Top Key West Cultural & Theme Tours

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  • Key West Ghosts and Gravestones Trolley Tour

    Key West Ghosts and Gravestones Trolley Tour

    775

    Join your gravedigger guide aboard the Trolley of the Doomed for a journey through Key West's darker side! Take an evening trolley ride down the...
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     1 hour  Free Cancellation
    from
    $39.85
    Details
    from
    $39.85
    Details
  • Key West Craft Cocktail Crawl
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Craft Cocktail Crawl

    361

    Join us on a sip and stroll through Key West's craftiest bars and hidden local gems enjoying 5 local cocktails & 2 food tastings! Discover the...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $93.68
    Details
    from
    $93.68
    Details
  • Key West Conch Tour Train
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Conch Tour Train

    488

    Experience the best of Key West on the famous Conch Tour Train! One of Florida’s most popular attractions, the Conch Tour Train has been entertaining...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $45.10
    Details
    from
    $45.10
    Details
  • Key West Ghost and Mysteries Guided Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Ghost and Mysteries Guided Tour

    944

    Discover why Key West is one of the most haunted locations in the country on this 90 minute walking tour that starts at the corner...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $32.26
    Details
    from
    $32.26
    Details
  • Robert the Doll Experience VIP Ghost Tour at Fort East Martello
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Robert the Doll Experience VIP Ghost Tour at Fort East Martello

    78

    This is the only ghost tour in Key West where you will meet the infamous Robert the Doll. While other ghost tours stop outside of...
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     1 hour  Free Cancellation  Instant Confirmation
    from
    $45
    Details
    from
    $45
    Details
  • Key West Historic District Small-Group Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Historic District Small-Group Walking Tour

    153

    Experience Historic Key West With A Small-Group Walking Tour Ever wondered how the island of Key West was discovered and became so rich? Explore Key...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $46.99
    Details
    from
    $46.99
    Details
  • The Original Key West Ghost Hunt
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    The Original Key West Ghost Hunt

    63

    We are the only locally owned haunted attraction with exclusive access to two locations. Our local experts provide Ghost Hunting equipment along with personal experience...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $28
    Details
    from
    $28
    Details
  • Guided Bicycle Tour of Old Town Key West
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Guided Bicycle Tour of Old Town Key West

    1866

    Ride with us for a truly unique and unforgettable Key West experience! See the islands top attractions with your own local guide! Cruise Old Town,...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $49
    Details
    from
    $49
    Details
  • Key West Historic Seaport Food Tasting and Cultural Walking Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Historic Seaport Food Tasting and Cultural Walking Tour

    442

    Discover the flavors of the ocean on this locally guided 3-hour food tour of Key West. Savor maritime history through delicious seafood (or tasty non-seafood...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $93.41
    Details
    from
    $93.41
    Details
  • Key West Southernmost Food and Cultural Walking Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Southernmost Food and Cultural Walking Tour

    1037

    Enjoy a taste of Key West on this 3-hour food walking tour, led by an expert guide. Along the way visit 5 locally-run “mom and pop” establishments in...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $93.41
    Details
    from
    $93.41
    Details
  • The Dark Side of Key West Ghost Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    The Dark Side of Key West Ghost Tour

    242

    The Dark Side of Key West is our adult’s only option that focuses on Key West’s dark and salacious past. We will discuss pirates, Count...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $34.99
    Details
    from
    $34.99
    Details
  • Jimmy Buffett Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Jimmy Buffett Tour

    46

    You will begin this 1 hour and 30 minute guided tour by meeting your tour guide, (who will be wearing a neon green shirt) at...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $79
    Details
    from
    $79
    Details
  • Southernmost Key West History and Culture Small-Group Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Southernmost Key West History and Culture Small-Group Walking Tour

    72

    Meet The Locals, On Foot, At Eye Level If you’re like us, you think of travel as more than just “going places.” You crave experience...
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     1 hour 45 minutes  Free Cancellation  Instant Confirmation
    from
    $39.99
    Details
    from
    $39.99
    Details
  • Key West Shore Excursion: Conch Tour Train
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Shore Excursion: Conch Tour Train

    14

    Ride the World Famous Conch Tour Train, the charming and whimsical Key West attraction that has been delighting locals and visitors alike since 1958....
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $45.10
    Details
    from
    $45.10
    Details
  • Key West Haunted Pub Crawl Walking Tour

    Key West Haunted Pub Crawl Walking Tour

    44

    Our Key West Haunted Pub Crawl showcases some of the more unusual and lesser-known histories of Key West. From the island's demonic dolls to one...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $29.99
    Details
    from
    $29.99
    Details
  • Private Key West Conch Republic Tiki Bike Experience by Kokomo Cabs Key West
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

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

    48

    You will sit and relax on our spacious and comfortable tiki bike as your private guide/driver takes you on a pleasant ride around the enchanting...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    from
    $224.99
    Details
    from
    $224.99
    Details
  • Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

    17

    Depart the island of Key West & enjoy a full day of sightseeing along the iconic Overseas Highway! You'll travel halfway up the keys to...
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     7 hours  Hotel pickup offered  Free Cancellation  Instant Confirmation
    from
    $155
    Details
    from
    $155
    Details
  • Private Highlights and Stories of Key West Walking Tour
    Likely to Sell Out

    Private Highlights and Stories of Key West Walking Tour

    7

    Key West Highlights and Stories Private Tour- “2020 and 2021 WINNER "Best Key West Walking Tour" Join our award-winning guides for a wonderful, fun, and...
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     2 hours 30 minutes  Free Cancellation
    from
    $189
    Details
    from
    $189
    Details
  • Key West Sunset Bite, Sip & Stroll Audio Tour
    Likely to Sell Out

    Key West Sunset Bite, Sip & Stroll Audio Tour

    1

    Turn your phone or tablet into a local tour guide! This location-aware audio/multimedia tour lets you enjoy historic photos, recordings and videos plus links to...
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     35 to 120 minutes  Instant Confirmation
    from
    $9.99
    Details
    from
    $9.99
    Details
  • Key West Historic Homes and Island History - Small Group Walking Tour
    Likely to Sell Out

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

    270

    Historic Homes & Island History of Key West- 2020, 2021, and 2022 WINNER- "Best Key West History Tour" Cool Destinations ranked top 10 history tours in...
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     2 hours 15 minutes  Free Cancellation
    from
    $49
    Details
    from
    $49
    Details
  • Sunset Sail on Historic Schooner in Key West
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Sunset Sail on Historic Schooner in Key West

    68

    Set sail for a beautiful Key West sunset on the historic schooner When And If! Commissioned by then Colonel George Patton "When the war is...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $99
    Details
    from
    $99
    Details
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Frequently Asked Questions

The answers provided below are based on answers previously given to customers' questions.

Q: What are the best options for Key West Cultural & Theme Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best Key West Cultural & Theme Tours are:

Q: What are the best kid-friendly options for Key West Cultural & Theme Tours Tours?

A: According to verified reviews on Cool Destinations and TripAdvisor, the best kid-friendly Key West Cultural & Theme Tours are:

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Q: Which Key West Cultural & Theme Tours have Instant Confirmation?

A: Key West Cultural & Theme Tours with Instant Confirmation include:

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Q: Which Key West Cultural & Theme Tours have Free Cancellation?

A: Key West Cultural & Theme Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

Q: I need a ride! Which Key West Cultural & Theme Tours include Hotel Pickup?

A: No problem. These Key West Cultural & Theme Tours include Hotel Pickup:

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Q: Got any more Key West trip ideas?

A: We sure do. Check out our curated lists of hand-picked Key West Tours.

View all Key West Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Key West?

A: Based on our sales data over the past year, the most popular styles of tours and activities in Key West are:

View all tour styles in Key West →