Savannah Cigar Crawl Rogues Rascals and Heroes: An Informative Guide

Imagine strolling through Savannah’s storied streets, cigars in hand, while uncovering tales of local rogues, rascals, and heroes. For just $35.90 per person, you get an approximately 1 hour and 30 minutes journey that mixes sightseeing, storytelling, and cigar culture. Led by a personable guide—Neil, according to glowing reviews—you’ll visit iconic landmarks like City Hall, Johnson Square, Wright Square, and even enjoy a stop at a local pub. The tour begins at the historic Ye Olde Tobacco Shop on Bay Street and finishes at Chippewa Square, famous for its movie connection and the statue of General Oglethorpe.
Two things we really like about this experience are its small-group intimacy—max 10 participants—which fosters a more personal atmosphere, and the chance to combine cigar smoking with sightseeing, unusual but surprisingly enjoyable. The guide’s storytelling skills make the history come alive—adding both humor and local flavor. A potential drawback? If you’re not a cigar enthusiast or prefer a more structured tour, this might not be your first choice. But for those who appreciate cigars and colorful tales, it’s a perfect fit.
This tour suits travelers who enjoy authentic local stories, relaxed atmospheres, and want a unique way to explore Savannah’s historic district. It’s particularly appealing for cigar lovers or anyone wanting to experience Savannah from a different perspective—combining leisure with culture.
Key Points

- Authentic Experience: Combines cigar smoking with historical storytelling in Savannah’s historic district.
- Personalized Atmosphere: Small group tour (max 10) for more engaging interaction.
- Flexible Cigar Options: Bring your own or purchase one at the meeting point.
- Rich Narrative: Tales of Savannah’s colorful characters add depth to the sights.
- Ideal for Enthusiasts: Perfect for those who appreciate cigars and local history.
- Easy to Book & Cancel: Mobile tickets and free cancellation up to 24 hours in advance.
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Exploring Savannah’s Hidden Stories on Foot with a Cigar

Walking through Savannah’s historic district, with a cigar in hand, is a surprisingly fitting way to experience the city’s charm. The tour, guided by Neil, begins at Ye Olde Tobacco Shop, a fitting starting point for cigar aficionados and curious travelers alike. We loved the way Neil seamlessly combines local history, colorful anecdotes, and a relaxed pace, making the experience both informative and enjoyable.
The Itinerary: Step-by-Step Through Savannah’s Past
First stop: From Ye Olde Tobacco Shop, your stroll begins by passing City Hall and the Customs House. These landmarks are more than just impressive buildings—they’re symbols of Savannah’s long-standing role as a port city. As you walk, Neil shares stories of the city’s rogues and rascals, setting the tone for the tour. We appreciated the way he brought history to life with vivid tales, which kept us engaged amid the historic surroundings.
Next, Johnson Square: home to the statue of Nathaniel Greene, a Revolutionary War hero. Here, you’ll get a sense of Savannah’s early importance and its roots in American history. The tour moves on to Christ Church, one of Savannah’s oldest and most beautiful churches, adding architectural beauty to the mix.
Wright Square: Known as the courthouse square in earlier days, it once housed jails, gallows, and cemeteries. Neil’s stories about this darker side of Savannah’s past provided a fascinating contrast to the charming streets. The tour’s narrative helps you appreciate the layers of history beneath the city’s picturesque facade.
Final stop: At Chippewa Square, famous for its appearance in “Forrest Gump,” the group winds down while discussing more local legends and the city’s heroes. This is where most participants finish their cigars, giving a relaxed close to an engaging walk.
What Makes This Tour Special?
What sets this experience apart is the blend of cultural sightseeing with cigar enjoyment. Unlike typical walking tours, this one invites you to smoke your own cigar or buy one at the start, making it more personal and leisurely. The stories, delivered with humor and insight, transform a simple walk into a rich narrative. The small size of the group ensures a more intimate experience, allowing for questions and personal interactions.
The Value of a Guided Cigar Stroll
At just $35.90, this tour offers remarkable value. It’s not just a sightseeing outing but a chance to connect with Savannah’s past in a relaxed, unpretentious way. The inclusion of all fees and taxes simplifies the booking process, and the ability to cancel for free up to 24 hours before means no worries if your plans change.
Authenticity & Atmosphere: Why It Matters
The charm of this tour lies in its authenticity. Neil’s storytelling skills, as praised in reviews, make the history more relatable, injecting humor and local color that stick with you long after the tour ends. The small group size fosters a cozy environment, perfect for conversation and shared experiences—especially if you’re traveling solo or in a small group.
Why This Tour Works for You
If you enjoy learning about history through stories, this tour is ideal. It suits those who want to experience Savannah’s historic district beyond just taking photos, blending history with casual cigar smoking. It’s especially suited for adventurous travelers who enjoy local flavors, and those who appreciate personalized, relaxed tours.
The Practical Details: What You Need to Know

The tour starts at 5:00 pm, a great time to enjoy Savannah’s cooler evening air. The meeting point at Ye Olde Tobacco Shop is central, making it easy to access from other parts of the city. The tour lasts about 90 minutes, which is enough time to enjoy a leisurely walk without feeling rushed.
Group size: Limited to 10 travelers, ensuring personal attention and a relaxed vibe.
Inclusions: All fees and taxes, with the option to bring your own cigar or buy one at the start.
Not included: Alcoholic beverages, although the tour includes a stop at a local pub where you can purchase drinks yourself.
Weather considerations: As an outdoor walking tour, bad weather might result in cancellation or rescheduling, with full refunds offered.
Summing It Up: Is the Savannah Cigar Crawl Right for You?

This tour offers a unique blend of history, storytelling, and cigar culture in the heart of Savannah. It’s especially ideal if you’re someone who enjoys a relaxed pace, authentic local tales, and the simple pleasure of smoking a cigar while exploring a beautiful city. The knowledgeable guide, Neil, makes the experience engaging and memorable—many past travelers describe him as personable and entertaining.
If your idea of exploring a city includes small-group conversations and regional stories, you’ll find this tour to be a delightful addition to your Savannah itinerary. It’s also a good choice if you want a less commercial, more personal experience that combines leisure with cultural insight.
Frequently Asked Questions
Can I bring my own cigar? Yes, you can bring your own cigar or purchase one at the meeting point.
How long does the tour last? About 1 hour and 30 minutes, giving you a relaxed walking experience.
Where does the tour start and end? It begins at Ye Olde Tobacco Shop and finishes at Chippewa Square in Savannah.
Is there a minimum or maximum group size? Yes, the tour is limited to 10 travelers, ensuring an intimate experience.
Are tips included? Tips are not included; gratuities are appreciated if you enjoy the guide’s storytelling.
What is the cost? The tour costs approximately $35.90 per person, including all fees and taxes.
Can I cancel if my plans change? Yes, free cancellation is available up to 24 hours before the tour.
Is this tour suitable for children? Most travelers can participate, but it’s best suited for adults or older teens who appreciate cigars and history.
Do I need to prepare anything? Just bring your cigar if you have one, and wear comfortable walking shoes for the historic district.
Final Thoughts
In sum, the Savannah Cigar Crawl Rogues Rascals and Heroes offers a distinctive way to experience Savannah. It combines the city’s colorful past with the relaxing pleasure of smoking a cigar in a small, friendly group. The stories Neil shares add depth and fun, making it more than just a walk—it’s an engaging journey through Savannah’s lively history.
This tour is well-suited for those who value authentic storytelling, relaxed atmospheres, and are curious about Savannah’s lesser-known tales. It’s perfect for history buffs, cigar lovers, and travelers seeking a more personal connection to the city’s vibrant past.
Whether you’re a solo adventurer, a couple, or a small group, this experience offers a memorable way to deepen your appreciation of Savannah—and enjoy a good cigar while you’re at it.
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