening, locals and tourists gather here to enjoy the stunning sunset and festive atmosphere.

The Sunset Celebration at Mallory Square features street performers, musicians, and local artists. You can watch acrobats, jugglers, and magicians while browsing stalls selling handmade crafts and souvenirs. The lively entertainment adds to the charm and makes the experience memorable.

As the sun sets, the sky transforms into a canvas of vibrant colors, reflecting off the water. The view is breathtaking and offers a perfect photo opportunity. Many people come early to find a good spot and enjoy the pre-sunset activities.

Mallory Square is also home to several waterfront bars and restaurants. You can grab a drink or a bite to eat while watching the sunset. The combination of beautiful views, lively entertainment, and great food makes sunset at Mallory Square a highlight of any Key West visit.

8. The Southernmost House

The Southernmost House is a historic and luxurious hotel located at the southern tip of Key West. This stunning Victorian mansion dates back to the late 1800s and offers a blend of history, elegance, and modern amenities. It’s situated on Duval Street, just steps away from the Southernmost Point.

The mansion features beautiful architecture, with intricate woodwork, stained glass windows, and a wraparound veranda. The property includes lush gardens, a large pool, and direct access to the ocean. Guests can enjoy the tranquil atmosphere and stunning views from the comfort of this historic home.

The Southernmost House has hosted many famous guests, including presidents and celebrities. Today, it offers 18 luxurious rooms and suites, each uniquely decorated with antique furnishings and modern conveniences. The hotel also features a poolside bar, where you can enjoy a refreshing drink while soaking in the sun.

Staying at the Southernmost House offers a unique experience that combines the charm of old Key West with the comforts of a modern luxury hotel. Whether you’re relaxing by the pool, exploring nearby attractions, or simply enjoying the beautiful surroundings, the Southernmost House provides an unforgettable stay.

9. Historic Seaport

The Historic Seaport is a vibrant and bustling area in Key West. Located along the waterfront, it’s a hub of activity with a rich maritime history. The seaport is home to a marina, shops, restaurants, and a variety of water-based activities.

Walking along the boardwalk, you’ll see historic schooners, fishing boats, and luxury yachts. The seaport offers a glimpse into Key West’s seafaring past and present. You can take a sunset cruise, go fishing, or rent a kayak to explore the waters.

The area is also known for its excellent seafood restaurants. Fresh catches from the local waters are served up daily, making it a great place to enjoy a meal with a view. Many of the restaurants offer outdoor seating, so you can dine while watching the boats come and go.

In addition to dining and water activities, the Historic Seaport hosts events and festivals throughout the year. The lively atmosphere and beautiful waterfront setting make it a favorite spot for both locals and visitors. Whether you’re looking to relax, dine, or embark on an adventure, the Historic Seaport has something for everyone.

10. Mile 0

Mile 0 in Key West is a famous spot. It marks the start of U.S. Highway 1, which stretches all the way to Maine. This spot is a popular place for tourists to take photos. The sign is small but iconic, showing the beginning of a long and historic road.

Many visitors feel a sense of accomplishment when they reach Mile 0. It symbolizes the end of a journey or the start of a new one. The surrounding area is filled with shops, restaurants, and attractions, making it a lively spot.

Mile 0 is not just a marker; it’s a piece of American road history. People from all over the world come to see it. Whether you drive the whole highway or just visit Key West, this marker is a must-see. It’s a simple but powerful symbol of travel and adventure.

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