Charleston: Women and Wine Tour

If you’re looking for a unique way to explore Charleston’s historic streets while celebrating the women who shaped its past, the Women and Wine Tour might just be what you need. Designed and led by two passionate local historians, this experience blends storytelling with visits to historic bars, offering a different kind of sightseeing—and one that’s both educational and fun.

What immediately appeals to us is how this tour emphasizes women’s contributions to Charleston’s social, political, and economic life—rarely covered in traditional city tours. Plus, the opportunity to visit two historic bar locations, each with its own stories, adds a lively and relaxed vibe to an otherwise serious history route.

One thing to keep in mind is that drinks are not included in the price, so you’ll want to budget additional for beverages if you plan to enjoy the stops fully. The tour is best suited for adults who are interested in history, women’s stories, and a bit of local bar-hopping—all wrapped into a 2-hour package that feels more like a social event than a standard history walk.

This experience seems well-suited for those who appreciate storytelling, enjoy lively small-group atmospheres, and want a more personal, guided insight into Charleston’s legacy of influential women. If that sounds like your cup of tea (or glass of wine), it’s worth considering.

You can check availability for your dates here:

Key Points

• Focused on women’s history and influential figures in Charleston.
• Led by licensed local historians Gia and Capt. Bryan, offering expert insights.
• Includes two historic bar stops, with opportunities for drinks (not included).
• Passes by and discusses historic sites in the downtown district.
• Casual, small-group tour limited to 10 participants for a personalized experience.
• Two hours long, usually in the afternoon—perfect for a relaxed, engaging outing.

This tour combines the best of both worlds: a walk through Charleston’s iconic streets intertwined with stories about women who made a difference, plus stops at historic bar venues that bring a lively ambiance to the experience.

Starting at Well Hung Vineyard

The tour kicks off at Well Hung Vineyard, located at 49 S Market Street. This spot is a fitting starting point—they serve wine, beers, and cocktails, and are run by women entrepreneurs, which ties into the theme perfectly. Here, you’ll likely get introduced to women active during Prohibition, adding a layer of historical intrigue. The staff are friendly and helpful in getting everyone settled and ready for the journey.

The Route and Historic Highlights

From there, your guides lead you through the historic district, pointing out sites linked to influential women of Charleston. You can expect to hear stories of adversity and strength—tales that celebrate resilience and impact. The route is designed not just as a walk but as a narrative experience, where each stop or passing site adds to the picture of women’s roles in shaping the city.

The Bar Stops

The highlight for many is the two bar locations, which are part of the experience. One is a quaint, historic venue that’s steeped in Charleston’s past, while the other offers a quirky, lively atmosphere. These stops aren’t just about drinks—they’re about ambience, stories, and connecting the history to the present. While drinks are not included in the ticket price, you’ll have the chance to order wine, beer, or cocktails, making the experience more social and relaxed.

More Great Tours Nearby

What You’ll Learn

Guided by Gia and Capt. Bryan, who are both licensed historians, you’ll get a mix of factual history and lively anecdotes. From women involved in the Prohibition era to those who broke social barriers, the stories shared tend to inspire and educate. As one reviewer commented, Gia was “awesome” and made the history “so inspiring,” emphasizing her engaging storytelling style.

The Final Stop

The tour wraps up back at the second bar, giving everyone a chance to unwind and reflect. Many guests appreciate that this isn’t just a walk-and-talk but an experience that balances education, socialization, and local flavor.

We loved seeing how the tour captures Charleston’s spirit—its history, its women’s stories, and its vibrant bar scene—all woven together in a casual, approachable manner. The two-hour length makes it a perfect afternoon activity, allowing you to fit it into a day of exploring the city.

The small group size means you get plenty of one-on-one interaction with your guides, which is especially valuable for learning detailed stories. Plus, having local historians leading the tour offers authentic insights you might not find in guidebooks or standard tours.

The price point of $34 per person seems reasonable, especially considering the personalized storytelling and small-group setup. However, since drinks are not included, if you plan to indulge at the bar stops, budget extra—though this gives you the flexibility to choose what and how much to drink.

What the Reviews Say

Guests consistently praise Gia’s knowledgeable and friendly manner. One reviewer noted, “Gia was very knowledgeable and friendly,” and another said she was “an incredible guide” who shared “so many stories of influential women.” The enthusiasm for her storytelling is palpable.

Many mention how inspiring and surprising the stories were, with one commenting, “I left feeling inspired and grateful to be a woman.” The combination of storytelling, history, and local drinks seems to resonate well with participants.

Practical Considerations

The tour is rain or shine, so be prepared with weather-appropriate gear. It’s not suitable for pregnant women or those with mobility issues, as the walk involves some passing by historic sites and the potential for uneven terrain. Make sure to bring your ID or passport, as required for age verification.

Parking is convenient at Cumberland Garage, just a short walk away, which makes logistics easier for those driving into town.

This experience is ideal for adults interested in history, women’s stories, and local culture. It’s especially good for those wanting an interactive, social outing with a focus on storytelling rather than just sightseeing. Couples, friends, or solo travelers who enjoy small-group settings will find it more personal and engaging.

It’s also perfect if you want to combine a light drink and a little education without dedicating a whole day. However, if you’re traveling with mobility issues or prefer more extensive walking, this might not be the best fit.

The Women and Wine Tour in Charleston offers a unique, friendly, and insightful way to discover the city’s history through the lens of influential women. Led by passionate local guides, it balances engaging storytelling with visits to historic bars, making it both entertaining and educational. The two-hour format makes it a manageable yet meaningful addition to your Charleston itinerary.

It’s best suited for curious travelers who enjoy learning about social change, local stories, and a touch of nightlife—all in a small, intimate group. The absence of included drinks allows you to customize your experience, making each visit feel relaxed and personal.

If you’re looking for a fun, meaningful way to spend an afternoon in Charleston that combines history, women’s contributions, and a little social flair, this tour is worth considering. It’s a good value for the quality of storytelling and local insights you’ll gain, especially if you appreciate a casual, personable guide and a friendly atmosphere.

Do I need to bring anything?
Just your ID or passport for age verification. Comfortable shoes are recommended since you’ll be walking around historic sites.

Are drinks included in the tour?
No, drinks are not included. You’ll have the chance to purchase wine, beer, or cocktails at the stops, allowing you to decide how much you want to indulge.

Is the tour suitable for children or families?
No, guests must be 21+ for this tour, as it involves alcohol stops and an adult-oriented theme.

How long does the tour last?
It’s a 2-hour experience, usually scheduled in the afternoon, making it easy to slot into a day of sightseeing.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, offering some flexibility if your plans shift.

Is parking available nearby?
Yes, closest parking is at Cumberland Garage, just around the corner from the meeting point.

What is the group size?
Limited to 10 participants, ensuring a more intimate and personalized experience.

Would this tour be good for people interested in history?
Absolutely—it’s led by licensed historians, and the stories highlight key women who shaped Charleston’s past, making it perfect for history buffs.

You can check availability for your dates here: