Top Key West Historical & Heritage Tours

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  • 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

    307

    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
    $39.98
    Details
    from
    $39.98
    Details
  • Key West Historic District Small-Group 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 District Small-Group Walking Tour

    126

    Experience Historic Key West With A Small-Group Walking TourEver wondered how the island of Key West was discovered and became so rich? Explore Key West’s...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $46.99
    Details
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    $46.99
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  • Guided Bicycle Tour of Old Town Key West
    Likely to Sell Out
    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

    617

    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
    $54
    Details
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    $54
    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

    42

    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
  • 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

    35

    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
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    $79
    Details
  • Key West Shore Excursion: Conch Tour Train

    Key West Shore Excursion: Conch Tour Train

    13

    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
    $39.86
    Details
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    $39.86
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  • Southernmost Key West History and Culture Small-Group Walking Tour
    Likely to Sell Out

    Southernmost Key West History and Culture Small-Group Walking Tour

    29

    Meet The Locals, On Foot, At Eye LevelIf you’re like us, you think of travel as more than just “going places.” You crave experience and...
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     1 hour 45 minutes  Free Cancellation  Instant Confirmation
    from
    $39.99
    Details
    from
    $39.99
    Details
  • Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West

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

    12

    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
    $165
    Details
    from
    $165
    Details
  • Hemingway Food and Walking Tour
    Likely to Sell Out
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Hemingway Food and Walking Tour

    56

    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,...
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     2 hours  Free Cancellation  Instant Confirmation
    from
    $99
    Details
    from
    $99
    Details
  • PRIVATE Key West Haunted History Walking Tour
    Likely to Sell Out

    PRIVATE Key West Haunted History Walking Tour

    8

    Walk through Old Town Key West with a long-time local, hear the haunted history of Key West, her beautiful historic mansions, and visit a haunted...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
    from
    $137.50
    Details
    from
    $137.50
    Details
  • The Ghosts of Key West Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    The Ghosts of Key West Walking Tour

    78

    The Ghosts of Key West Tour is our family friendly option and is very rich in Key West’s history, hauntings and ghost stories. On this...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $24.99
    Details
    from
    $24.99
    Details
  • Hemingway Tour

    Hemingway Tour

    6

    You will begin this 65 minute nighttime guided walking tour by meeting your tour guide at Capt. Tony's Saloon outside front doors (428 Greene Street)....
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     1 hour 5 minutes  Free Cancellation  Instant Confirmation
    from
    $69
    Details
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    $69
    Details
  • PRIVATE Welcome to Key West Walking Tour
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    PRIVATE Welcome to Key West Walking Tour

    4

    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...
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     90 to 120 minutes  Free Cancellation  Instant Confirmation
    from
    $137.50
    Details
    from
    $137.50
    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

    37

    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
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  • Key West Haunted Pub Crawl Walking Tour
    Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Haunted Pub Crawl Walking Tour

    31

    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
  • Old Town Key West Literary Walking Tour

    Old Town Key West Literary Walking Tour

    34

    Join us every weekend for the Old Town Literary Walking Tour, a stroll through downtown Key West, illuminating stories of writers that have called our island...
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     1 hour 30 minutes  Free Cancellation  Instant Confirmation
    from
    $30
    Details
    from
    $30
    Details
  • Key West’s Old Town Treasures: A Self-Guided Audio Tour

    Key West’s Old Town Treasures: A Self-Guided Audio Tour

    5

    See Key West’s top attractions from the Lighthouse to the Little White House at your own pace with this affordable walking tour.• Find out how...
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     90 to 120 minutes  Instant Confirmation
    from
    $6.99
    Details
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    $6.99
    Details
  • Key West's Self Guided Ghost Walking Tours Smartphone Navigated on WalknTours

    Key West's Self Guided Ghost Walking Tours Smartphone Navigated on WalknTours

    3

    Go at your own pace and schedule. You'll see Key West's most haunted spots and hear their ghostly stories on spooky solo walking tour on...
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     40 to 55 minutes  Free Cancellation  Instant Confirmation
    from
    $6.50
    Details
    from
    $6.50
    Details
  • Cruise Through Key West's Black History Audio Tour

    Cruise Through Key West's Black History Audio Tour

    5

    Turn your phone or tablet into a local tour guide! Download this location-aware audio/media tour, then cruise. PLEASE NOTE ELECTRIC CAR, SCOOTER OR BIKE RENTAL...
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     1 to 4 hours  Instant Confirmation
    from
    $10.99
    Details
    from
    $10.99
    Details
  • Bahama Village Walking Tour

    Bahama Village Walking Tour

    Tours will begin at the corridor of the Southernmost District near the Key West Lighthouse and the home of the infamous author Ernest Hemingway. We...
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     1 to 2 hours  Free Cancellation  Instant Confirmation
    from
    $30
    Details
    from
    $30
    Details
  • Key West Historic Homes and Island History - Small Group Walking Tour

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

    237

    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
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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 Historical & Heritage Tours?

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

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

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

View all kid-friendly Tours →

Q: Which Key West Historical & Heritage Tours have Instant Confirmation?

A: Key West Historical & Heritage Tours with Instant Confirmation include:

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Q: Which Key West Historical & Heritage Tours have Free Cancellation?

A: Key West Historical & Heritage 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 Historical & Heritage Tours include Hotel Pickup?

A: No problem. These Key West Historical & Heritage Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

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 →