cool shore excursions®
Top activities
Top landmarks
Trip ideas
Nearby places
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Tours by time
  • Tours by the numbers
  • Top attractions
  • Key West travel guides
  • Key West travel calendar
  • Tours in nearby places
  • Explore Florida tours
Language $Currency
Login / Sign up
Bookings
Bookings
Wallet
$0.00
Wishlists
Wishlists
Cool Rewards Rewards
Gift cards
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates
You booked this experience
You're departing on
Google Calendar
Apple Calendar
Microsoft Outlook
Make your trip unforgettable

Key West Pirate Adventure: Self-Guided Walking Tour

Key West, USA
Book online or call us

from $5 per person

Lowest Price Guarantee
Key West Pirate Adventure: Self-Guided Walking Tour Image 1
Key West Pirate Adventure: Self-Guided Walking Tour Image 2
Key West Pirate Adventure: Self-Guided Walking Tour Image 3
Key West Pirate Adventure: Self-Guided Walking Tour Image 4
Key West Pirate Adventure: Self-Guided Walking Tour Image 5
1 hour 30 minutes (approx.)
Mobile ticket
Offered in: English
Instant confirmation

Overview

Journey through Key West's history on this self-guided adventure featuring swashbuckling pirate legends and maritime mysteries. Your smartphone transforms a regular walk into an epic quest, with historical puzzles, fascinating stories, and clever challenges at every stop.

Each location brings history to life — from ancient landmarks to hidden historical details you'd walk right past without the app. Solve challenges to unlock the next chapter of Key West's story.

This 1–2 hour private adventure runs 24/7. No guide needed — just your smartphone and a sense of curiosity. Available in 5+ languages.

What's Included

  • Built-in GPS-enabled map for easy navigation
  • Mobile access code to the quest
  • Flexibility to start, pause, and resume at your own pace
  • Live tour guide or in-person assistance
See 2 moreSee 1 more

Meeting Location

Meeting point

1 Whitehead Street
Key West, FL 33040, USA

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

428 Greene Street
Key West, FL 33040, USA

What To Expect

Book Online

Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
Read more

Safe & secure Easy breezy Hassle‑free

Key West Shipwreck Museum

Step into the daring world of 19th-century wreckers at the Key West Shipwreck Museum—a treasure trove of maritime history and daring rescues. This unique museum brings to life the island’s golden age of salvaging sunken ships from nearby reefs. As part of your quest, you'll follow cryptic clues through Key West’s streets to find this hidden gem. Once there, solve a clever puzzle tied to its storied past, unlock a forgotten tale of lost treasure, and set off toward your next adventure. Ready to dive into history?
Read more

10 minutes Admission Ticket Free

Mel Fisher Maritime Museum (pass by)

Dive into the thrilling world of deep-sea treasure hunting at the Mel Fisher Maritime Museum in Key West, where the legendary salvager Mel Fisher’s discoveries come to life. This captivating museum showcases sunken treasure and maritime artifacts that shaped Florida’s seafaring history. As part of your quest, follow clever clues through the city to unearth this maritime marvel. Upon arrival, crack a riddle tied to a famed shipwreck, reveal a dramatic narrative from Fisher’s daring dives, and then embark on your next adventure. Ready to unearth some secrets?
Read more

Truman Little White House (pass by)

Step into history at the Harry S. Truman Little White House in Key West, the former presidential retreat where “the Boss” relaxed and made key decisions during his vacations. This charming and stately cottage offers a glimpse into mid‑20th century politics and presidential life. In your quest, you'll follow clever clues through Key West’s historic streets to uncover this iconic site. There, you'll solve a brain‑teasing riddle tied to Truman’s time in office, reveal a hidden anecdote from his stays, then set off on your next adventure. Ready to unlock presidential secrets?
Read more

Truman Waterfront Park (pass by)

Discover the serene charm of Truman Waterfront Park in Key West, where sweeping harbor views, swaying palm trees, and historic naval reminders offer a peaceful escape by the sea. This scenic spot invites travelers to soak in maritime vistas and laid-back island elegance. As part of your quest, follow intriguing clues through town to pinpoint this hidden waterfront haven. Once you arrive, tackle a clever riddle tied to the park’s nautical history, unveil a little-known seafaring tale, and then set course for your next adventure. Ready to unlock its waterfront secrets?
Read more

Rick Worth Mural "Bahama Village Life" (pass by)

Discover the vibrant storytelling of the Rick Worth mural “Bahama Village Life” in Key West, a colorful tribute to the island’s Bahamian heritage, community spirit, and everyday charm. This stunning wall art captures local life with lively scenes of music, seafood, and friendly faces. In this quest, you'll follow intuitive clues winding through Key West’s artistic alleys until you uncover this mural’s hidden home. There, you’ll solve a clever visual riddle inspired by its imagery, unlock an untold tale of Bahama Village’s past, and then continue on to your next exciting destination. Ready to decode its colorful secrets?
Read more

The Hemingway Home and Museum (pass by)

Step into literary legend at Ernest Hemingway’s Spanish Colonial-style home in Key West, where the Nobel Prize-winning author penned classics surrounded by lush gardens and his famously polydactyl cats. This iconic estate immerses travelers in the vibrant life and legacy of one of America’s greatest writers. In your quest, follow intriguing clues through charming streets to uncover this literary landmark. Once there, crack a clever puzzle woven into Hemingway’s world, unveil a little-known anecdote about his island life, and then set off toward your next thrilling discovery. Ready to step into fiction and history?
Read more

Oldest House Museum & Gardens Key West (pass by)

Step into Key West’s past at the Oldest House Museum, a charming 1829 structure that offers a rare glimpse into early island life. This well-preserved home, with live oaks draped overhead and original furnishings inside, transports travelers back two centuries. As part of your quest, follow subtle clues winding through historic streets to discover this hidden gem. There, tackle a clever riddle tied to the home’s earliest inhabitants, unlock a surprising family secret, and then continue on to your next adventure. Ready to unravel history one puzzle at a time?
Read more

Pirates Well (pass by)

Discover the legendary Pirates Well in Key West, a centuries-old spring carved by early settlers—and rumored to have quenched the thirst of seafaring pirates. This rugged stone well nestled in Bahama Village offers a tangible connection to Key West’s swashbuckling past. As part of your quest, you'll follow intriguing clues winding through the neighborhood until you arrive at this historic landmark. There, you’ll solve a clever riddle linked to the well’s pirate lore, unlock a hidden tale of buried treasure, and then set sail for your next adventure. Ready to unearth some salty secrets?
Read more
Show 7 more stops

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller

Frequently Asked Questions (7)

Q: What is the cancellation policy for the Key West Pirate Adventure: Self-Guided Walking Tour?

A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (EST). Read more Apr 2025

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

Still have questions?

We're here to help.
Activity code: C-107194P530

Traveler Photos

Key West Tours
Attractions
Guides
Calendar
View more
View more

Similar Tours & Activities

Key West: Robert the Doll After Dark VIP Ghost Hunt (2 Hours)
Likely to Sell Out
Likely to Sell Out
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
Dark Corners of Key West Private Walking Tour
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 Christmas Cruise with Live Band and Drinks
Likely to Sell Out
Likely to Sell Out
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
Experience Florida Keys Boat Charter Private Tour
5.0 (8)

Experience Florida Keys Boat Charter Private Tour

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while...

1 hour 30 minutes Free Cancellation
5.0 (8)
from
$460
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

Likely to Sell Out
Likely to Sell Out
4.7 (169)

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

4.7 (169)

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
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

5.0 (1)

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 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

Likely to Sell Out
Likely to Sell Out
5.0 (5)

Key West Christmas Cruise with Live Band and Drinks

5.0 (5)

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
Experience Florida Keys Boat Charter Private Tour

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while …More

5.0 (8)

Experience Florida Keys Boat Charter Private Tour

5.0 (8)

Cruise the beautiful waters of the Florida Keys on an authentic tiki bar boat during this 1.5-hour Tiki Fun Cruise. Sip your favorite beverage while...

1 hour 30 minutes Free Cancellation
5.0 (8)
from
$460

Travelers Who Bought This Tour Also Bought

Key West 6 Seater EZGO Golf Cart Rental
Likely to Sell Out
Likely to Sell Out
4.9 (1,436)

Key West 6 Seater EZGO Golf Cart Rental

Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...

3 hours and up Free Cancellation
4.9 (1,436)
from
$180
Key West 4 Seater EZGO Golf Cart Rental
Likely to Sell Out
Likely to Sell Out
4.9 (1,436)

Key West 4 Seater EZGO Golf Cart Rental

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...

3 hours and up Free Cancellation
4.9 (1,436)
$100
$99
Key West 4 Seater Electric Car Rental
Likely to Sell Out
Likely to Sell Out
4.9 (1,168)

Key West 4 Seater Electric Car Rental

Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...

3 hours and up Free Cancellation
4.9 (1,168)
$100
$99
Key West 6 Seater Electric Car Rental
Likely to Sell Out
Likely to Sell Out
4.9 (1,168)

Key West 6 Seater Electric Car Rental

Our 6-seater GEM electric cars beat any regular rental car hands down when it comes to zipping around Key West with a party of 5...

3 hours and up Free Cancellation
4.9 (1,168)
from
$180
Key West 6 Seater EZGO Golf Cart Rental

Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,436)

Key West 6 Seater EZGO Golf Cart Rental

4.9 (1,436)

Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...

3 hours and up Free Cancellation
4.9 (1,436)
from
$180
Key West 4 Seater EZGO Golf Cart Rental

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,436)

Key West 4 Seater EZGO Golf Cart Rental

4.9 (1,436)

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...

3 hours and up Free Cancellation
4.9 (1,436)
$100
$99
Key West 4 Seater Electric Car Rental

Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,168)

Key West 4 Seater Electric Car Rental

4.9 (1,168)

Cruise Key West with family or friends! Four people can get around town in comfort and ease with the smooth, silent GEM 4-seater electric car...

3 hours and up Free Cancellation
4.9 (1,168)
$100
$99
Key West 6 Seater Electric Car Rental

Our 6-seater GEM electric cars beat any regular rental car hands down when it comes to zipping around Key West with a party of 5 …More

Likely to Sell Out
Likely to Sell Out
4.9 (1,168)

Key West 6 Seater Electric Car Rental

4.9 (1,168)

Our 6-seater GEM electric cars beat any regular rental car hands down when it comes to zipping around Key West with a party of 5...

3 hours and up Free Cancellation
4.9 (1,168)
from
$180

Frequently Asked Questions (7)

Activity name

The answers provided below were previously given in response to questions from Cool Shore Excursions customers.

Filter by:

Q: What is the cancellation policy for the Key West Pirate Adventure: Self-Guided Walking Tour?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (EST).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Built-in GPS-enabled map for easy navigation.
  • Mobile access code to the quest.
  • Flexibility to start, pause, and resume at your own pace.
  • 10 location-based puzzle challenges.
  • Rich pirate-themed storyline content.
The following is NOT included:
  • Live tour guide or in-person assistance.
Apr 2025
Q: What is the minimum age for this tour?
A:

The minimum age to participate is 8..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Key West Pirate Adventure: Self-Guided Walking Tour is as follows:

  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Key West Pirate Adventure: Self-Guided Walking Tour will be included in your confirmation email from Cool Shore Excursions. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024
Q: How long does a refund take to reach my card, and can I get it faster?
A:

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

Oct 2026

What's Included

Activity name

  • Built-in GPS-enabled map for easy navigation
  • Mobile access code to the quest
  • Flexibility to start, pause, and resume at your own pace
  • 10 location-based puzzle challenges
  • Rich pirate-themed storyline content
  • Live tour guide or in-person assistance

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller

Report Product Issue

Activity name