Top Key West Historical & Heritage Tours

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Key West Historical & Heritage Tours are: Hemingway's Key West Self Guided outdoor Walking Audio Tour Hemingway Food and Walking Tour Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader Ghosts of Key West: Haunted History Walking Tour Key Lime Pie Walking Tour of Key West Historic Seaport

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

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best kid-friendly Key West Historical & Heritage Tours are: Key West Conch Tour Train Jimmy Buffett Tour Harry S Truman Little White House Admission Key West Historic Bahama Village & Hemingway Heritage Key West Shipwreck Treasure Museum Admission View all kid-friendly Tours →

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

Key West Historical & Heritage Tours with Instant Confirmation include: Key West Conch Tour Train Guided Bike Tour of Old Town Key West Jimmy Buffett Tour Harry S Truman Little White House Admission Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours) View all Tours with Instant Confirmation →

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

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: Key West Conch Tour Train Guided Bike Tour of Old Town Key West Jimmy Buffett Tour Harry S Truman Little White House Admission Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours) View all Tours with Free Cancellation →

Q: I need a ride! Which Key West Historical & Heritage Tours have Hotel Pickup?

No problem. These Key West Historical & Heritage Tours include Hotel Pickup: Full-Day Tour of Florida Keys Including Aquarium Encounters from Key West View all Tours with Hotel Pickup →

Q: Got any more Key West trip ideas?

We sure do. Check out our curated lists of hand-picked Key West Tours. Top 10 Key West 2026 Senior-friendly tours Key West The best tours and activities for culture lovers in Key West Top Day Trips from Key West Things to do in Key West this summer View all Key West Trip Ideas →

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

Based on our sales data over the past year, the most popular styles of tours and activities in Key West are: Key West Kid Friendly Key West Kid Friendly Tours & Activities Key West Vehicle Rentals Key West Golf Cart Rentals Key West Water Sports View all tour styles in Key West →

Hemingway's Key West Self Guided outdoor Walking Audio Tour

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to? …More

4.3 (3)

Hemingway's Key West Self Guided outdoor Walking Audio Tour

Want to discover Hemingway's story in Key West? This tour is outside (no tickets to the Hemingway house) See the many sites he's linked to?...

60 to 90 minutes Free Cancellation

4.3 (3)

from
$8

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, …More

4.8 (109)

Hemingway Food and Walking Tour

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,...

2 hours Free Cancellation

4.8 (109)

from
$99

Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader

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 …More

4.7 (7)

Key West Smartphone guided Ghost Walking Tour App/GPS/EMF Reader

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...

40 to 55 minutes Free Cancellation

4.7 (7)

from
$10

Ghosts of Key West: Haunted History Walking Tour

Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost …More

4.6 (130)

Ghosts of Key West: Haunted History Walking Tour

Discover a darker side of Key West on a 90-minute walking ghost tour through the historic streets of Old Town. Led by an engaging Ghost...

1 hour 30 minutes Free Cancellation

4.6 (130)

from
$30

Key Lime Pie Walking Tour of Key West Historic Seaport

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie, …More

4.9 (62)

Key Lime Pie Walking Tour of Key West Historic Seaport

Taste the sweetest adventure in Key West—sunshine, stories, and the island’s most iconic dessert. Led by a Key West expert who’s part historian, part foodie,...

1 hour 30 minutes Free Cancellation

4.9 (62)

from
$70

Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs

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 …More

5.0 (69)

Key West Conch Republic Tiki Pedicab Experience by Kokomo Cabs

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...

2 hours 30 minutes Free Cancellation

5.0 (69)

from
$158

Key West Attractions Pass with Trolley Tour

Explore the vibrant sights of Key West with the Old Town Trolley, Aquarium, and Shipwreck Museum package. This tour offers unlimited hop-on, hop-off access to …More

3.0 (1)

Key West Attractions Pass with Trolley Tour

Explore the vibrant sights of Key West with the Old Town Trolley, Aquarium, and Shipwreck Museum package. This tour offers unlimited hop-on, hop-off access to...

1 hour 30 minutes Free Cancellation

3.0 (1)

from
$93

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

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 …More

4.9 (37)

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

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...

7 hours Hotel pickup offered Free Cancellation

4.9 (37)

from
$100

PRIVATE Welcome to Key West Walking Tour

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 …More

4.9 (22)

PRIVATE Welcome to Key West Walking Tour

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...

90 to 180 minutes Free Cancellation

4.9 (22)

from
$55

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

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 …More

4.3 (30)

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

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...

90 to 120 minutes Free Cancellation

4.3 (30)

from
$15

Key West Ghost Tours: Southernmost Shadows and Ghosts

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate …More

4.6 (30)

Key West Ghost Tours: Southernmost Shadows and Ghosts

Explore the eerie streets of Key West with Southernmost Ghosts on a captivating hour-long walking tour that uncovers the city’s dark past. Led by passionate...

1 hour Free Cancellation

4.6 (30)

from
$32

Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else …More

5.0 (1)

Key West UFO Skywatch Tour with Night Vision

Search the skies over Key West for UFOs using powerful third-generation night-vision technology. Join Captain Heather for a 75-minute oceanfront UFO skywatch unlike anything else...

1 hour 15 minutes Free Cancellation

5.0 (1)

from
$49

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). …More

4.7 (13)

Hemingway Tour

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)....

1 hour 5 minutes Free Cancellation

4.7 (13)

from
$69

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the …More

5.0 (13)

The Keys at Golden Hour Ultimate Private Sunset Tiki Cruise

Drift into tranquility on this private 2-Hour Sunset Tiki Cruise and witness the stunning sunset over the Florida Keys. Glide across crystal-blue waters as the...

2 hours Free Cancellation

5.0 (13)

from
$599

Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll …More

5.0 (7)

Key West After Dark, Ghost, Santeria & Voodoo Pedicab Tour

Embark on an eerie adventure through Key West's Old Town in a cozy pedicab, where the island's haunted past comes to life. As we roll...

1 hour 30 minutes Free Cancellation

5.0 (7)

from
$158

History Nature and Culture of Key West Walking Tour

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local …More

5.0 (3)

History Nature and Culture of Key West Walking Tour

This tour goes beyond the typical Key West history walk by connecting the island's people, cultures, architecture, plants & wildlife. Led by a passionate local...

1 hour 30 minutes Free Cancellation

5.0 (3)

from
$69

Key West Odyssey: Uncover Island Secrets, Walk by Locals

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic …More

5.0 (2)

Key West Odyssey: Uncover Island Secrets, Walk by Locals

Join us for an immersive walking tour of the Key West Historic District, where each step reveals captivating stories and hidden gems. We’ll explore iconic...

1 hour 30 minutes Free Cancellation

5.0 (2)

from
$60

America's Most Haunted Firehouse Ghost Hunt in Key West

Go where other tours can’t. Step inside Key West’s historic firehouse after dark for a two-hour paranormal experience combining immersive history with hands-on investigation. Begin …More

4.6 (11)

America's Most Haunted Firehouse Ghost Hunt in Key West

Go where other tours can’t. Step inside Key West’s historic firehouse after dark for a two-hour paranormal experience combining immersive history with hands-on investigation. Begin...

2 hours Free Cancellation

4.6 (11)

from
$95

Explore the vibrant history of Key West on this engaging bike tour. Pedal through charming streets as you uncover the stories behind the island's notable …More

5.0 (1)

Historic Key West Bike Tour

Explore the vibrant history of Key West on this engaging bike tour. Pedal through charming streets as you uncover the stories behind the island's notable...

2 hours Free Cancellation

5.0 (1)

from
$79