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Experience Savannah's historic district with the Savannah Cigar Crawl, a 1.5-hour tour blending sightseeing, storytelling, and cigar-smoking for $35.90.
The Savannah Cigar Crawl Rogues Rascals and Heroes offers a unique way to explore Savannah’s historic district while enjoying a cigar. Priced at $35.90 per person and lasting approximately 1 hour 30 minutes, this guided walk promises an intimate experience with a small group of up to 10 travelers. Starting at the Ye Olde Tobacco Shop, the tour guides you through key landmarks such as City Hall, the Customs House, and Johnson Square—all while sharing colorful tales of Savannah’s rogues, rascals, and heroes. You can bring your own cigar or purchase one at the meeting point; the tour also features a stop at a local pub where you can buy a drink (own expense).
This tour is an engaging option for those looking to combine sightseeing and cigar enjoyment with storytelling about Savannah’s intriguing past. With a high rating of 5.0 based on a glowing review, it clearly appeals to visitors seeking a relaxed, personal experience led by a personable and entertaining guide. Keep in mind, the tour does not include alcohol, but the small group setup and interesting stops make it a memorable outing for those with a curious spirit and a love for history.


The tour kicks off at Ye Olde Tobacco Shop on 130 E Bay Street, a fitting starting point for a cigar-themed tour. Here, you have the option to bring your own cigar or purchase one at the shop, making it convenient for all cigar enthusiasts. The guide begins the walk at 5:00 pm, allowing for a relaxed evening exploration of Savannah’s historic core. The small-group format emphasizes an intimate atmosphere, perfect for engaging conversations and storytelling.
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As the walk progresses, the guide takes you past City Hall and the Customs House, two prominent buildings with architectural and historical significance. You’ll then stroll into Johnson Square, where Nathaniel Greene’s statue stands, and hear stories about the figures connected to the city’s past. The route also includes a visit to Christ Church, adding to the sense of walking through Savannah’s storied streets.

Next, the tour visits Wright Square, a location that once housed the jail, courthouses, gallows, and a cemetery. This site offers a glimpse into the city’s more turbulent history. The walk concludes at Chippewa Square, famous for its connection to the film “Forrest Gump,” but here, the focus remains on discussing Savannah’s rogues, rascals, and heroes. The group finishes their cigars at this last stop, soaking in the atmosphere of one of Savannah’s most iconic squares.

What makes this tour stand out is its blend of smoking a cigar amidst Savannah’s historic scenery while listening to fascinating tales. The storytelling aspect is a highlight, especially with a guide described as personable and entertaining. The experience feels genuine and warm, fostering conversations among like-minded travelers. The stop at a local pub for a drink (own expense) adds a social element, rounding out the experience.
The tour is easy to join with confirmed booking and a mobile ticket, starting promptly at 5:00 pm. It’s designed to be accessible to most travelers, with service animals allowed and a most travelers can participate message. The activity takes place in good weather, and if canceled due to poor conditions, a full refund or alternative date is offered. The cost covers all fees and taxes, with no extra charges except for drinks at the pub.
While only one review is available, it praises Neil Moore as a guide, describing him as very personable and entertaining. The small-group setting allows him to share interesting stories and create a lively, relaxed atmosphere. His storytelling style ensures that even complex or historical details are accessible, making the walk both educational and enjoyable.

This cigar crawl offers a different flavor compared to other Savannah tours like hop-on-hop-off trolley rides or ghost walks. It focuses on personal storytelling, landmark sightseeing, and cigar enjoyment, making it ideal for those who want a leisurely, engaging evening. For visitors interested in historic stories and local legends, this experience provides a memorable way to explore Savannah’s past.
The Savannah Cigar Crawl Rogues Rascals and Heroes stands out for its small-group intimacy, entertaining guide, and unique combination of cigars and storytelling. Its affordable price point and walk through iconic squares make it a compelling choice for those seeking an authentic, relaxed evening in Savannah. This experience is especially suited for history buffs, cigar lovers, and social travelers who appreciate storytelling set against Savannah’s beautiful backdrop.
While it doesn’t include drinks, the optional pub stop and the chance to enjoy Savannah’s sights and stories make it a well-rounded, enjoyable activity. If you seek a personalized tour that combines history, local legends, and cigar smoking, this tour offers a memorable introduction to Savannah’s colorful past.
“Neil was a great guide. Very personable and entertaining. A very nice stroll with a cigar and interesting stories about Savannah. Highly recomme…”
Can I bring my own cigar?
Yes, you are welcome to bring your own cigar for the tour.
Is the tour suitable for non-smokers?
Since the tour involves smoking cigars, it is best suited for those comfortable with cigar smoking or willing to partake during the walk.
What landmarks will I see during the tour?
The tour passes City Hall, Customs House, Johnson Square, Wright Square, and Chippewa Square.
How long does the tour last?
It takes approximately 1 hour 30 minutes.
Where does the tour start and end?
It begins at Ye Olde Tobacco Shop and finishes at Chippewa Square.
Is there an age limit?
Most travelers can participate, and service animals are allowed.
What is included in the price?
The price covers all fees and taxes; drinks at the pub are not included.
Can I cancel the tour?
Yes, there is free cancellation available up to 24 hours in advance.
Do I need to book in advance?
Yes, the tour requires confirmation at the time of booking and a mobile ticket.
What makes this tour different from other Savannah activities?
Its combination of cigar smoking and storytelling about Savannah’s colorful past in a small, intimate group sets it apart from more traditional sightseeing options.