When it comes to exploring Savannah, the city’s charm lies not just in its architecture and squares but in its stories—some charming, some mischievous, and others downright heroic. The Savannah Cigar Crawl Rogues, Rascals, and Heroes offers a chance to enjoy these stories while savoring a cigar in the company of like-minded travelers.
We haven’t taken this tour ourselves, but based on the details and a glowing review, it seems like a wonderfully authentic way to experience the city’s past with a relaxed, social twist.
What makes this tour stand out? First, the combination of cigars and sightseeing creates a laid-back atmosphere that’s perfect for those who enjoy a leisurely stroll paired with good stories and a bit of smoke. Second, the small-group setting promises an intimate experience, making it easier to connect with the guide and other guests. However, one thing to consider is that the tour’s duration is just about 90 minutes.
While that’s enough time to enjoy a good walk and some tales, it’s a fairly quick taste of Savannah’s historic district.
This experience is ideally suited for travelers who want something different from the usual sightseeing tour. If you appreciate cigars, local history, and a more relaxed, social vibe, you’ll likely find this tour both fun and enriching. It’s also great if you’re traveling with a small group—up to ten people—and looking for a personalized touch in your Savannah explorations.
Key Points
- Unique combination of cigars and city history for a relaxed, immersive experience
- Small group size enhances interaction and a more personal touch
- Guided storytelling brings Savannah’s colorful characters to life
- Flexible cigar options—bring your own or buy at the start
- Ideal for cigar lovers and history buffs seeking a leisurely activity
- Affordable price point for a 1.5-hour intimate tour
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What to Expect on the Savannah Cigar Crawl
The tour begins at Ye Olde Tobacco Shop on East Bay Street, a fitting starting point for a tour centered around cigars and stories. From here, you’ll follow your guide past iconic landmarks like City Hall and the Customs House, which set a historic tone. The walk continues into Johnson Square, where Nathaniel Greene’s statue offers a glimpse into Savannah’s Revolutionary War past, as well as the charmingly historic Christ Church.
One of the highlights is walking through Wright Square, historically a courthouse square that once housed jail cells, gallows, and even a cemetery. This stop offers a peek into Savannah’s less glamorous history, with tales of rogues and heroes that evoke a sense of the city’s colorful past. As you stroll through these streets and squares, your guide shares stories of savannah’s rogues, rascals, and heroes, making history feel personal and vivid.
The tour culminates at Chippewa Square, famous for its movie fame (think “Forrest Gump”), where the group discusses more of Savannah’s local legends while finishing their cigars. The entire walk is designed to be accessible, with most travelers able to participate comfortably, and service animals are welcome.
You can also read our reviews of more tours and experiences in Savannah.
The Experience of Smoking and Sightseeing Together
What makes this tour particularly attractive is the combination of smoking a cigar and sightseeing. You can bring your own cigar or purchase one at the meeting point, which adds a layer of personalization. The relaxed pace allows you to enjoy your cigar while listening to stories, making it more than just a walking tour—it’s a social experience.
Hearing stories about Savannah’s rogues and heroes gives depth to the city’s streets. For example, the guide’s anecdotes about past characters and events turn the historic squares into living stories, not just static monuments. The fact that most reviews highlight the guide’s personable and entertaining manner suggests you’ll be in good hands, making the experience informative yet fun.
The Itinerary in Detail
The tour’s first stop at Ye Olde Tobacco Shop offers the chance to settle in and get your cigar ready. From there, the group heads out on a scenic stroll that covers key parts of Savannah’s historic core.
- City Hall and the Customs House: These buildings are impressive landmarks that set the tone for Savannah’s bustling history and commerce. The Customs House, with its grand architecture, hints at the city’s importance as a port.
- Johnson Square: The oldest and largest of Savannah’s squares, it’s home to Nathaniel Greene’s statue. Greene was a Revolutionary War hero, and his statue is a centerpiece that connects you to the city’s fight for independence.
- Christ Church: Built in the 18th century, this church adds a spiritual dimension, with history whispering through its walls.
- Wright Square: Once a site of public executions and jail, it’s a reminder of Savannah’s tougher days, now softened by stories and greenery.
- Chippewa Square: The tour wraps here; you’ll hear more tales while finishing your cigar. This square’s fame from movies adds a fun pop culture touch to the historic setting.
Throughout, the emphasis is on storytelling—highlighting colorful characters and notable events that define Savannah. You’ll love the way these stories humanize the city’s streets, making history feel accessible and engaging.
The Value of the Tour
At $35.90 per person, this tour offers a surprisingly good value. It’s a 90-minute guided walk, which is enough time to get a meaningful taste of Savannah’s historic downtown without feeling rushed or exhausted. The small group size—a maximum of ten—means fewer crowds, more personalized attention, and the chance to ask questions or share insights.
Being a mobile ticket adds convenience; no need to worry about last-minute bookings or waiting in lines. Since all fees and taxes are included, there are no hidden costs, and you can focus on enjoying your experience.
While alcoholic beverages are not included, the tour’s stop at a local pub (at your expense) provides a great opportunity to continue conversations or relax after the walk.
Authenticity and Review Insights
One reviewer enthusiastically called this tour “Highly recommended”, praising Neil, the guide, for being personable and entertaining. The review also notes the “nice stroll with a cigar and interesting stories,” which captures the essence of what this experience aims to be—a relaxed, storytelling-focused outing.
The small number of reviews, all highly positive, suggests that this tour’s charm lies in its personal approach. The guide’s ability to keep things engaging while sharing Savannah’s stories is a big plus. Many travelers appreciate the informal, friendly atmosphere—it’s less about grand monuments and more about connecting with the city’s characters and history.
Savannah Cigar Crawl Rogues Rascals and Heroes
Practical Details
The tour starts at 5:00 pm on East Bay Street, an ideal time to enjoy the cooler evening air and see the city’s squares light up. It ends at Chippewa Square, providing a convenient central location to continue exploring or head to dinner.
Most travelers will find this tour suitable, and service animals are allowed, making it accessible for visitors with pets. The tour’s cancellation policy is flexible—full refunds are available if canceled at least 24 hours in advance, giving peace of mind to planners.
If you enjoy history with a personal touch, this cigar crawl offers a memorable way to experience Savannah differently. It’s perfect for cigar enthusiasts wanting a more intimate, storytelling-focused tour, or travelers looking for a relaxed, social activity in the historic district. The guide’s personable style and the tour’s small size help create a genuine connection to Savannah’s past.
The price point makes it a great value for an engaging 90-minute outing, especially considering the personalized experience. If you want a taste of Savannah’s colorful characters, sprinkled with a bit of smoke and storytelling, this tour is well worth considering.
Can I bring my own cigar? Yes, you’re welcome to bring your own cigar to enjoy during the walk. Alternatively, you can purchase one at the start location.
What landmarks will I see during the tour? You’ll pass City Hall, the Customs House, Johnson Square, Christ Church, Wright Square, and finish at Chippewa Square.
How long does the tour last? Approximately 1 hour and 30 minutes, making it a manageable outing without a time commitment that’s too lengthy.
Is this tour suitable for all ages? Most travelers can participate, but it’s primarily geared toward adults due to the cigar aspect and the storytelling theme.
Are there any additional costs? All fees and taxes are included in the ticket price. However, drinks at the pub are at your own expense.
What is the group size? The tour is limited to a maximum of 10 travelers, ensuring a more personal experience.
Can I cancel if my plans change? Yes, full refunds are available if you cancel at least 24 hours in advance.
Is the tour accessible for service animals? Yes, service animals are allowed.
In all, the Savannah Cigar Crawl Rogues, Rascals, and Heroes offers a relaxed, story-filled way to see Savannah’s historic streets while enjoying a cigar and hearing colorful tales. If you’re looking for an authentic, intimate experience that mixes history, local legends, and good company, this tour might just be your perfect Savannah moment.
