Asheville: Roaring ’20s Walking Tour with Drinks

Taking a tour that combines history, local flavor, and a touch of the glamorous 1920s sounds like a fantastic way to spend an afternoon in Asheville. This Roaring ’20s Walking Tour with Drinks is designed for those curious about the era when speakeasies, gangsters, and handcrafted spirits dominated the scene. While I haven’t personally joined this tour, I’ve gathered enough details to give you a thorough look at what you can expect, what makes it special, and whether it’s worth your time and money.

What I really like about this experience is its focus on storytelling—learning about Asheville’s unique twist on the Prohibition era through an engaging guide—and the opportunity to taste signature cocktails in historic venues. Plus, it offers a paced walk through Asheville’s vibrant historic district, making it easy to soak in the sights while having fun. On the flip side, a possible consideration is the limited duration of just two hours—some may find it quick, especially if they love deep dives into history or spirits.

This tour is best suited for travelers who enjoy history, craft cocktails, and walking tours. It’s ideal if you’re looking for a relaxed, engaging way to explore Asheville’s past, with a social atmosphere that encourages mingling and tasting. It’s also suitable for those who appreciate knowledgeable guides and value authentic local experiences.

Key Points

• Historic focus: Learn about Asheville’s Prohibition era, gangsters, speakeasies, and local spirit production.
• Signature cocktails: Enjoy three house specialties at different venues, giving a taste of 1920s flair.
• Compact walk: The tour covers around 3 blocks, making it manageable for most fitness levels.
• Expert guides: Knowledgeable and entertaining guides add depth and personality to the experience.
• Limited to 21+: Not suitable for minors or pregnant women, due to alcohol consumption.
• Flexible cancellation: Free cancellation up to 24 hours before the tour, offering peace of mind.

You can check availability for your dates here:

An In-Depth Look at the Asheville Roaring ’20s Walking Tour

Setting the Scene: Asheville’s 1920s Charm

The tour begins in the heart of Asheville’s historic district, an area full of Victorian architecture and lively streets that echo the city’s past. As you step into this world, you’ll find yourself transported to the era when jazz was the soundtrack of nightlife, and secret bars thrived behind unassuming facades. The guide, often someone with personal or family stories—like Don, who can draw from firsthand experience—brings an authentic voice to the narrative.

The Itinerary: What’s Included and What to Expect

The tour spans roughly two hours, taking you through three renowned establishments that each played a role in Asheville’s Prohibition scene. The walking distance is modest—about three blocks—so it’s accessible without being strenuous. Expect to move at a comfortable pace, with plenty of time to hear stories, ask questions, and enjoy your drinks.

First Stop: Introducing the Era

The initial venue often sets the tone, perhaps a historic bar that has preserved its 1920s ambiance. Here, your guide will share tales of gangsters, speakeasies, and the local efforts to keep spirits flowing during Prohibition. The stories are filled with trivia and colorful anecdotes, making history come alive in a way that’s both educational and entertaining.

More Great Tours Nearby

Second and Third Venues: Tasting and Storytelling

At each subsequent stop, you’ll get to enjoy a signature cocktail, carefully crafted to evoke the spirit of the Roaring ’20s. These drinks are house specialties, giving you a taste of local craftsmanship and era-appropriate flavors. The venues are chosen not just for their drinks but for their historical significance, often with a charming old-world atmosphere.

The Guides: Knowledge and Entertainment

Reviews highlight guides like Don, who is both knowledgeable—drawing from personal family history—and engaging. Their storytelling skills help paint a vivid picture of the era, making facts memorable and fun. You’ll likely learn about Asheville’s history of handcrafted spirit production, which adds a layer of authenticity to the experience.

The Cost and Value

At $99 per person, the tour offers a good balance between price and value. You’re getting three signature cocktails, access to historic venues, and insights from a guide. While it’s a short experience, the combination of storytelling and tasting provides a well-rounded glimpse into Asheville’s past. It’s particularly appealing if you’re seeking a conversational, relaxed activity rather than a full-day tour or museum visit.

Considerations: What Could Be Better?

One downside for some might be the short duration—only two hours—which limits how deeply you can explore the history. Also, since hotel pickup and drop-off are not included, you’ll need to plan your transportation to and from the meeting point. For those unfamiliar with the area, this could be a minor inconvenience but not a dealbreaker.

Practical Tips for Participants

Bring your ID or passport, as proof of age is needed for alcohol consumption. Be prepared for short walks (about three blocks total); comfortable shoes are advised. Since the tour is only available in the afternoon, it pairs well with a leisurely day of sightseeing afterward. If you have dietary restrictions or low alcohol tolerance, consider that you’ll be sampling three cocktails.

What the Reviews Say

While the overall rating is 4.2 out of 5 based on five reviews, experiences vary slightly. One reviewer from August expressed disappointment about a no-show, which underscores the importance of confirming your reservation. Conversely, another reviewer praised the knowledgeable guide and the variety of drinks, emphasizing how much they enjoyed the storytelling and the engaging pace.

Who Will Love This Tour?

This experience is best suited for history enthusiasts, especially those interested in the Prohibition era, as well as cocktail lovers eager to taste local and era-inspired drinks. It’s also perfect if you prefer small, intimate groups and storytelling over large, noisy tours. Since it’s accessible and wheelchair friendly, most travelers can participate.

Who Might Not Enjoy It?

People under 21, pregnant women, or those seeking a more in-depth or longer tour might find it too brief or limited. Also, travelers expecting a more hands-on spirits tasting—like distillery visits—should look elsewhere.

Final Thoughts

This Asheville Roaring ’20s Walking Tour offers a charming and flavorful glimpse into the city’s past. It strikes a good balance of history, local flavor, and social fun, making it an excellent choice for those wanting a light, engaging experience. The knowledgeable guides bring stories to life, and the signature cocktails add a real taste of the era. Its affordability and ease make it an attractive option for most visitors.

If you’re keen on learning about Asheville’s history through lively storytelling while enjoying a couple of well-crafted drinks, this tour should fit the bill. It’s especially well-suited for history buffs, cocktail aficionados, and anyone curious about the city’s unique flavor during the Roaring ’20s.

FAQ

Is the tour suitable for people with mobility issues?
Yes, since the walk is only about three blocks in total, it’s manageable for most. The tour is wheelchair accessible, making it more inclusive.

What’s included in the price?
You get a guided walk, stops at three venues, and three signature cocktails. No transportation or hotel pickup is included.

Can I cancel my booking?
Yes, you can cancel for a full refund if you do so at least 24 hours in advance.

Is this tour available in the morning or only in the afternoon?
It’s usually available in the afternoon, fitting well into a relaxed day of sightseeing.

Do I need to bring anything special?
Just your ID or passport to prove your age. Comfortable shoes are recommended for the short walk.

Are children allowed on this tour?
No, the experience is not suitable for minors or pregnant women due to alcohol consumption.

How many people typically join the tour?
While the exact group size isn’t specified, the small size suggested by the intimate tasting experience is likely typical.

What if I have dietary restrictions?
Since the cocktails are house specialties, it’s best to inform the provider ahead of time if you have specific restrictions. However, alcohol is a central part of the tour, so options may be limited.

In summary, the Asheville Roaring ’20s Walking Tour with Drinks offers a lively, authentic taste of the city’s vintage past. It’s a great pick for those looking to combine history, local culture, and a few drinks into a manageable, enjoyable experience.

You can check availability for your dates here: More Great Tours Nearby