Savannah Cigar Crawl Rogues Rascals and Heroes

If you’re wandering Savannah and want to combine a leisurely walk through its charming streets with a bit of indulgence, the Savannah Cigar Crawl Rogues Rascals and Heroes offers a pretty distinctive way to experience the city. While I haven’t done this tour myself, the reviews and details paint a picture of an intimate, engaging outing that’s perfect for those who enjoy history, good company, and a fine cigar or two.

What really catches my eye about this experience is how it seamlessly blends sightseeing with socializing—you get to stroll past Savannah’s famous landmarks while chatting about the colorful characters who shaped the city. Plus, the small-group setting promises a more personal touch. On the flip side, it’s a short tour—just about an hour and a half—so it’s definitely a quick hit rather than a deep dive. This tour seems best suited for travelers who want a relaxed, unpretentious way to soak up some local stories and enjoy a cigar in good company.

Key Points

• Small Group Size: Intimate experience with up to 10 travelers, making for personal interactions.
• Rich Local Stories: Focus on Savannah’s characters—rogues, rascals, and heroes—adding flavor to the walk.
• Flexible Cigar Options: Bring your own or purchase one at the meeting spot, catering to casual cigar lovers.
• Affordable Price: At around $36 per person, it offers a unique experience without breaking the bank.
• Prime Location Start: Begins at Ye Olde Tobacco Shop, in the heart of Savannah’s historic district.
• Ideal for History & Cigar Enthusiasts: Perfect if you love stories with a laid-back vibe and enjoy a good smoke.

An Honest Look at the Cigar Crawl

This tour is designed to be a relaxed, social walk through Savannah’s historic district, where the main draw isn’t just the sights but also the stories—and, of course, the cigars. The tour is limited to about 10 travelers, which means it keeps the group small enough that you can really get a feel for the experience and have plenty of chances to chat with the guide and fellow participants.

Starting point at Ye Olde Tobacco Shop, you’ll gather at 5 pm, a convenient evening hour that lets you enjoy Savannah’s cooler temps and lively atmosphere. The tour lasts approximately 90 minutes, which is just enough time to cover several key landmarks without feeling rushed.

The Itinerary

The route takes you through some of Savannah’s most iconic spots, starting with the Ye Olde Tobacco Shop, where you can either bring your own cigar or pick one up at the shop. From there, you’ll walk past City Hall and the Customs House, both impressive buildings with stories of their own. As you stroll, you’ll see Johnson Square, home to Nathaniel Greene’s statue, and Christ Church, adding historical depth to your walk.

The next stop is Wright Square, which has a darker past—used in days gone by for jail, gallows, and cemetery activity. It’s a spot that sparks curiosity about Savannah’s more colorful past. The last major stop is Chippewa Square, famous for its cinematic history (think the park bench scene from Forrest Gump) and as the final point of the tour, where you’ll finish your cigars amid the lively ambiance of the square.

What’s Included and Not

The tour fee covers all fees and taxes, so no hidden costs. You’ll need to handle your own alcoholic beverages if you want a drink at the local pub stop, which is on your own tab. Since the focus is on cigars and stories, it’s a flexible experience that allows you to enjoy your own preferred drink separately.

How It Works

When you book, you’ll get a mobile ticket and confirmation immediately, making last-minute plans straightforward. The tour is suitable for most travelers, and service animals are welcome if needed. It’s a laid-back, conversational experience, perfect for those who want a personal touch and an authentic local vibe.

The Experience of Smoking and Sightseeing

One of the coolest aspects of this cigar crawl is the combination of a walking tour with a relaxed cigar-smoking environment. Walking around Savannah’s beautiful streets while puffing on a cigar might sound unconventional, but it’s actually a great way to slow down and savor the moment. The guide shares stories about Savannah’s rogues, rascals, and heroes, making history feel lively and colorful.

According to the glowing review from a Tripadvisor visitor, Neil, the guide, is “very personable and entertaining,” which really makes a difference when you’re sharing stories and enjoying a leisurely stroll. The review also mentions that it’s “a very nice stroll with a cigar and interesting stories,” highlighting how relaxed and engaging the experience is.

The Stops and Their Significance

Each stop is carefully chosen to give you a taste of Savannah’s past. The City Hall and Customs House are striking buildings with fascinating histories, while Johnson Square acts as a hub of history with its notable statue. Moving into the Wright Square area, the tour touches on the more gruesome aspects of Savannah’s past, with references to its jail, gallows, and cemetery, giving a sense of the city’s layered history.

Finally, the tour culminates at Chippewa Square, a fitting spot to finish your cigars and chat about Savannah’s heroes and villains. This square’s fame from Hollywood lends a fun, cultural touch to the experience.

Analyzing the Value

At roughly $36 per person, this tour offers a unique way to see Savannah’s historic district while enjoying a cigar in good company. Compared to other sightseeing options that might cost more and be less personal, this experience delivers value through its combination of storytelling, intimacy, and relaxed pace. Plus, it’s an activity that’s likely to appeal more to adults, especially those who appreciate cigars and history.

What Travelers Love

Most reviews highlight the knowledge and charisma of the guide. Neil, the guide, is praised for being “very personable and entertaining,” making the walk informative yet fun. The personal touch and the stories about Savannah’s “rogues, rascals, and heroes” add a layer of authenticity that many find refreshing.

However, it’s worth noting that the tour is short, and if you’re expecting a deep dive into Savannah’s entire history, you might want to supplement this experience with other tours. This is more about a fun, social exploration of the city’s colorful characters and stories.

Who Will Love This Tour?

This cigar crawl is best suited for adults who enjoy a relaxed, small-group experience. It’s ideal for history buffs interested in Savannah’s characters, or travelers who want a more laid-back way to see the historic district without the hustle of large bus tours. If you appreciate stories told by engaging guides and like the idea of combining a walk with cigar smoking, this is a solid choice.

It’s also a good fit if you’re traveling as a couple or small group and want an intimate, conversational outing. Not so much for families or children, unless they’re older and cigar-enthusiasts themselves.

Final Thoughts

All in all, the Savannah Cigar Crawl Rogues Rascals and Heroes offers a unique spin on sightseeing—an enjoyable blend of storytelling, history, and cigars. It highlights local legends and historic landmarks in a relaxed setting, making it perfect for those who want to experience Savannah’s colorful past without the fuss.

While it’s not a lengthy or exhaustive tour, it excels at providing a memorable, personal experience that’s easy to fit into an evening. The small group size and charismatic guide make it especially appealing for travelers craving authenticity and connection.

If you’re into cigars, storytelling, and Savannah’s historic charm, this tour is definitely worth considering. Just remember, if you’re looking for a deep historical deep dive or a longer activity, you might want to explore other options. For a fun, intimate evening with a touch of local legend, this cigar crawl delivers.

FAQ

Can I bring my own cigar?
Yes, you’re welcome to bring your own cigar or purchase one at the meeting spot, Ye Olde Tobacco Shop.

What is the tour duration?
The tour lasts approximately 1 hour and 30 minutes, making it a perfect short activity for an evening.

Where does the tour start and end?
It begins at Ye Olde Tobacco Shop on East Bay Street and ends at Chippewa Square in the heart of Savannah.

Is this tour suitable for children?
This tour is designed for adults, especially those who enjoy cigars and storytelling. It’s not specifically geared toward children.

What’s included in the price?
All fees and taxes are included. You will need to cover your own expenses if you want a drink at the pub stop.

Is the tour weather-dependent?
Yes, it requires good weather. If canceled due to rain or bad weather, you’ll be offered a different date or a full refund.

How many people are in each group?
The tour is limited to a maximum of 10 travelers, ensuring a more personal experience.

Hopefully, this gives you a clear picture of what to expect from the Savannah Cigar Crawl. It’s a charming way to enjoy the city’s stories and scenery in a relaxed, friendly setting. If this sounds like your kind of adventure, it’s worth adding to your Savannah list.