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38 results | All Key West Tours

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Key West Southernmost Food and Cultural Walking Tour

Key West Southernmost Food and Cultural Walking Tour

star-5
558
Eat your way around Key West on this food tour with a guide who introduces you to 'mom and pop' eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and, of course, key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.
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  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Key West Historic Seaport Food Tasting and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
265
Taste your way through Key West's Historic Seaport on a gourmet walking tour with a local guide. You'll stroll from the beach and docks into some of the most colorful neighborhoods in Key West, pausing to sample locally-caught fish tacos, Key West pink shrimp, spiny lobster, or other just-as-delicious non-seafood options, learning about Key West history along the way. Don't forget to save room for a refreshing glass of white wine and our famous key lime pie! Exploring Key West on foot is an ideal way to soak up the vibrant atmosphere, and group size is limited to 10 people to ensure personal service from your guide.
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  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Key West Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
189
Experience Key West’s dark side on this fun yet frightening haunted bar crawl. Hear tales of known paranormal activity from your local guide and visit the most eerie bars in Old Town Key West – located in two haunted mansions and repurposed morgue. By the end of the 2‐hour tour, you’ll see ‘Bone Island’ in a different (and profoundly spookier) light.
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  • 2 hours
  • Free Cancellation
From
$26.82
From
$26.82

Guided Bicycle Tour of Old Town Key West

Guided Bicycle Tour of Old Town Key West

star-5
1267
Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.
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  • 3 hours
  • Free Cancellation
From
$49.81
From
$49.81

Key West Ghost and Mysteries Guided Tour

Key West Ghost and Mysteries Guided Tour

star-4.5
814
Discover the spooky side to one of the country's most haunted cities on a 90-minute walking tour. Listen to hair-raising local legends as you follow your guide down the hidden alley's of Key West. See where Robert the Doll lived, learn about Count Von Cosel, and keep your eyes peeled for the ghost at La Concha. Learn how to attract spirit activity with dowsing rods and how to capture it with your camera.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$32.26
From
$32.26

Key West Ghosts and Gravestones Trolley Tour

Key West Ghosts and Gravestones Trolley Tour

star-4
323
Discover some of Key West’s deepest, darkest secrets on a 60-minute ghost-themed trolley tour. The Trolley of the Doomed explores the darker side of one of the most haunted cities in the country. Experience Key West’s frightening past while traveling down the narrow, dark streets of Old Town, lined with 19th-century wooden houses that still bear the secrets of their former inhabitants. This tour is narrated by a 17th-century gravedigger guide who’s almost as scary as the stories being shared.
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  • 1 hour
  • Free Cancellation
From
$38.80
From
$38.80

Key West Historic District Small-Group Walking Tour

Key West Historic District Small-Group Walking Tour

star-5
31
Rich in history and culture, Key West's Historic District demands to be explored in the company of someone who knows its stories. This small-group walking tour promises a far richer experience than wandering around alone. As you stroll through the scenic streets, your guide will fill you in on Key West's history, lore and legends.
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  • 2 hours
  • Free Cancellation
From
$46.99
From
$46.99

Key West Craft Cocktail Crawl
Likely to Sell OutLikely to Sell Out

Key West Craft Cocktail Crawl

star-5
150
Explore Key West through the eyes of a local on a craft cocktail tour that stops at five off–the–beaten–path establishments, from a historic mansion to a boutique hotel that was once a hospital. In addition to navigating for you, your guide uses the city’s bar scene to give you an overview of its history and culture. The tour includes five craft cocktails and two gourmet food tastings.
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  • 3 hours
  • Free Cancellation
From
$93.68
From
$93.68

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
Likely to Sell OutLikely to Sell Out

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

star-4.5
1157
Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.
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  • 2 hours
  • Free Cancellation
From
$89.95
From
$89.95

Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
548
Explore the best that Key West has to offer on this narrated, hop-on hop-off trolley tour. Visit more than 100 points of interest among Key West’s top attractions, with an expert guide who takes you through the history of the city. Select from an unlimited 1- or 2-day pass to suit your schedule.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$50.35
From
$50.35

Key West Florida Reef Half-Day Snorkeling Excursion

Key West Florida Reef Half-Day Snorkeling Excursion

star-4.5
708
Enjoy an afternoon of swimming and snorkeling on this cruise off the coast of Key West. Spend a relaxing afternoon on a 69-foot catamaran headed to North America's only living coral barrier reef for the adventure of a lifetime. Pass some of Key West’s top attractions on the way, then dive right in to see more than 600 species of colorful fish, coral, and other sea life. This cruise includes professional snorkeling gear and instruction plus beer, wine, and soft drinks.
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  • 3 hours
  • Free Cancellation
From
$45.95
From
$45.95

Key West Pub Crawl

Key West Pub Crawl

star-4.5
167
Get ready to party in paradise on this guided, 2.5-hour Key West pub crawl. The beautiful island city of Key West is famous for its raucous bar scene. Visit some of its most popular and entertaining establishments, beginning downtown and then traveling to the historic seaport and back to busy Duval Street. Enjoy a domestic beer or mixed drink at each of the five locations and receive a free souvenir t-shirt to commemorate the event. Guests must be at least 21 years old to participate.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$37.57
From
$37.57

Southernmost Key West History and Culture Small-Group Walking Tour
Likely to Sell OutLikely to Sell Out

Southernmost Key West History and Culture Small-Group Walking Tour

star-5
53
Explore the streets of Key West on this guided small-group walking tour. As you wander through Old Town, discover the history and culture of the island, which includes tales of shipwrecks, cigar manufacturing, and treasure hunting. Stop at popular attractions such as the Ernest Hemingway Home and Museum, the Southernmost Point, and Audubon House & Tropical Gardens.
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  • 1 hour 45 minutes
  • Free Cancellation
From
$39.99
From
$39.99

Key West Historic Homes and Island History - Small Group Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Historic Homes and Island History - Small Group Walking Tour

star-5
68
Key West is home to many unique architectural landmarks and historic homes. Rather than wandering around alone, you can learn the fascinating stories of each by taking a guided tour. This small-group walking tour provides in-depth insights into the people and places of historic Key West.
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  • 2 hours
  • Free Cancellation
From
$45.00
From
$45.00

Easy Stroll Through Downtown Key West Audio Tour

Easy Stroll Through Downtown Key West Audio Tour

star-4.5
3
Turn your phone or tablet into a local tour guide! Download this location-aware audio & multimedia tour to your device. Local knowledge, historic photos, and links to websites and restaurant menus rest at your fingertips. In just an hour of easy walking, learn the history, culture, and cuisine of Key West, never wasting a step. Visit the most important museums and attractions. Discover the island’s best Key lime pie, Cuban cigars, rum mojitos, craft beer, conch ceviche, fish tacos, and handmade sandals. Learn about famous writers, wreckers, and pirates. End with a swim on a popular beach. Perfect for solo travelers and small groups. Sight-see at your own pace, avoid being herded in a big crowd and only linger in the places that truly interest you. Soon after booking, you'll receive an email with a login instructions and a coupon code allowing you to access your tour.
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  • 1 hour
From
$9.99
From
$9.99

PRIVATE Welcome to Key West Walking Tour

PRIVATE Welcome to Key West Walking Tour

star-5
9
This private tour is ideal if you want to see it all in Key West, but are not a fan of crowded group tours. In the company of just your group and a guide, hit the streets and stroll to all the top attractions, including the Southernmost Point and Mallory Square. Best of all, the tour can be customized to your own interests.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
$137.50
Price varies by group size
From
$137.50
Price varies by group size

6th Sense Haunted Tour of Key West
Likely to Sell OutLikely to Sell Out

6th Sense Haunted Tour of Key West

star-4
6
Don’t just listen to tales of paranormal activity, experience it for yourself on a ghost tour of Key West that uses investigative equipment to try and communicate with the spirit world. Exploring under the cloak of darkness heightens the atmosphere of this spooky tour, while wandering around the historic centre of Key West on foot gives you a more intimate glimpse into the area.
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  • 2 hours
From
$26.05
From
$26.05

The Dark Side of Key West Ghost Tour

The Dark Side of Key West Ghost Tour

star-4.5
95
It's easy to find the colorful, fun-loving side of Key West, but takes a little more effort to uncover its darker side. This walking tour offers the chance to see Key West in a completely different light. Your guide takes you to landmarks such as St. Paul's Episcopal Church and Capt. Tony's Saloon while discussing the city's spooky, sometimes grisly, history.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$34.99
From
$34.99

Old Town Key West Literary Walking Tour

Old Town Key West Literary Walking Tour

star-5
56
Explore the literary highlights of Key West during this walking tour, inspired by David A. Kaufelt’s original literary walking tour. An in-the-know guide whisks you around the Old Town to the former homes and favorite haunts of writers that have called the island home, including Shel Silverstein, Tennessee Williams, and Robert Frost. Since this is a small-group tour, you’ll have plenty of time to ask questions, too.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

The Ghosts of Key West Walking Tour

The Ghosts of Key West Walking Tour

star-4.5
45
Key West is rich in spooky history but you need a local's insight to fill you in. This walking tour is focused on the island city's hauntings and ghost tales. As you visit notable spots such as St. Paul's Episcopal Church and the Audubon House and Tropical Gardens, your guide will shed light on prominent figures and the dark history of Key West.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$24.99
From
$24.99

Highlights and Stories of Key West - Small Group Walking Tour
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Highlights and Stories of Key West - Small Group Walking Tour

star-5
48
Key West Highlights and Stories- 2020 and 2021 WINNER "Best Key West Walking Tour" Join our award-winning guides for a wonderful, fun, and informative 2.5 hour stroll through the historic streets of Old Town Key West. Our goal is for you to have a fantastic time as your local guide brings to life the rich and colorful history, legends, points of interest, flora/fauna, and culture that make Old Town Key West unique and famous across the globe. There's something for everyone to enjoy on this fascinating and story-filled look behind the scenes of historic Key West. *Consistently ranked as the top “Highlights Tour” by Keys Tourism Association *Voted Top Tour Guides of North America *Over 20 years experience *Our guides have been featured in many leading publications including Gentry, Conde Nast, Frommer’s Travel Guide, Jetset, Hamptons, Travel Weekly, Private Islands, and USA Today. We look forward to sharing Old Town Key West with you.
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  • 2 hours 15 minutes
  • Free Cancellation
From
$45.00
From
$45.00

Go City: Miami All-Inclusive Pass with 25+ Attractions and Tours

Go City: Miami All-Inclusive Pass with 25+ Attractions and Tours

star-4
39
Go City's Miami All-Inclusive Pass offers you the best choice for maximum savings and flexibility when visiting Miami and South Beach. Choose between a 1-, 2-, 3-, or 5-day pass to best suit your trip, and save up to 50 percent versus paying for individual attraction tickets. Each pass is good for two weeks from first use and gives you access to dozens of activities like a day trip to Key West, an Everglades airboat ride, entry to Miami Seaquarium, and more. Access your pass on a mobile device or print it at home and go. It’s that simple. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for the remaining number of days purchased.
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  • 5 days
From
$63.00
From
$63.00

Beach Day in Key West with Picnic Lunch

Beach Day in Key West with Picnic Lunch

star-5
32
Visit Fort Zachary Taylor Historic State Park on a tour that introduces you to both the history and natural beauty of Key West. Located on the southwestern tip of the island, the park is a relaxing place to spend a few hours snorkeling, sunbathing, and discovering historical sites. This tour provides an easy way to see more of Key West for those short on time.
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  • 3 to 5 hours
  • Free Cancellation
From
$125.00
From
$125.00

Hemingway Food and Walking Tour

Hemingway Food and Walking Tour

star-5
22
This guided walking tour will take you to the real places that Hemingway lived, worked and played, including where he watched and refereed boxing matches, where he kept his boat the Pilar, the bookstore where his books were sold, his first apartment in Key West where he finished writing “A Farewell to Arms”. Along the way you will have three food samplings, before visiting where he took the train, fished and charted boats in the Key West Harbor, and finally where he spent a lot of time drinking- Sloppy Joe's. An alcoholic drink is also included for you to experience Hemingway's favorite bar. Numerous other historical sites that Hemingway frequented while he lived in Key West will also be visited on this incredibly authentic tour.
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  • 2 hours
  • Free Cancellation
From
$88.00
From
$88.00

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What people are saying about Walking Tours in Key West

star-5
Key West Southernmost Food and Cultural Walking Tour
"We had a fabulous time on the food tour hosted by Maxwell. He was a charming host, very knowledgeable of the island and its cultures and was a local which added quite a bit of realism to the tour. Was very informative and talked about a number of other items regarding the island – could not have asked for a better guy"..."
star-5
Key West Historic Seaport Food Tasting and Cultural Walking Tour
"Our tour guide, Sharon, was very friendly and knowledgeable of the sites and foods on our tour! Very good food tour!"..."
star-5
Key West Haunted Pub Crawl and Ghost Tour
"Our guide had lots of stories and seemed knowledgeable about the history of the area. We had fun and enjoyed seeing the bars and homes."..."
star-5
Guided Bicycle Tour of Old Town Key West
"Our your guide was James and he was a very entertaining and informative tour guide. He gave us a lot of historic facts but kept the experience fun!"..."
star-5
Key West Ghost and Mysteries Guided Tour
"Ted did an excellent job. His stories were very interesting!! Would recommend this tour. Our first Ghost Tour. Loved it"..."
star-5
Key West Ghosts and Gravestones Trolley Tour
"Great tour. Very informative, the bus driver was entertaining and did a great job driving. The tour guide was knowledgeable and entertaining as well."..."
star-5
Key West Historic District Small-Group Walking Tour
"Husband and I enjoyed learning about the origins of the Conch Republic as we walked the neighborhoods with friendly and knowledgeable Alejandro."..."
star-5
Key West Craft Cocktail Crawl
"Great time! Love finding out about places off the beaten path! Rose was a great tour guide! Fun and friendly!"..."
star-5
Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres
"Great time with great people and beautiful views! Staff was great at keeping the drinks full! The vibe and atmosphere were fun and relaxed."..."
star-5
Key West Hop-On Hop-Off Trolley Tour
"The only way to see and tour key west. Good history lesson as you ride. Stop at Hemingway House or Butterfly Conservatory or Mallory Square. The only way to be on vacation and tour."..."
star-5
Key West Florida Reef Half-Day Snorkeling Excursion
"Had an amazing time! I read the reviews and was worried. Our water was perfect. Crew fantastic and fun to chat with! Other guests made the day complete."..."
star-5
Key West Pub Crawl
"Mike did a great job! Gave interesting history on the island as well as providing great service. Would definitely recommend it to everyone!"..."
star-5
Southernmost Key West History and Culture Small-Group Walking Tour
"AJ was very knowledgeable about Key West history. His IPad with pictures of old key west was a nice touch! Awesome tour!"..."
star-5
Key West Historic Homes and Island History - Small Group Walking Tour
"Richard is so knowledgeable about Key West. He shows a great deal of enthusiasm even though he presents the same info over & over on a daily basis. The tour is very informative & conducted in an unhurried, relaxed manner. Thanks to Richard for such a great introduction to his hometown."..."
star-5
Easy Stroll Through Downtown Key West Audio Tour
"Enjoyed the commentaries for various sites, such as Hemingway. Great overview after our arrival. Maps included really helpful."..."
star-5
PRIVATE Welcome to Key West Walking Tour
"I was specifically wanting to become more familiar with the layout of the town in a short period. Rick did a great job of tailoring the tour to those expectations. I feel like I can now go or direct others to areas that are of specific interest to me. Thanks so much, Rick! I really liked the local perspectives you gave. Prior to the tour Rick contacted me to find out what I wanted to see and I mentioned seeing the fireworks without hanging out on the beach. He gave information that allowed me to watch the fireworks eating a delicious meal knowing I was contributing to scholarships for high school seniors. It was also nice to meet different people who live on the islands. When the walking tour was over I enjoyed a guided tour that Rick gave in the Truman White House. Probably wouldn’t have done that again but was having such a good day walking and enjoying the island. Great way to explore the island from the Atlantic to the Gulf. I will definitely contact Rick before returning to Key West."..."
star-5
6th Sense Haunted Tour of Key West
"Great tour guide and story teller. Came back to the hotel and I think my entire family was comparing stories."..."
star-5
The Dark Side of Key West Ghost Tour
"We really enjoyed the tour. The history is fascinating. Laura is a great tour guide. It lasts an hour and a half and it's a nice walk around the different haunted locations. We had a nice sized group and i'm happy to see people out and about doing this tour! Book it, great time guaranteed!"..."
star-5
Old Town Key West Literary Walking Tour
"Sarah was terrific! This is the third time I have done this tour and she managed to keep it fresh and entertaining."..."
star-5
The Ghosts of Key West Walking Tour
"The ghost tour company was wonderful in helping fix an error with our booking though Viator. We ended up with a private guide who was great with my large family (14 of us) ages 12 to 80. Her stories got us ‘thinking’ and spurred new conversations the next day. Thank you Lauren!"..."
star-5
Highlights and Stories of Key West - Small Group Walking Tour
"Very engaging and informative 3rd-generation Key Wester host. We learned a lot of fun facts about the history of Key West and it’s residents and how weather events changed them through the years."..."
star-5
Go City: Miami All-Inclusive Pass with 25+ Attractions and Tours
"This is the first real vacation my family has taken in the past 15 years, and I would recommend this card to everyone. The only problem we ran into was not enough hours in the day to do all the things we wanted to do that were available with this card. Worth every penny!"..."
star-5
Beach Day in Key West with Picnic Lunch
"Excellent beach day! Just a little wind but the wind kept it cool (Margaret was great at reaching out and rescheduling our day to avoid rainy weather) Got a little history of Fort Zachary Taylor Lunch was great too Perfect to show up at the beach and have chairs, umbrellas, towels and snorkeling gear ready for us! Would do it again!!"..."
star-5
Hemingway Food and Walking Tour
"Super tour filled with tons of great information on Hemingway’s time in Key West. Mark really brings Hemingway’s life here to light with stops all over Key West. Great additional history on Key West in general. Food stops were a great way to eat a local bit, sit in A/C, and listen to more history. Would highly recommend!"..."

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Walking Tours in Key West?
Q:
What Walking Tours in Key West are taking additional safety precautions?
Q:
What Walking Tours in Key West are good for avoiding crowds?