Top Key West Cultural & Theme Tours

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

Key West Cultural & Theme Tours with Instant Confirmation include: Guided Bike Tour of Old Town Key West Southernmost Food & Cultural Walking Tour by Key West Food Tours Key West Historic Seaport Food & Walking Tour Key West Craft Cocktail Crawl Jimmy Buffett Tour View all Tours with Instant Confirmation →

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

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: Guided Bike Tour of Old Town Key West Southernmost Food & Cultural Walking Tour by Key West Food Tours Key West Historic Seaport Food & Walking Tour Key West Craft Cocktail Crawl Jimmy Buffett Tour View all Tours with Free Cancellation →

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

No problem. These Key West Cultural & Theme 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 →

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: Robert the Doll After Dark Ghost Tour (1 Hour)

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most …More

4.9 (7)

Key West: Robert the Doll After Dark Ghost Tour (1 Hour)

Go where other tours can't. Enter historic Fort East Martello after dark for an eerie encounter with Robert the Doll, one of Key West's most...

1 hour Free Cancellation

4.9 (7)

from
$45

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

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our …More

5.0 (5)

Key West Christmas Cruise with Live Band and Drinks

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our...

1 hour 30 minutes Free Cancellation

5.0 (5)

from
$98

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 (4)

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 (4)

from
$69

Half Day Luxury Boat Tour in Key West with Snorkeling

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring …More

5.0 (3)

Half Day Luxury Boat Tour in Key West with Snorkeling

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring...

4 hours Free Cancellation

5.0 (3)

from
$200

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

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

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

Dark Corners of Key West Private Walking Tour

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s …More

5.0 (1)

Dark Corners of Key West Private Walking Tour

Join us on a 2-hour private, exclusive walking tour through the dark and untold stories of Key West. Our tour will begin at St. Paul’s...

2 hours Free Cancellation

5.0 (1)

from
$150

Key West Beach Elopement Intimate Wedding All Inclusive

Our beach elopement package is designed for couples who want a meaningful wedding experience without the stress an expense of planning a large celebration. Our …More

5.0 (1)

Key West Beach Elopement Intimate Wedding All Inclusive

Our beach elopement package is designed for couples who want a meaningful wedding experience without the stress an expense of planning a large celebration. Our...

1 hour Free Cancellation

5.0 (1)

from
$1,350

Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering …More

5.0 (1)

Florida Audio Tour Bundle 3 Self-Guided Sightseeing Tours

Embark on an unforgettable journey through Florida's diverse landscapes with our Florida Self-Guided Audio Tour Bundle! Cruise the iconic Overseas Highway to Key West, uncovering...

4 days Free Cancellation

5.0 (1)

from
$40

Southernmost Key West Historical Tour in Small Group

Travel The Keys is a guided tour and concierge company based in Key West, Florida. We offer unique historical tours in Key West, presented by …More

5.0 (1)

Southernmost Key West Historical Tour in Small Group

Travel The Keys is a guided tour and concierge company based in Key West, Florida. We offer unique historical tours in Key West, presented by...

1 to 90 minutes Free Cancellation

5.0 (1)

from
$30

Key West Ghosts and Gravestones Trolley Tour

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 …More

4.4 (1,408)

Key West Ghosts and Gravestones Trolley Tour

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...

1 hour Free Cancellation

4.4 (1,408)

from
$40

Key West Ghost and Mysteries Guided Tour

This isn’t your average ghost tour. Key West Ghost and Mysteries is a locally owned and operated family business offering a small, intimate experience that …More

4.6 (1,121)

Key West Ghost and Mysteries Guided Tour

This isn’t your average ghost tour. Key West Ghost and Mysteries is a locally owned and operated family business offering a small, intimate experience that...

1 hour 30 minutes Free Cancellation

4.6 (1,121)

from
$35

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 …More

4.5 (881)

Key West Conch Tour Train

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...

1 hour Free Cancellation

4.5 (881)

from
$45

Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt

Unleash your inner ghost hunter! Embark on a spine-tingling 2-hour haunted walking tour through Bone Island's Old Town Key West. You'll first receive your commemorative …More

4.5 (619)

Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt

Unleash your inner ghost hunter! Embark on a spine-tingling 2-hour haunted walking tour through Bone Island's Old Town Key West. You'll first receive your commemorative...

2 hours Free Cancellation

4.5 (619)

from
$32

Harry S Truman Little White House Admission

Tour the historic Harry S. Truman Little White House in Key West and learn about a fascinating period of American history. What was once a …More

4.7 (500)

Harry S Truman Little White House Admission

Tour the historic Harry S. Truman Little White House in Key West and learn about a fascinating period of American history. What was once a...

1 to 2 hours Free Cancellation

4.7 (500)

from
$26

Dare to walk the haunted heart of Key West—where the veil between the living and the dead is razor-thin. Your journey begins sweetly enough at …More

4.7 (350)

Dark Side of Key West Ghost Tour

Dare to walk the haunted heart of Key West—where the veil between the living and the dead is razor-thin. Your journey begins sweetly enough at...

1 hour 30 minutes Free Cancellation

4.7 (350)

from
$35

Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours)

Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside …More

4.7 (169)

Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours)

Go where other tours can’t. Enter historic Fort East Martello after dark, meet Robert the Doll, then stay behind for an extended paranormal investigation inside...

2 hours Free Cancellation

4.7 (169)

from
$99