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Welcome to Old Town Key West, where the past comes to life! With its historic architecture, colorful streets, and fascinating museums, this neighborhood is a must-see for anyone visiting the island.

Exploring Old Town, Key West

 

A walk through Old Town, Key West, creates a nostalgia, unlike any other famous historic area I have visited. I love the town trolley tours, but walking allows me to absorb the feel as so many famous people have done. Looking for the perfect mix of fun, history, and spirit? Look no further than Duval Street in Key West! This iconic street is a downtown commercial artery that runs from one ocean to another: filled with unique bars, quirky shops, outdoor cafés, and more. Not only are there tons of places to explore during the day – but Duval Street is also renowned for its famous “Duval Crawl” nightlife scene. Hop on your journey down memory lane today—you won’t be disappointed!

 

florida, vacations, coast

Walking Through History: Uncovering the Rich Heritage of Old Town Key West

 

 

As I take my first steps into Old Town Key West, I am immediately struck by the charm and character of this historic neighborhood. The streets are lined with colorful, wooden houses, each with their own unique style and story to tell. It’s clear that there is a rich heritage here. I can’t wait to delve deeper and uncover all that Old Town Key West has to offer. The area feels somewhat familiar. I’ve read so much about the Key West Historic District. In fact, Old Town has hosted many famous people, past and present. Some notable residents include author Ernest Hemingway, singer-songwriter Jimmy Buffett, author Judy Blume, and former US president Harry S. Truman. Parrot heads, as Jimmy Buffet fans are called, flock to Old Town Key West every year to pay homage to their musical hero. It’s one of the most popular tourist destinations in Florida, and I can see why. From a bustling nightlife to tranquil beaches, from museums to an array of local restaurants serving up delicious seafood, there is something for everyone here. It’s easy to see why singers, song writers, and authors find such inspiration here!

jimmy buffet, singer, guitarist

My First Experience with Duval Street

 

 My first time in this beautiful town was a day trip by plane. I was working on my private pilot’s license and my instructor suggested we fly to Key West. Sure! Our small 4-seater plane flew over the keys and landed smoothly at the Key West International Airport. We had chosen a beautiful spring day for our trip, giving us a fantastic view of the keys as we flew. The water surrounding the land sparkled in the Florida sunshine. Our excitement built as we got a ride to downtown Key West for our trip. Exploring Old Town gave me more of a perspective on why writers and entertainers choose to vacation or even live here. I found the inspiration to write almost overwhelming! I’ll be writing more on our day trip in a future article. For now, I’d like to touch on some of this region’s fascinating points.

 

Introduction to Old Town Key West

 

Old Town Key West occupies the westernmost point of the Florida Keys. Most know this area for its rich history, vibrant culture, and stunning natural beauty. This charming neighborhood is home to some of the most well-preserved architecture in the country. In fact, many buildings date back to the 1800s.

butterfly, butterfly sanctuary, key west

Best Restaurants in Old Town Key West

Old Town Key West is home to some of the country’s best restaurants, with various options to suit every taste and budget.

 

One of the top spots for seafood is A&B Lobster House, which offers fresh seafood dishes and stunning harbor views. For a casual dining experience, head to Blue Heaven, known for its delicious breakfast and brunch dishes.

Other top restaurants in Old Town Key West include Café Marquesa, which serves contemporary American cuisine, and El Meson de Pepe, known for its authentic Cuban dishes.

 

Old Town Key West Nightlife

 

Old Town Key West comes alive with a vibrant nightlife scene when the sun goes down. There are plenty of bars and clubs to choose from, with something to suit every taste.

 

One of the most popular spots for live music is the Green Parrot Bar, which has been a fixture in Old Town Key West since the 1890s. For a more laid-back atmosphere, head to the Schooner Wharf Bar, which offers stunning views of the harbor and live music every night.

Other top nightlife spots in Old Town Key West include the Bull and Whistle Bar, known for its lively outdoor patio, and the Smokin’ Tuna Saloon, which offers a variety of live music performances.

Accommodations in Old Town Key West 

Old Town Key West is home to various accommodations, from cozy bed and breakfasts to luxurious resorts.

For a truly unique experience, consider staying at the Casa Marina, a historic hotel that dates back to the 1920s. This stunning property is located right on the beach and offers a variety of amenities, including a spa and a private beach.

Other top options for accommodations in Old Town Key West include the Marquesa Hotel, located in the heart of Old Town Key West and offers a peaceful retreat, and the Southernmost Beach Resort, known for its stunning ocean views and luxurious amenities.

Key Landmarks and Attractions in Old Town Key West

 

key west, florida, tropical

 

 

In addition to the must-visit attractions mentioned above, there are a number of other landmarks and attractions that are worth checking out in Old Town Key West.

 One of these is the Key West Art and Historical Society, which is dedicated to preserving and promoting the history and culture of Key West. Visitors can explore a variety of exhibits, including art collections and historic artifacts.

 Another top attraction is the Harry S. Truman Little White House, which was once the winter home of President Truman. Visitors can take a guided tour of the house and learn more about Truman’s life and presidency.

 

Exploring the Famous Duval Street in Old Town Key West

 

As mentioned earlier, Duval Street is one of the most famous landmarks in Old Town Key West. This vibrant street is home to a variety of shops, restaurants, and bars, as well as a number of historic landmarks.

One of the top attractions on Duval Street is the Key West Butterfly and Nature Conservatory, which was mentioned earlier. This beautiful indoor garden is a peaceful oasis in the heart of the city, and is a must-visit for nature lovers.

Another popular spot on Duval Street is the Key West Historic Seaport, which was also mentioned earlier. This charming marina is a great place to grab a bite to eat or enjoy a sunset sail.

 

The Unique Architecture of Old Town Key West

 

One of the most striking things about Old Town Key West is its unique architecture. The city is home to various colorful, wooden houses, many of which date back to the 1800s.

One of the most iconic architectural styles in Old Town Key West is known as the “conch” style. This style is characterized by steeply pitched metal roofs and a unique floor plan allowing maximum ventilation and natural light.

Other notable architectural styles in Old Town Key West include the Victorian style, characterized by ornate details and decorative trim, and the Bahamian style, characterized by bright colors and breezy, tropical design elements.

Video Credit: @KarriannGraf

Food and Drink Options in Old Town Key West

When it comes to food and drink, Old Town Key West has something to suit every taste and budget. In addition to the top restaurants mentioned earlier, there are plenty of other options.

One popular spot for cocktails is the Sunset Pier, which offers stunning ocean views and a variety of signature drinks. For a more laid-back atmosphere, head to the Hog’s Breath Saloon, which is known for its live music and casual vibe.

Other top spots for food and drink in Old Town Key West include the Conch Republic Seafood Company, known for its fresh seafood dishes, and the Sloppy Joe’s Bar, a classic Key West institution.

 

Accommodation Options in Old Town Key West  

beach, key west, florida

 

 As mentioned earlier, Old Town Key West is home to a variety of accommodations, from cozy bed and breakfasts to luxurious resorts.

One popular option for those looking for a unique experience is the island’s many guesthouses. These cozy properties offer a more intimate experience than traditional hotels, and often include amenities like private pools and outdoor spaces.

Other top options for accommodations in Old Town Key West include the Marquesa Hotel, which was mentioned earlier, and the Ocean Key Resort and Spa, which offers stunning ocean views and a variety of luxurious amenities.

Tips for Visiting Old Town Key West 

key west, florida, florida keys

 

If you’re planning a visit to Old Town Key West, there are a few tips to keep in mind to ensure that you have a great experience.

One of the most important things to remember is to stay hydrated. The Florida sun can be intense, especially during the summer, so drink plenty of water and take breaks in the shade when possible.

Another tip is to plan your activities ahead of time. While there is plenty to see and do in Old Town Key West, it’s a good idea to have a general itinerary in mind to ensure you get all the must-see attractions.

Finally, be sure to pack comfortable shoes. Old Town Key West is a very walkable neighborhood, and you’re likely to do a lot of exploring on foot.

 

Old Town Key West Museums and Cultural Institutions

 

In addition to the Key West Art and Historical Society and the Harry S. Truman Little White House, there are a number of other museums and cultural institutions in Old Town Key West that are worth checking out.

One is the Key West Museum of Art and History at the Custom House. This beautiful building was once used as a customs house and now houses various exhibits on the history and culture of Key West.

Another top museum is the Key West Shipwreck Museum, which is dedicated to the history of shipwrecks and treasure hunting in the area. Visitors can see artifacts from some of the most famous shipwrecks in history and learn more about the art of wreck diving.

Old Town Key West Shopping

key west, hemingway house, florida

 If you’re a fan of shopping, Old Town Key West has plenty to offer. In addition to the shops and boutiques on Duval Street, there are a number of other shopping destinations in the area.

One of the top spots for unique, handmade goods is the Key West Artisan Market, which takes place every other Sunday at the Truman Waterfront. Visitors can browse a variety of handmade crafts, jewelry, and other goods, as well as enjoy live music and food vendors.

Another popular destination for shopping in Old Town Key West is the Key West Historic Seaport. This charming marina is home to a variety of shops and boutiques, as well as a number of historic vessels.

 

Old Town Key West Events and Festivals

Throughout the year, Old Town Key West is home to a variety of events and festivals. One of the most popular is the Key West Fantasy Fest, which takes place every October and features a variety of parades, parties, and other festive events.

Other popular events in Old Town Key West include the Hemingway Days Festival, which celebrates the life and work of Ernest Hemingway, and the Key West Food and Wine Festival, which offers a variety of tastings, seminars, and other food-related events.

Old Town Key West Is a Must-Visit Destination

 

In conclusion, Old Town Key West is a truly unique and fascinating destination. From its rich history and vibrant culture to its stunning natural beauty and unique architecture, there is something for everyone here.

 

Whether you’re looking to explore the city’s museums and cultural institutions, relax on the beach, or enjoy the vibrant nightlife scene, Old Town Key West has it all. So why not plan your visit today and discover all that this incredible neighborhood has to offer?

Despite its small size, Old Town Key West always offers a lot to visitors. From its world-famous Duval Street to its picturesque beaches and fascinating museums, there is something for everyone here. Whether you’re a history buff, a foodie, or just looking for a relaxing getaway, Old Town Key West makes the perfect destination.

Historical Significance

Old Town Key West has a fascinating history that spans back to the early 1800s. Initially settled by the Calusa and Tequesta tribes, the area was later claimed by the Spanish and used as a base for smuggling and piracy.

In the early 1800s, the United States established a naval base in Key West. This helped bring prosperity to the area. The city quickly became a hub for trade and commerce, with ships from all over the world stopping in Key West to take on supplies.

During the Civil War, Key West played a vital role as a Union stronghold. It became home to many of the Union’s naval vessels. The city also served as a safe haven for refugees fleeing from the war-torn South.

Today, Old Town Key West is a living testament to this rich history, with many of its historic buildings and landmarks still standing.

Duval Street Key West

No visit to Old Town Key West is complete without a stroll down Duval Street. You just must see this area for yourself! This world-famous stretch of road is home to some of the city’s best restaurants, bars, and shops. You’ll also find a number of historic landmarks.

One of the most iconic landmarks on Duval Street is the Ernest Hemingway Home and Museum. This beautiful property was once the home of the famous author, and is now open to the public as a museum. Visitors can take a tour of the house and learn more about Hemingway’s life and work.

Another must-visit attraction on Duval Street is the Key West Butterfly and Nature Conservatory. Hundreds of exotic butterflies, as well as a variety of birds and plants, make their home in this beautiful garden. Visitors stroll through the garden and enjoy the peaceful surroundings. You may also take part in one of the daily butterfly releases.

Top Things to Do

 

In addition to exploring Duval Street, you’ll find plenty of other things to see and do in Old Town Key West. Some of the top attractions include when you visit Key West:

  • Mel Fisher Maritime Museum: Dedicated to the history of maritime exploration and treasure hunting, the Mel Fisher Maritime Museum is truly fascinating. Visitors view artifacts from some of the world’s most famous shipwrecks. They learn more about the history of diving, too. We spent quite a bit of time here. But it was hardly enough to take everything in. We plan to go back for more treasure hunting!
  • Key West Lighthouse: This historic lighthouse dates back to the 1800s, and offers stunning views of the surrounding area. Visitors can climb to the top of the lighthouse and take in the panoramic views of Old Town Key West. I love lighthouses and this one did not disappoint. Be sure to visit and take in that gorgeous view!
  • Key West Cemetery: This unique cemetery is home to some of the city’s most colorful characters. Visitors can take a self-guided tour of the cemetery and learn more about the history of Key West.
lighthouse, florida, key

Must-Visit Attractions

 

Southernmost point Buoy

While there are plenty of things to see and do in Old Town Key West, a few must-visit attractions should be at the top of every visitor’s list.

One of these is the Southernmost Point Buoy. Located at the southernmost point of the continental United States, this colorful buoy is a popular spot for photos. Visitors can snap a picture with the buoy and take in the stunning views of the ocean.

Another must-visit attraction is the Key West Historic Seaport. This charming marina is home to various restaurants and shops, as well as a number of historic vessels. Visitors can take a sunset sail, go fishing, or stroll around and enjoy the atmosphere.

    key west, boat, party

    Old Town Key West Walking Tour

     One of the best ways to explore Old Town Key West is on foot. There are a number of walking tours available, which offer a fascinating glimpse into the city’s history and culture.

    One popular tour is the Ghosts and Gravestones tour, which takes visitors on a spooky journey through Key West’s haunted past. Another popular option is the Conch Tour Train, which offers a narrated tour of the city’s most famous landmarks.

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    Frequently Asked Questions

    What's the best way to explore Old Town Key West?

    Well, there are a few options depending on your preferences! You could rent a bike and pedal your way around the historic streets, or hop on a trolley tour to see the sights without breaking a sweat. Walking is also a great option, especially if you want to take things slow and soak up the ambiance.

    Are there any must-see attractions in Old Town Key West?

    Absolutely! You won’t want to miss the Ernest Hemingway Home and Museum, where you can see where the famous author lived and worked. The Key West Lighthouse and Keeper’s Quarters Museum is another highlight, offering stunning views of the island from the top.

    Is Old Town Key West family-friendly?

    Yes, absolutely! There are plenty of activities for kids of all ages, from the interactive exhibits at the Key West Aquarium to the pirate-themed adventures at the Mel Fisher Maritime Museum. And with its laid-back atmosphere and friendly locals, Old Town Key West is a great place for families to relax and make memories.

    Is Old Town Key West a good place to stay?

    Definitely! With its historic charm and proximity to all the best attractions, Old Town Key West is the perfect place to base yourself for a vacation on the island. There are plenty of options for accommodations, from cozy guesthouses to luxury hotels.

    What's the food scene like in Old Town Key West?

    Delicious, of course! There are plenty of options for seafood lovers, with everything from fresh oysters to Key West pink shrimp on offer. If you’re looking for something a little more upscale, there are also plenty of fine dining options available.

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