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37 results | All Key West Tours

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Key West Southernmost Food and Cultural Walking Tour
Likely to Sell OutLikely to Sell Out

Key West Southernmost Food and Cultural Walking Tour

star-5
527
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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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* A traveler said: "Our guide, Kayla, and the others on the tour were the favorite parts. The food and visits were great, too. This is my 3rd food tour and it was a wonderful experience."


Key West Historic Seaport Food Tasting and Cultural Walking Tour
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Key West Historic Seaport Food Tasting and Cultural Walking Tour

star-5
238
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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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* A traveler said: "our guide Sharon was very knowledgeable and the food was delicious! The tour takes about 3 hours. Wear comfortable shoes because there is a great deal of walking."


Key West Haunted Pub Crawl and Ghost Tour

Key West Haunted Pub Crawl and Ghost Tour

star-4
168
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$22.62
From
$22.62
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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* A traveler said: "Informative and cool. Kelly was a lot of fun. There seemed to be 20 people signed up, they broke us up into 2 groups which was good."


Guided Bicycle Tour of Old Town Key West

Guided Bicycle Tour of Old Town Key West

star-5
1219
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$49.81
From
$49.81
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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* A traveler said: "Yvonne was amazing very knowledgeable in the history of the Keys and in keeping a timely tour and the key lime pie was amazing!!!!"


Key West Ghost and Mysteries Guided Tour

Key West Ghost and Mysteries Guided Tour

star-4.5
794
  • 1 hour 30 minutes
  • Free Cancellation
From
$32.26
From
$32.26
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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* A traveler said: "We had a great time learning and hearing the stories of Key West! Ted was great and very knowledgeable!"


Key West Ghosts and Gravestones Trolley Tour

Key West Ghosts and Gravestones Trolley Tour

star-4
278
  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$38.80
From
$38.80
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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* A traveler said: "It was so much intriguing information at once. So fun in one hour. Our tour guide was amazing. She took us through the haunted maritime museum and honored the African Americans that were refugees in Key West. So patient with all of our questions"


Key West Historic District Small-Group Walking Tour

Key West Historic District Small-Group Walking Tour

star-5
28
  • 2 hours
  • Free Cancellation
From
$46.99
From
$46.99
You will be amazed by how much history and culture our small island has! Local Guide will take you on a time travel adventure. As you stroll through the scenic streets of the Old Town, you will learn how the island was discovered and became one of the richest cities in the USA! Hear the stories of the first industries on the island, such as shipwrecking, sponge harvesting and cigarmaking. Also, learn what key role Key West played in the Cuban fight for its independence and find out why Key West declared the war against the United States. What to bring and to wear: Comfortable clothing and shoes, sunscreen, hat, sunglasses, water.
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* A traveler said: "We had a wonderful time. Our guide was very knowledgeable and professional. The in-depth history of the island and architectural descriptions were excellent."


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

Key West Craft Cocktail Crawl

star-5
127
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$88.68
From
$88.68
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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* A traveler said: "The Tiki Hut and the volcano. Enjoyed hearing about the history of the island. The brewery was very interesting and the beer was good.."


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
1101
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$89.95
From
$89.95
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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* A traveler said: "Beautiful sunset ! Friendly snd helpful staff. Comfortable boat , limited people. Kirk even helped raise the sail."


Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
521
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$50.35
From
$50.35
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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* A traveler said: "The knowledge of the drivers excellent! Very enjoyable . Great way to see all sights then decide Done"


Key West Florida Reef Half-Day Snorkeling Excursion

Key West Florida Reef Half-Day Snorkeling Excursion

star-4.5
674
  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$45.95
From
$45.95
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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* A traveler said: "Poor water clarity due to weather but overall a fun day on the water. Definitely puts you in vacation mode."


Key West Pub Crawl

Key West Pub Crawl

star-4.5
152
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.99
From
$34.99
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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* A traveler said: "Great Tour Guide -Julie Very organized and great people wanting to have fun. Would highly recommend to get to get the feel of Key West. Drinks were fantastic !"


Southernmost Key West History and Culture Small-Group Walking Tour

Southernmost Key West History and Culture Small-Group Walking Tour

star-5
49
  • 1 hour 45 minutes
  • Free Cancellation
From
$39.99
From
$39.99
Join us for a 1.5-hour adventure! Our tour is led by knowledgeable local guides. As we walk through the streets of Key West’s old town, you will discover the history and culture of our island. Shipwrecking, sponging, cigar manufacturing, treasure hunting - it’s all about Key West! What to bring: Hat, sunglasses, and sunblock is a must. Bring at least one bottle of water for yourself. Wear comfortable clothing and shoes. Sneakers are the best option. Camera or your phone to take pictures. Your adventurous spirit :)
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* A traveler said: "Alejandro was very knowledgeable and friendly. Both my son and I appreciated seeing scanned old photos and documents describing the unique history of Key West."


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

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

star-5
48
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
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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* A traveler said: "What a wealth of knowledge Richard has about Key West! His tour is excellent and all the homes we saw were new to us. He does not disappoint! This is a great tour to take at the beginning of your stay so you can learn as much as possible and enjoy Key West to the fullest."


Easy Stroll Through Downtown Key West Audio Tour

Easy Stroll Through Downtown Key West Audio Tour

star-4.5
3
  • 1 hour
  • Taking safety measures
From
$10.99
From
$10.99
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 1 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. Within 24 hours of purchasing (usually sooner,) you'll receive an email with a login address and coupon code allowing you to access your tour.
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* A traveler said: "Enjoyed the commentaries for various sites, such as Hemingway. Great overview after our arrival. Maps included really helpful."


PRIVATE Welcome to Key West Walking Tour
Likely to Sell OutLikely to Sell Out

PRIVATE Welcome to Key West Walking Tour

star-5
8
  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
  • Taking safety measures
From
$137.50
Price varies by group size
From
$137.50
Price varies by group size
Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is a private tour just for your group = we won't group you with others. Perfect for your wedding party, couples, family & friends, bachelor and bachelorette party, birthday party, reunion, corporate groups, and more! It's even fun for solo travelers! **If it's too far or too hot to walk, you have the option of hopping on the Duval Loop bus with your guide** It's air-conditioned with several convenient stops throughout Old Town. These tours are private so you can ask questions and we can customize the tour to your interests. Your tour guide is knowledgeable about everything Key West, so don't hesitate to let us know what interests you and what you want to know about Key West. Total distance about 1 1/2 miles.
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* A traveler said: "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."


6th Sense Haunted Tour of Key West

6th Sense Haunted Tour of Key West

star-4
6
  • 2 hours
  • Taking safety measures
From
$26.05
From
$26.05
Brave the haunted city of Key West with our gifted guides. Use paranormal investigation equipment to speak with the spirits that roam the island. Hone your 6th sense and connect with the ghosts that linger in the most beautiful and historic areas of the city. Are you brave enough to join us?
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* A traveler said: "Great tour guide and story teller. Came back to the hotel and I think my entire family was comparing stories."


The Dark Side of Key West Ghost Tour

The Dark Side of Key West Ghost Tour

star-4.5
71
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$34.99
From
$34.99
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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* A traveler said: "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!"


Old Town Key West Literary Walking Tour
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Old Town Key West Literary Walking Tour

star-5
55
  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00
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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* A traveler said: "Sarah was terrific! This is the third time I have done this tour and she managed to keep it fresh and entertaining."


Highlights and Stories of Key West - Small Group Walking Tour

Highlights and Stories of Key West - Small Group Walking Tour

star-5
42
  • 2 hours 15 minutes
  • Free Cancellation
  • Taking safety measures
From
$45.00
From
$45.00
Key West Highlights and Stories- “2020 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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Go Miami All-Inclusive Pass with Hop-on Hop-off and Zoo Miami
The Go Miamiℱ Pass is an all-inclusive pass offering the best choice for maximum savings and flexibility when visiting Miami and South Beach. Choose 1-, 2-, 3-, or 5-day passes and save up to 55 percent versus paying at the gate—like a trip to the Key West Day Trip or an Everglades airboat ride, just to name a few. Each pass is good for two weeks from first use. Access on your mobile device or print and go. It’s that simple to experience some of Miami’s best attractions. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 30 days and/or the remaining number of attraction choices purchased.
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* A traveler said: "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!"


The Ghosts of Key West Walking Tour

The Ghosts of Key West Walking Tour

star-4.5
37
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$24.99
From
$24.99
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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* A traveler said: "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!"


ConchTales and Dreams: Food, Drink and Fun Tour of Key West
Likely to Sell OutLikely to Sell Out

ConchTales and Dreams: Food, Drink and Fun Tour of Key West

star-4.5
45
  • 3 hours
  • Free Cancellation
From
$93.75
From
$93.75
Get to know the sights, sounds and tastes of Key West on this guided, 3-hour, small-group tour. Enjoy three drinks and three food tastings at some of the best pubs, dives and diners in Old Town and the Historic Seaport at Key West Bight Marina. Also, visit the Key West Legal Rum Distillery for a tour and tasting. Along the way, learn about the rich history and traditions of this island city, whose visitors have included fortune hunters, wreckers, spongers, pirates, tobacconists, artists, poets and writers.
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* A traveler said: "Very, very good tour, excellent tour guide, overall a highly recommended tour!"


Beach Day in Key West with Picnic Lunch

Beach Day in Key West with Picnic Lunch

star-5
29
  • 3 to 5 hours
  • Free Cancellation
From
$125.00
From
$125.00
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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* A traveler said: "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!!"


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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?
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What Walking Tours in Key West are taking additional safety precautions?
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What Walking Tours in Key West are good for avoiding crowds?