Charleston Women and Wine Tour

Taking a tour that blends history, culture, and a touch of wine sounds like a perfect way to spend an afternoon in Charleston. While I haven’t personally experienced this tour, the glowing reviews and detailed itinerary paint a picture of a unique and engaging experience. Designed by locals Gia and Capt. Bryan, this tour offers an immersive look into the women who shaped Charleston’s political, social, and economic landscape — all with a casual, fun vibe.

What we love about this experience is its focus on women’s stories often overlooked in traditional tours, the opportunity to support female entrepreneurs through the wine stops, and the small group setting which promotes intimacy and engagement. On the flip side, a potential consideration might be the walkability — some parts involve uneven walkways in the historic district, which might be challenging for guests with walking difficulties.

This tour is ideal for history buffs eager to learn about influential women, wine lovers wanting to combine culture with a drink, or travelers seeking a balanced mix of education and entertainment in Charleston’s charming streets. If you fall into any of these categories, this tour could be a highlight of your visit.

Good To Know

• Focus on Women’s History: The tour spotlights influential women in Charleston’s past, providing fresh perspectives often missed elsewhere.
• Two Bar Stops & Historic Sites: Combines cultural storytelling with relaxed wine or cocktail breaks at women-owned establishments.
• Expert Guides: Gia and Capt. Bryan are praised for their storytelling skills, making history engaging and accessible.
• Small Group Experience: With a maximum of 10 people, expect personalized attention and lively conversations.
• Affordable for Value: At $34 per person, the tour offers a well-rounded, immersive experience for a reasonable price.
• Inclusive & Accessible: While most travelers will enjoy this, those with walking difficulties should note the uneven walkways in the historic district.

The Itinerary Breakdown: What to Expect Step-by-Step

Stop 1: St. Philip’s Church

Your journey begins at one of Charleston’s oldest congregations. The Historical Graveyard and Cemetery here are packed with stories of notable figures who left their mark on the city. Expect to learn about the pioneers and powerful personalities buried there, setting a reflective tone for the tour. Reviewers mention that Gia’s storytelling at this stop is captivating, with one noting her passion for sharing Charleston women’s stories vividly.

Stop 2: St. Michael’s Church

Next, you’ll visit this oldest church edifice still standing, situated at the famed Four Corners of Law. Here, the focus shifts to women who challenged societal norms and faced adversity head-on. The short five-minute stop offers a glimpse into the forces that opposed these women, with many reviewers praising Gia’s ability to make history come alive. Expect to hear tales of resilience and defiance that highlight Charleston’s pioneering women.

Stop 3: Heyward-Washington House

This historic residence, linked with notable (and sometimes controversial) owners, played a role in abolitionism. The house offers a window into the complex dynamics of its time, and the guide explains the pivotal role of past residents in the fight for freedom. Many reviews praise Gia’s detailed knowledge, especially about the abolitionists who once called Charleston home.

Passing by Art & Architectural Landmarks

As the tour proceeds, you’ll pass by a prominent art museum, crafted by one of the women discussed during the tour. The route also takes you past stunning architecture, including the oldest Gothic Revival building in South Carolina — a nod to the international influence of women in Charleston’s history, especially those with French ties. Reviewers appreciate the rich context given about these landmarks, tying them to the women’s stories.

Final Stop: Second Bar Visit

The tour concludes at the Blind Tiger Pub, a lively spot less than three blocks from the starting point. Here, guests can purchase drinks — from wine to cocktails — to toast their newfound knowledge. Reviewers highlight that the hosts recommend excellent bars and provide helpful tips on what to order, making this a relaxed, social ending to a culturally enriching experience.

What’s Included & What You Should Know

Included:

• A licensed guide with a knack for storytelling, passionate about Charleston’s women’s history.

Not Included:

• Drinks are not included in the tour fee but are available for purchase at the bar stops. Guests are encouraged to enjoy a glass of wine, beer, or cocktail, supporting women entrepreneurs.

Duration & Group Size:

• About 2 hours of walking and storytelling, with a maximum of 10 guests — perfect for intimate conversations and personalized attention.

Timing & Meeting Point:

• Tour starts at 4:00 pm from 49 S Market St and ends near Broad Street, close to the start.
• The walk covers approximately 1.5 miles, with uneven brick walkways in some sections, so comfortable shoes are recommended.

Age & Accessibility:

• Must be 21+ to purchase alcohol; the tour is generally inclusive but may pose challenges for those with walking difficulties due to the district’s uneven terrain.

Authentic Experiences and Authentic Guides

Many reviewers have raved about Gia’s storytelling abilities, describing her as passionate, engaging, and knowledgeable. One reviewer even mentioned Gia’s expertise in architecture, which added an extra layer of richness to the experience. Capt. Bryan’s storytelling and personable style also received high praise, with guests feeling genuinely connected to the stories of Charleston’s women.

Reviewers specifically appreciated the non-traditional focus on women’s herstory, highlighting stories of pioneering women active during Prohibition, abolition, and social reform. The tour doesn’t just recount facts; it brings these stories to life through vivid narratives, making history relatable and memorable.

The small group size fosters a cozy, interactive atmosphere, encouraging questions and discussions. Guests also noted the fun, relaxed vibe at the bar stops, where they could enjoy a drink without feeling rushed.

An Honest Look at Value

At $34, this tour offers a lot — a mix of history, culture, and casual socializing. The price doesn’t include drinks, but reviews indicate that the suggestions from guides are well worth exploring. The opportunity to support women-led businesses while learning about influential women in Charleston adds a layer of social value to the experience.

Compared to traditional walking tours that focus solely on architecture or general history, this one stands out by centering often overlooked women’s stories. Several guests mentioned how this focus made the tour feel fresh and meaningful, especially during Women’s History Month or special occasions.

Who Will Love This Tour?

This experience is perfect for history enthusiasts interested in gender stories, culture vultures who enjoy authentic local experiences, and wine lovers looking to combine education with relaxation. It suits travelers who appreciate small-group tours for a more personal feel and those interested in supporting local, women-owned businesses.

While the walk covers roughly 1.5 miles, it’s suitable for most physically able guests who enjoy light walking and historical storytelling. If you love discovering hidden stories behind well-known landmarks, this tour will satisfy your curiosity with colorful anecdotes and expert insight.

Final Thoughts

The Charleston Women and Wine Tour offers a compelling mix of historical education, local flavor, and casual socializing. Led by passionate guides Gia and Capt. Bryan, the experience shines through their storytelling prowess and genuine enthusiasm for Charleston’s women’s stories.

You’ll walk away with a deeper understanding of the women who helped shape Charleston, from abolitionists to social reformers, all while enjoying the laid-back atmosphere of local bars. The small group size ensures an intimate, engaging experience that’s both educational and fun — and at just $34, it’s an excellent value.

Whether you’re a history buff, a wine lover, or simply seeking a different way to experience Charleston, this tour offers a memorable journey into the city’s herstory you won’t forget.

FAQs

Is this tour suitable for all ages?
No, guests must be 21+ to purchase alcohol, but the storytelling and historic sites are suitable for most adults.

How long does the tour last?
The tour is approximately 2 hours, including stops and walking.

Are drinks included in the price?
No, drinks are not included but can be purchased at the bar stops; guides will recommend good options.

What should I wear?
Comfortable walking shoes are recommended due to uneven walkways; casual attire is perfect.

Is the tour accessible for people with walking difficulties?
While most of the walk is manageable, some parts involve uneven brick walkways which may be challenging.

Where does the tour start and end?
It begins at 49 S Market St and ends near Broad Street, less than three blocks from the start.

Can I cancel if I change my mind?
Yes, cancellations are free if made at least 24 hours in advance. Less than 24 hours, and the refund is not available.

Are the guides knowledgeable?
Absolutely, reviews highlight Gia’s storytelling skills and her deep knowledge of Charleston’s women’s history.