Recent Searches
Clear

Top Key West Cultural Tours

Saved to wishlist!
Dates
Select Dates
Half-day Tours
Half-day Tours
Historical Tours
Historical Tours
Pedicab Tours
Pedicab Tours
E-Bike Tours
E-Bike Tours
Walking Tours
Walking Tours
Private and Luxury
Private and Luxury
Adventure Tours
Culinary & Gourmet Tour
Culinary & Gourmet Tour
Rail Tours
Rail Tours
Private Sightseeing Tours
Private Sightseeing Tours
Food Tours
Food Tours
Literary Tours
Sightseeing Tours
Sightseeing Tours
Bike Tours
Bike Tours
Audio Guides
Audio Guides
Ghost & Vampire Tours
Ghost & Vampire Tours
Street Food Tours
Street Food Tours
Beer & Brewery Tours
Beer & Brewery Tours
Pub Tours
Pub Tours
Car Tours
Car Tours
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in Key West. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

27 results | All Key West Tours

Sort by: Featured

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
540
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.
More
  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Guided Bicycle Tour of Old Town Key West

Guided Bicycle Tour of Old Town Key West

star-5
1234
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.
More
  • 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
808
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$32.26
From
$32.26

Key West Historic District Small-Group Walking Tour

Special Offer

Key West Historic District Small-Group Walking Tour

star-5
30
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.
More
  • 2 hours
  • Free Cancellation
From
$42.29
$46.99
$4.70 savings
From
$42.29
$46.99
$4.70 savings

Key West Ghosts and Gravestones Trolley Tour

Key West Ghosts and Gravestones Trolley Tour

star-4
301
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.
More
  • 1 hour
  • Free Cancellation
From
$38.80
From
$38.80

Key West Pub Crawl

Key West Pub Crawl

star-4.5
161
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.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
$34.99
From
$34.99

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
254
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.
More
  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

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
1132
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.
More
  • 2 hours
  • Free Cancellation
From
$89.95
From
$89.95

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

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

star-5
52
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.
More
  • 2 hours
  • Free Cancellation
From
$45.00
From
$45.00

Key West Hop-On Hop-Off Trolley Tour

Key West Hop-On Hop-Off Trolley Tour

star-4.5
533
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$50.35
From
$50.35

Shark and Wildlife Viewing Adventure in Key West
Likely to Sell OutLikely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

star-5
767
Get up close with sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast of Key West. See dolphins, stingrays, turtles and birds and learn about Key West’s waters, and then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat. Bring a camera to capture the excitement as these super predators swarm. Cold drinks, snacks and polarized sunglasses are included on this Key West shark cruise.
More
  • 2 hours
  • Free Cancellation
From
$84.27
From
$84.27

Key West Full-Day Power Adventure: Sailing & Watersports Package

Key West Full-Day Power Adventure: Sailing & Watersports Package

star-4.5
592
Enjoy the Key West sunshine on a full-day catamaran excursion, and take part in a range of watersports, too. As you cruise around the alluring Gulf of Mexico, gaze out at the scenery and spot local marine life. Choose from a range of activities from snorkeling and kayaking to adrenaline-fuelled parasailing or Jet Skiing. Breakfast and lunch are served on board.
More
  • 6 hours
  • Free Cancellation
From
$209.95
From
$209.95

Key West Conch Tour Train

Key West Conch Tour Train

star-4
202
Explore the best that Key West has to offer on this narrated, Conch Train Tour. See Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original, and most iconic, sightseeing tour.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$39.85
From
$39.85

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

Key West Craft Cocktail Crawl

star-5
138
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.
More
  • 3 hours
  • Free Cancellation
From
$88.68
From
$88.68

Old Town Key West Literary Walking Tour

Old Town Key West Literary Walking Tour

star-5
55
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.
More
  • 1 hour 30 minutes
  • Free Cancellation
From
$30.00
From
$30.00

Southernmost Key West History and Culture Small-Group Walking Tour

Special Offer

Southernmost Key West History and Culture Small-Group Walking Tour

star-5
51
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.
More
  • 1 hour 45 minutes
  • Free Cancellation
From
$35.99
$39.99
$4.00 savings
From
$35.99
$39.99
$4.00 savings

Highlights and Stories of Key West - Small Group Walking Tour

Highlights and Stories of Key West - Small Group Walking Tour

star-5
42
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.
More
  • 2 hours 15 minutes
  • Free Cancellation
From
$45.00
From
$45.00

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
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.
More
  • 3 hours
  • Free Cancellation
From
$93.75
From
$93.75

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West

star-5
17
Swap crowded bus tours for a private and personalized tour of Key West on a comfortable, and unique, tiki bike. Your driver will pedal you around the streets of Old Town and the Historic District to top attractions and places that cannot be reached by bus. You'll also be treated to a slice of famous Kermit's Key lime pie.
More
  • 2 hours 30 minutes
  • Free Cancellation
From
$224.99
per group
From
$224.99
per group

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

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.
More
  • 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

Private Highlights and Stories of Key West Walking Tour

Private Highlights and Stories of Key West Walking Tour

star-5
5
Swap the standard sightseeing tours of Key West for a more personalized experience. This private tour is exclusively for your group and led by a Key West local and unofficial "mayor." As you stroll through the Old Town streets, you'll learn all about the colorful histories and personalities that have shaped Key West.
More
  • 2 hours 15 minutes
  • Free Cancellation
From
$79.00
Price varies by group size
From
$79.00
Price varies by group size

Private Key West Historic Homes and Island History Walking Tour

Private Key West Historic Homes and Island History Walking Tour

star-5
5
Historic Homes & Stories of Key West- 2020 and 2021 WINNER- "Best Key West History Tour" Join our award-winning guides for a wonderful, fun, and informative 2 hour stroll through the celebrated Old Town neighborhoods where you'll discover many of the most beautiful, historic homes and unique architectural landmarks that have contributed so significantly to the history, culture, and legends of our remarkable island community. We’ll see the exteriors of a variety of beautiful homes and public buildings, each with its own legendary story, notable history, and rich style. There's something for everyone to enjoy on this fascinating look behind the scenes of historic Key West. *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 the history of Old Town Key West with you.
More
  • 2 hours
  • Free Cancellation
From
$79.00
Price varies by group size
From
$79.00
Price varies by group size

Cruise Through Key West's Black History Audio Tour

Cruise Through Key West's Black History Audio Tour

star-4.5
3
Turn your phone or tablet into a local tour guide! Download this location-aware audio/media tour, then cruise! Nowhere on this tour will the speed limit exceed 35 mph. PLEASE NOTE ELECTRIC CAR, SCOOTER OR BIKE RENTAL IS NOT INCLUDED. Rent from one of the vendors recommended at the beginning of the tour, then sight-see from the comfort of your own car, scooter or bike. Learn about Key West's deep ties to the Bahamas and the city's pivotal role defeating the Confederacy. Discover why 250 Africans are buried by the beach, and the surprising tourist spot that was once the island's "blacks only" beach. Visit the island's first black church. Find the Keys' best conch salad, get a taste of Haitian and Cuban flavors and sample Key Lime pie. Historic photos plus links to restaurant menus and websites rest at your fingertips. Spend one hour or a whole day. Shortly after booking, you'll receive a confirmation email with login instructions and a coupon code.
More
  • 1 to 4 hours
From
$9.99
From
$9.99

Easy Stroll Through Downtown Key West Audio Tour

Special Offer

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.
More
  • 1 hour
From
$8.49
$9.99
$1.50 savings
From
$8.49
$9.99
$1.50 savings

Filters

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 Cultural Tours in Key West?
Q:
What Cultural Tours in Key West are taking additional safety precautions?
Q:
What Cultural Tours in Key West are good for avoiding crowds?