Pirates and Treasure: Self Guided Tour of Key West’s Old Town

If you’re a history buff or just someone curious about Key West’s swashbuckling past, this self-guided audio tour offers a fascinating peek into the island’s pirate lore and shipwreck stories. Priced at $29.99 per person, it’s an affordable way to explore at your own pace, with the flexibility to linger or move quickly through the sights. While we haven’t taken this tour ourselves, a lot of travelers find it to be a pretty solid way to get a feel for the Old Town’s legendary past.

Two things we particularly like about this experience are its self-guided nature, which gives you control over your schedule, and the engaging narration led by the character of Captain William Shade—an eccentric pirate ghost who makes the storytelling lively. The tour also covers a wide range of sights, from ghostly bars to historic homes, making it a well-rounded glimpse into Key West’s wild history.

One thing to keep in mind is that this is a walking tour with no included entrance tickets—so if you want to step inside sites like the Oldest House Museum or Mel Fisher’s Maritime Museum, you’ll need to buy those tickets separately. It’s best suited for travelers who enjoy a flexible, independent approach to sightseeing and are comfortable using a smartphone app.

Who this tour suits best:

If you’re comfortable with self-guided audio experiences, love history, and want to explore Key West at your own pace, this tour could be a perfect fit. It’s especially good for those who enjoy stories of pirates, shipwrecks, and the colorful characters that made Key West what it is today.

Key Points

• Flexible self-guided experience allows you to explore at your own pace.
• Historical storytelling led by a pirate ghost makes the tour entertaining.
• Cost-effective at just under $30, but does not include entry to attractions.
• Good for timing—best enjoyed early mornings or before sunset when temperatures are milder.
• Wide range of sites covered, from ghostly bars to historic homes.
• Requires your own device and headphones; no physical guide or transportation included.

Why You Might Love This Experience

This tour is a great way to blend a bit of adventure with history, especially if you like wandering at your own pace. The narration by Captain William Shade adds a fun, spooky element that keeps the storytelling lively, rather than feeling like a typical walking guide. You’ll get a good sense of Key West’s pirate roots and maritime past, all while soaking in the island’s vibe.

What we think makes this stand out is the variety of sites covered. You’ll pass by iconic landmarks like El Meson de Pepe’s, located on the route, which is known for its lively atmosphere (though drinks aren’t included). You also get some historical context about figures like Captain David Porter, who helped transform Key West from a sleepy fishing village into a naval hub.

What to Expect at Each Stop

• El Meson de Pepe’s: Though just a passing point, it’s worth noting for its lively, pirate-era feel—imagine pirates celebrating with rum and salsa (not included but fun to soak in the vibe).
• Key West Historic Memorial Sculpture Garden: Offers insights into how the city developed from humble beginnings into a bustling naval station.
• Capt Tony’s Saloon: Known for its haunted stories and dark past, this bar has ghostly tales and a history of hangings—an ideal eerie stop for those fascinated by haunted locales.
• Oldest House Museum: The oldest structure in Key West, with history tied to wreckers and treasure finders—think of it as a glimpse into the early days of shipwreck salvage.
• Captain George Carey’s House: A historic home that hosted famous figures, adding a touch of cultural depth to the tour.
• Audubon House and Tropical Gardens: Not your typical garden visit, but a window into the untamed, wild side of Key West’s past.
• Mel Fisher’s Maritime Museum: Focused on underwater treasure hunts, perfect for anyone dreaming of sunken ships and buried gold.
• Old Custom House: Once a key point in regulating trade, offering a sense of law and order amid the chaos of pirate tales.
• Final Stop at the Key West Shipwreck Museum: Reflect and soak in the stories of the legendary characters who once roamed these streets.

The Experience in Detail

The beauty of this tour is its flexibility. You can start at the designated meeting point—420 Wall St—and follow the narrated map on your smartphone. The duration varies between about 1 to 1 hour 15 minutes, so you can stretch it out if you want or breeze through if pressed for time.

The narration is lively, with Captain William Shade adding a humorous and spooky touch that makes the stories memorable. The tour is designed to be a sort of ghostly treasure hunt, where each stop uncovers a new piece of Key West’s past.

While the tour doesn’t include entrance fees, it does a good job of contextualizing each site, helping you imagine what life was like for pirates, wreckers, and early settlers. For example, when walking past the Oldest House, you might find yourself picturing wreckers scavenging for gold or rum, turning history into a vivid story.

Reviews from other travelers highlight the tour’s engaging storytelling and the convenience of offline access. One comment praised the “fun pirate voice” and the way it made history come alive, though some mentioned that it’s not a guided tour in the traditional sense—more of an audio experience you can pause and explore.

Since the tour is only available in English, non-English speakers might find it less accessible unless they’re comfortable with the language. Also, as it’s a walking tour, comfortable shoes and sunscreen are a good idea—Key West can get pretty hot, especially in the middle of the day.

The Value for Money

At $29.99, the tour is reasonably priced considering the amount of content and flexibility it offers. You’re paying for the ability to explore at your own pace, along with the engaging narration, which adds a storytelling dimension that you might not get from a regular walking guide. Remember, it doesn’t include entry to attractions, so if you want to go inside specific sites, budget accordingly.

It’s a pretty good deal for those who prefer self-guided experiences over scheduled tours. Plus, with lifetime access to the audio, you can revisit the stories later or share them with travel companions.

Who Should Consider This Tour?

This experience is ideal for independent travelers who enjoy history, stories of pirates and shipwrecks, and prefer exploring without the pressure of a group. It’s also well-suited for early risers or sunset seekers—the cooler parts of the day make walking more comfortable. If you’re traveling solo, with a partner, or even with friends who love a bit of storytelling mixed with sightseeing, this tour can be a highlight of your Key West trip.

However, if you’re looking for a fully guided experience with entrance tickets included, or want to visit specific sites inside, you might want to look elsewhere. This tour is about narrated walking exploration, not a traditional guided tour with a guide present.

The Pirates and Treasure: Self Guided Tour of Key West’s Old Town offers a fun, flexible way to unearth the island’s legendary past. Its engaging narration and wide range of stops make it perfect for history lovers and those wanting to explore at their own pace. For just under $30, you get a storytelling experience that brings Key West’s pirate legends to life, making history feel vibrant rather than dusty.

While it doesn’t include entry fees or transportation, the tour’s value lies in its storytelling and the freedom to roam. It’s especially suited for travelers comfortable with self-guided audio experiences who want a relaxed, immersive way to connect with Key West’s wild, treasure-filled history. If you’re after a casual, independent way to learn about pirates, shipwrecks, and legendary characters, this tour could be a memorable addition to your trip.

FAQ

Is this tour suitable for children?
Since the experience is self-guided and involves walking around historic sites, it’s generally suitable for older children who can follow along with the audio. However, the spooky stories and ghostly tales at places like Capt Tony’s Saloon might be better suited for teens or adults.

Do I need my own device and headphones?
Yes. The tour requires your smartphone and headphones to listen to the narration. The app provides offline access, so no need for internet once downloaded.

Can I start the tour at any time?
Yes, the tour is available 24/7, and your lifetime access means you can start whenever it’s convenient, whether early morning or just before sunset.

Are there any included tickets or entrance fees?
No, the tour does not include tickets to attractions. If you want to go inside sites like the Oldest House Museum or Mel Fisher’s Maritime Museum, you’ll need to purchase those separately.

How long does the tour take?
It typically lasts about 1 hour to 1 hour 15 minutes, but you can extend or shorten it depending on your pace and interests.

Is this a group tour?
No, it’s a private, self-guided experience. Only your group will participate, giving you flexibility and control over your exploration.

What’s the best time of day to do this tour?
Early mornings or just before sunset are ideal, as temperatures tend to be cooler and the lighting more atmospheric for photos and storytelling.

If you love stories of pirates and shipwrecks or prefer customizing your sightseeing experience, this tour offers a relaxed, fun way to connect with Key West’s storied past. Just remember to bring your device, plan for some walking, and enjoy discovering the legends that make this island so unique.