Key West Walking: Soak in the Sights

There are many ways to explore the paradise that is Key West, but our island’s compact, pedestrian-friendly layout makes the southernmost city in the continental U.S. an ideal destination for walking. A leisurely stroll reveals the island’s charming hidden streets, rich history and fascinating natural features in ways you’d never be able to experience by car. Historic Key West Vacation Rentals puts you in the center of this unique destination. With many of our properties situated in the island’s Historic District, our luxury vacation rental homes provide the ideal jumping off point for exploring all the island’s most alluring features. And our knowledgeable staff is ready to help maximize your experience here with their personal attention. 

Why Key West is ideal for walking
●       Compact layout: At around 4 square miles, Key West is easy to navigate. And most of the island’s attractions are concentrated in the Old Town, so you can explore the island’s highlights within this small area.
●       Scenic beauty: Strolling through Key West offers breathtaking views at every turn. You’ll have the luxury of stopping for photos of turquoise waters with white-sand beaches, lush tropical gardens and charming architecture.
●       Vibrant atmosphere: On foot, you’ll be immersed in the life of the city. You can’t help but be caught up in its street performers, local artists and busy markets. 

Ideas for discovering Key West on foot
Here are some of our favorite walking self-tours that showcase the best of our tropical paradise:
●       Historic Old Town Walking Tour: Begin your journey in the heart of Old Town, where history comes alive through its well-preserved architecture and storied past. Wind your way to Mallory Square, famous for its nightly sunset celebrations. From there, head to the Key West Historic Seaport, a bustling marina with picturesque views and fabulous seafood restaurants. Move onto the Ernest Hemingway Home and Museum on Whitehead Street. This iconic residence offers a glimpse into the life of one of the world’s most renowned authors. Nearby, you’ll find the Key West Lighthouse with its panoramic views of the island from an observation deck. Continue on to the Truman Little White House, where President Harry S Truman spent his winters. This historic site offers guided tours that explain its presidential past. End your tour at the Southernmost Point buoy, a popular photo spot marking the southernmost tip of the continental United States. Don’t forget your camera!
●       Duval Street Stroll: Stretching from the Gulf of Mexico to the Atlantic Ocean, world famous Duval Street is known for its indulgent nightlife, eclectic galleries, boutiques and historical sites. This street boasts one of the densest concentrations of bars in the world, 43 to be exact. Begin your stroll at the northern end near Mallory Square and make your way south. As you walk, you’ll pass St. Paul’s Episcopal Church and the San Carlos Institute, a cultural center dedicated to preserving Cuban heritage. Don’t miss the iconic Sloppy Joe’s Bar, a favorite of Hemingway. The street comes alive in the evening with live music and a wild nightlife scene. Finish your walk at the southern end with a visit to the Ernest Hemingway House or a quiet break at South Beach.
●       Literary Walking Tour: Key West has long been a haven for writers and artists. This tour celebrates the island’s literary history, starting at the Ernest Hemingway Home and Museum. Explore the house and gardens, where Hemingway wrote some of his most famous works. From there, head to the Tennessee Williams Museum on Truman Avenue. Williams spent many years in Key West, and the museum offers insights into his life and works, along with a collection of memorabilia. Continue walking to visit the Key West Library on Fleming Street, which has a dedicated section for local authors. End your tour with a stop at Blue Heaven restaurant, traditionally a popular gathering spot for writers and artists.
●       Art and architecture walking tour: Start in Old Town to experience Key West’s unique architecture and vibrant art scene. Here, charming Conch houses and Victorian mansions, painted in pastel hues and adorned with intricate woodwork, showcase the island’s rich architectural heritage. You’ll see structures such as the Truman Little White House, the Oldest House in South Florida and the Audubon House. Stop at the “eyebrow” house at 512 William Street, named for its upper windows shaded by a roof overhang, a style unique to Key West. Make your way to the Key West Art Center on Front Street, which features works by local artists. Continue to The Studios of Key West, an art space that hosts exhibitions, workshops, and performances. Along the way, you'll encounter numerous galleries and outdoor art installations. Don’t miss the chance to visit the Sculpture Garden in Mallory Square, which features bronze busts of influential Key West figures.
●       Cemetery tour: Perhaps the most memorable walking tour is the historic 19-acre cemetery on Pauline Street in Old Town, known for its eccentricities, pet burials, resident iguanas, the “I Told You I Was Sick” headstone and grand, New Orleans-style family plots with open roof structures and masonry buildings. Through an agreement with the City of Key West, the Historic Florida Keys Foundation offers a tour of the cemetery twice a week. These tours raise funds for Cemetery preservation. In October 2005 the tours were featured nationwide on PBS television’s “Cemetery Special.” Otherwise, admission is free, and a detailed map is available.

Ghost tours
Key West is considered one of the most haunted cities in the United States, with many ghost stories associated with public buildings and private homes. The island's rich history includes pirates, Indians, shipwrecks and buried treasure! Following are fun ghost tours we highly recommend:
●       Ghost & Gravestones Tour: Experience the strange, macabre and unusual side of Key West at night as you embark on a spooky adventure to discover the haunted history of Key West.
●       Key West Ghost & Mysteries Tour: A long-time favorite among visitors, this guided 90-minute walking ghost tour includes stops at the graveyard, Hemingway’s Casa Antigua, and Artist’s House, the original home of the haunted Robert the Doll.
●       The Original Key West Ghost Hunt: Experience the eerie side of the island with this authentic ghost hunt as you walk the shadowy lanes of old town Key West and discover ghosts, ghouls and legends.

Historic Homes and History of Key West
Consistently ranked in the Top 10 History Tours in the United States by TripAdvisor, this excursion offers a 2.25-hour walk through all Key West’s Old Town neighborhoods to take in gorgeous historic homes and the island’s unique architecture. Along the way, you’ll pass important landmarks like the Geiger-Audubon House; Truman’s Little White House; the Presidential Gates; Jesse Porter Heritage House and Robert Frost Cottage; and Casa Antigua, where Hemingway penned his masterpiece “A Farewell to Arms.” You’ll end your tour at the marina, where you can shop and grab lunch.

Staying in a Key West Vacation Home
Choosing a vacation home in Key West enhances your walking adventures by providing a comfortable and convenient base. Our properties blend historic charm with modern amenities, so you’ll enjoy the privacy of your own home, with the convenience of proximity to Key West’s top attractions. Often nestled in the heart of historic neighborhoods and offering easy access to the city, our gorgeous Historic Key West Vacation Rental homes offer your first step into fabulous Key West.

To help plan your trip after booking, consider our Concierge Services. Our team of experienced, friendly and knowledgeable specialists can help elevate your Key West experience. They’ll provide just the right personal touch and assist with your individual needs.