Walking tours in Key West pack centuries of history, local flavors, and island culture into compact, enlightening strolls. The Historic Seaport Food & Walking Tour stands out for its perfect blend of seafaring tales and fresh catch tastings, while the Southernmost Ghosts tour brings the island’s spooky past to life after dark. These well-organized walks typically last between 90 minutes and 3 hours, keeping groups intimate for better interaction with guides. A personal favorite is the Southernmost Food & Cultural tour – it’s the ideal introduction to Key West’s melting pot of Cuban, Caribbean, and Conch influences. Let’s explore the best tours worth your time and money in America’s southernmost city.
Key Points
- Key West offers a variety of highly-rated walking tours, including historical, cultural, culinary, and haunted experiences, with small group sizes and personalized attention.
- Historical tours cover must-see landmarks, shipwrecks, and literary history, while culinary tours showcase local eateries and regional specialties.
- Haunted walking tours explore the city’s paranormal sites and bizarre histories, providing engaging stories and insights.
- Hemingway’s Key West tour delves into the famous author’s life and creative process, highlighting his influence on the local culture.
- Walking tours in Key West typically range from 90 minutes to 3 hours, with many accessible for wheelchair and stroller users.
Historic Seaport Food & Walking Tour by Key West Food Tours
Although Key West is known for its stunning beaches and vibrant nightlife, the Historic Seaport Food & Walking Tour by Key West Food Tours offers visitors a chance to explore the island’s rich culinary and cultural heritage.
This highly-rated tour takes guests on a leisurely stroll through the Historic Seaport, where they’ll indulge in tastings at 5 local eateries. The knowledgeable guides share insights into Key West’s history and traditions as participants savor regional specialties like fish tacos, Cuban sandwiches, and key lime pie.
With a maximum group size of 12, the tour provides an intimate and personalized experience suitable for all ages and mobility levels, making it an ideal way to discover the flavors and stories of this unique Florida destination.
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Key West: Southernmost Ghosts Haunted Walking Tour
For those seeking a spookier side of Key West, the Key West: Southernmost Ghosts Haunted Walking Tour offers a captivating exploration of the island’s haunted history.
At $26 per person and lasting an hour, this tour guides visitors through eight haunted sites, including the Amsterdam Curry Mansion Inn, the Hotel that enchanted Ernest Hemingway, and the La Concha Hotel where victims are said to have jumped.
Led by knowledgeable guides, the tour delves into the chilling tales of local figures, from a jealous pastor to a vindictive wife.
With free cancellation and a meeting point at the Amsterdam Curry Mansion Inn, this haunted walking tour provides a unique and thrilling experience for those interested in Key West’s paranormal past.
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Southernmost Food & Cultural Walking Tour by Key West Food Tours
The Southernmost Food & Cultural Walking Tour by Key West Food Tours provides a comprehensive introduction to the island’s vibrant culinary and cultural scene.
With over 1,300 positive reviews, this small-group tour showcases the best of Old Town’s local eateries and historic landmarks. Guests can expect to sample seafood, Cuban cuisine, and the signature key lime pie while learning about the area’s architecture and history.
The tour covers 1.2 miles and includes four food tastings and one alcoholic beverage.
Wheelchair-accessible and suitable for most fitness levels, this experience offers a personalized look at Key West’s unique character through its diverse flavors and stories.
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Key West: Self-Guided Old Town Treasures Walking Tour
Visitors to Key West’s vibrant Old Town can explore the area’s rich history and charming architecture at their own pace with the self-guided Old Town Treasures Walking Tour.
This activity allows travelers to discover the neighborhood’s historic landmarks, including the Key West Shipwreck Museum and Ernest Hemingway Home and Museum.
The tour covers approximately 1.5 miles and can be completed in 1.5-2 hours. Along the way, participants can admire the colorful, well-preserved architecture and learn about Key West’s unique culture and history.
With the flexibility to explore at their own rhythm, visitors can fully enjoy the charm of Old Town and its many hidden treasures.
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Key West Historic Homes and Island History – Small Group Walking Tour
Nestled in the heart of Key West’s historic district, the Key West Historic Homes and Island History – Small Group Walking Tour provides an intimate and engaging exploration of the city’s architectural treasures and captivating past.
Led by knowledgeable local guides, this 2-hour tour takes visitors on a journey through the island’s unique historical sites, including the Casa Antigua, Curry Mansion Inn, and Truman Annex Park.
With a maximum group size of 10, the tour offers a personalized experience, allowing guests to explore the stories that shaped Key West’s vibrant culture.
Featuring well-preserved historic homes and immersive commentary, this walking tour is a must-do for anyone seeking to connect with the rich heritage of this iconic Florida destination.
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Dark Corners of Key West – Walking Tour
Darkness cloaks the historic streets of Key West on the Dark Corners of Key West – Walking Tour.
This 2-hour exploration takes you through the town’s haunted sites and bizarre histories, with a maximum of 4 participants. For ₹29,416 per group, you’ll uncover the chilling pasts of landmarks like the Dean-Lopez Funeral Home and La Concha Hotel.
Discover the twisted tale of Enriquetta at Marrero’s Guest Mansion and explore the mysteries of Captain Watlington’s Haunted House.
The tour culminates at the Audubon House and Capt Tony’s Saloon, revealing their dark legacies.
With a live English-speaking guide, this walking tour offers a thrilling glimpse into Key West’s sinister side.
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The Ghosts of Key West Walking Tour
Intrigued by the sinister tales of Key West’s past, travelers can embark on The Ghosts of Key West Walking Tour. Rated 4.5 stars with a Badge of Excellence, this 2-hour walking tour brings guests face-to-face with the island’s haunted history.
Led by local, professional guides, the tour visits eerie locations like The Ott House and the infamous purple house with Robert the Doll. Though not recommended for those with back problems or pregnant travelers, the moderate fitness level required is accessible to most.
With knowledgeable and engaging guides like Mike, Erik, and Christian, the tour offers a spooky alternative to Key West’s typical nightlife and a unique way to experience the city’s darker side.
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Key West: History and Culture Southernmost Walking Tour
Discover the rich history and vibrant culture of Key West’s southernmost area on this captivating 1.5-hour walking tour.
Led by knowledgeable local guides, you’ll explore the island’s fascinating past, from its shipwrecking and sponge harvesting industries to its cigar manufacturing heritage.
As you stroll through the southernmost region, you’ll gain a deeper appreciation for Key West’s unique character.
The tour culminates at the iconic Southernmost Point buoy, providing you with maps to continue your independent exploration.
At just $39.99 per person, this exceptional value includes free cancellation up to 24 hours in advance.
Don’t miss this chance to learn about the storied past and present of this captivating destination.
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Key West Walking Food Tour With Secret Food Tours
Stepping away from the historical exploration, visitors to Key West can embark on a culinary journey through the island’s vibrant food scene with the Key West Walking Food Tour by Secret Food Tours.
This highly-rated, 95% recommended tour showcases authentic local cuisine, including Cuban dishes, fresh baked cake, conch fritters, and more. Guests will explore charming neighborhoods, discover lesser-known eateries, and enjoy a friendly atmosphere as they sample the flavors of Key West.
While some critiques mention long wait times and limited historical context, the tour generally receives positive feedback for its enthusiastic guides and delicious food experience.
Priced at $98.10 per person, the tour offers a convenient departure and flexible cancellation policy.
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Key West: Southernmost Food and Cultural Walking Tour
The Key West: Southernmost Food and Cultural Walking Tour offers visitors a delightful opportunity to enjoy the vibrant culinary and historical tapestry of this enchanting island.
This 3-hour tour, limited to just 7 participants, takes guests on a journey through Key West’s historic neighborhoods, where they’ll indulge in 5 local delicacies, including conch fritters and key lime pie.
Led by a knowledgeable local guide, the tour provides an insider’s perspective on the city’s rich cultural heritage.
Participants receive exclusive recipes and dining recommendations, as well as shopping coupons, making this an exceptional value.
With a 4.8/5 overall rating from 63 reviews, this tour is a must-do for anyone seeking an authentic taste of Key West.
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Old Town Key West Literary Walking Tour
Visitors exploring the charming streets of Old Town Key West can embark on the captivating Old Town Key West Literary Walking Tour. This 90-minute walking tour covers one mile, exploring the homes of past and current writers, sharing snippets of their work, and highlighting Key West landmarks.
Led by knowledgeable and personable guides, the tour provides an informative and engaging experience, with positive feedback on the storytelling and visual aids. While most participants find the moderate fitness level manageable, some older travelers may struggle to keep pace.
The tour is wheelchair and stroller accessible, and operates in all weather conditions, making it an excellent choice for literary enthusiasts visiting Key West.
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Florida Keys: Self-Guided Driving and Walking Audio Tour
For those seeking a convenient and comprehensive way to explore the Florida Keys, the self-guided Florida Keys: Driving and Walking Audio Tour provides an immersive experience.
Designed for both drivers and pedestrians, the tour guides you through the stunning scenery and rich history of the Keys. With the GPS-enabled audio, you’ll learn about the region’s unique ecology, cultural attractions, and local lore as you navigate the scenic routes.
Whether you’re cruising down the Overseas Highway or strolling through charming neighborhoods, this tour offers a seamless and enriching way to discover the wonders of the Florida Keys at your own pace.
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Highlights and Stories of Key West – Small Group Walking Tour
Participants on the Highlights and Stories of Key West – Small Group Walking Tour embark on an engaging exploration of the island’s captivating history, vibrant culture, and natural wonders.
Led by knowledgeable local guides like Richard, this 2-hour walking tour takes visitors to iconic landmarks, including the Audubon House and the Southernmost Point.
With a maximum group size of 10, the tour offers a personalized experience, complete with storytelling and historical insights.
Rain ponchos, umbrellas, and bottled water are provided, and the tour is wheelchair and stroller accessible.
Highly recommended for visitors seeking an introductory immersion in the unique charm of Key West.
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Southernmost Key West History and Culture Small-Group Walking Tour
The Southernmost Key West History and Culture Small-Group Walking Tour offers visitors an immersive exploration of the island’s captivating past and vibrant present.
Led by knowledgeable local guides, this 92-review, 99%-recommended tour covers the must-see landmarks of Old Town Key West, including the Ernest Hemingway Home and Museum, the Southernmost Point, and the Audubon House & Tropical Gardens.
Participants will explore the city’s rich history, learning about shipwrecks, cigar manufacturing, and treasure hunting.
With a moderate pace and distance, the tour is accessible to most visitors, though not wheelchair-friendly.
Priced at $39.99 per person, the experience offers excellent value and a great introduction to the unique culture and charm of Key West.
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Florida Keys: Self-Guided Walking Tour
Exploring the Florida Keys on a self-guided walking tour offers visitors a unique opportunity to enjoy the region’s vibrant culture and natural beauty at their own pace.
This flexible tour allows travelers to discover the highlights of Key West, including Mallory Square, the Key West Shipwreck Museum, and the Ernest Hemingway Home and Museum.
Visitors can stroll along the lively Duval Street, a popular gathering place to witness the stunning sunset over the Gulf of Mexico.
With no set itinerary, travelers can tailor their experience to their interests, from exploring cultural attractions to enjoying outdoor activities like sailing, snorkeling, or jet skiing.
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Key West Historic District Small-Group Walking Tour
Although Key West is known for its vibrant nightlife and laid-back island atmosphere, the city’s historic district offers visitors a chance to explore its storied past.
The Key West Historic District Small-Group Walking Tour provides an intimate and informative experience, with a maximum of 10 guests ensuring a crowd-free exploration. Over the course of 2 hours, a knowledgeable guide leads participants through 1.4 to 1.8 miles, highlighting landmarks, architecture, and cultural influences.
Guests praise the guides’ extensive knowledge and engaging storytelling, as well as the personal attention afforded by the small group size. While some wish for water during the tour, the experience is highly recommended for both newcomers and repeat visitors to Key West.
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Key West: Food Tasting and Cultural Walking Tour
Embarking on the Key West: Seafood and Seaport Walking Tour, visitors enjoy the city’s vibrant culinary landscape and rich cultural heritage.
Over 3 hours, the guided tour takes guests to 6 local eateries and family restaurants, offering tastings that make for a hearty lunch.
Participants explore Key West’s Historic Seaport, learning about the island’s industrial history and architectural charm while capturing photos of its flora, murals, and landmarks.
The tour’s highlight is discovering the region’s culinary traditions, including the iconic conch.
With a small group of up to 7 people, the experience ensures an intimate and personalized exploration of Key West’s food and culture.
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Hemingway Food and Walking Tour
The Hemingway Food and Walking Tour in Key West promises an immersive exploration of the iconic writer’s life and legacy in the city he called home during the 1920s and 1930s.
This 2-hour tour takes travelers on a journey through Key West, stopping at the Hemingway Home and Museum and Capt Tony’s Saloon. Guided by local experts, the tour offers a blend of culinary delights and historical insights, with a sample menu including chicken street tacos, conch fritters, and the renowned Key lime pie.
While the food options may be limited for some, the engaging and entertaining experiences reported by travelers make this tour a compelling choice for history buffs and foodies alike.
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Best of Key West Walking Tour With Glass Bottom Boat Cruise
This comprehensive walking tour of Key West’s highlights offers an immersive experience, culminating in a glass bottom boat cruise that allows visitors to marvel at the vibrant marine life beneath the waves.
Exploring the city’s top sights, including Mallory Square, the Key West Shipwreck Museum, and the Ernest Hemingway Home and Museum, the tour provides an in-depth look at the island’s rich history and culture.
Guests can expect to enjoy a leisurely pace, with ample opportunities to capture stunning photographs and savor the local flavors, such as the iconic Key lime pie.
Whether seeking a deeper understanding of Key West or simply wanting to experience its natural beauty, this walking tour is an excellent choice.
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Key West: Hemingways Life and Local Food Walking Tour
Guests on the Key West: Hemingway’s Life and Local Food Walking Tour can expect an immersive exploration of the beloved author’s time in the island city.
The 2-hour guided walking tour takes visitors to significant landmarks related to Hemingway’s life, including his former residence and favorite local haunts.
Along the way, you will enjoy three food tastings featuring grilled chicken street tacos, conch fritters, and key lime pie.
The tour also covers Hemingway’s experiences in Key West, from fishing and boxing to writing “A Farewell to Arms.”
With a price of $99 per person and free cancellation up to 24 hours in advance, this tour provides an engaging and affordable way to discover Hemingway’s legacy in Key West.
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Frequently Asked Questions
Can I Bring My Pet on the Walking Tour?
Most walking tour providers allow guests to bring their pets, but it’s best to check with the specific tour company beforehand. Some may have restrictions or require pets to be leashed for the safety and comfort of all participants.
Are the Tours Wheelchair Accessible?
Many walking tours are wheelchair accessible, but it’s best to check with the tour operator beforehand. They can provide details on accessibility and make accommodations to ensure everyone can participate fully in the tour.
How Much Time Should I Allocate for Each Tour?
Depending on the tour, visitors should plan to spend 1-2 hours exploring the sights. Shorter tours may last around an hour, while more comprehensive ones can take up to 2 hours to complete. The pace is usually relaxed, allowing time to take in the surroundings.
Do the Tours Provide Water or Snacks?
Most walking tours don’t provide water or snacks, so it’s best to bring your own. Staying hydrated and fueled is important, especially in hot or humid conditions. Some tours may offer these amenities, but it’s wise to double-check before booking.
What Is the Cancellation Policy for the Tours?
The cancellation policy typically allows for full refunds if you cancel at least 24-48 hours in advance. Many tours also offer flexible rescheduling if you can’t make the original date.
The Sum Up
Whether you’re interested in history, food, or the paranormal, Key West offers a variety of walking tours to suit your interests. From exploring the city’s historic seaport to discovering its haunted past, these tours provide an engaging and immersive way to experience the unique charm of this island destination. With so many options, there’s sure to be a walking tour that’ll make your visit to Key West unforgettable.