Sinfully Delicious Dessert Tour: A Sweet Walk Through Charleston’s Historic Streets

If you’re craving a unique way to experience Charleston, this Sinfully Delicious Dessert Tour offers an engaging blend of history, sweet treats, and southern spirits. With a moderate price of $175 per person, it’s a 2-hour stroll through the cobblestone streets of the historic district led by an expert local guide. Along the way, you’ll visit a striking 19th-century neoclassical building on East Bay Street, and indulge in a curated selection of Lowcountry desserts paired with signature Southern cocktails.
What we love most about this experience is how it balances storytelling with culinary delights. The guide’s knowledge makes history come alive, and the carefully chosen desserts and drinks give you a taste of Charleston’s culinary soul. The tour’s intimate size—max 10 travelers—means you get more personalized attention and a relaxed environment. However, a possible consideration is the tour’s focus on adults 21+ and the lack of dietary restriction modifications, which might pose challenges for some guests.
This experience is best suited for foodies, history buffs, or anyone wanting to soak in Charleston’s charm with a sweet twist. If you’re looking for a fun, relaxed way to explore and taste your way through the city, this tour could be just right.
Key Points
- Authentic Charleston Experience: Combines historic storytelling with delicious desserts and signature cocktails.
- Expert Guides: Knowledgeable local guides bring Charleston’s past to life.
- Intimate Group: Limited to 10 travelers ensures personalized attention.
- Convenient Location: Starts at East Bay Street and ends near the Charleston City Market.
- Value for Money: Includes drinks, snacks, taxes, and gratuities.
- Adult Only: Designed for guests 21 and over, with no dietary restrictions guarantee.
Planning more time in Charleston? We've covered other experiences worth considering.
Exploring the Details: A Deep Dive into the Sinfully Delicious Dessert Tour

Start with a Walk Through Charleston’s Historic District
We begin at 200 E Bay St, a short walk from downtown hotels and easily accessible via public transportation. The starting point is a vibrant hub full of historic charm, setting the perfect tone for a leisurely exploration. The guide, whose name we wish we knew, greets us warmly and quickly starts unfolding the story of Charleston’s importance as a major port city—symbolized by the impressive 19th-century neoclassical building on East Bay Street, where the tour kicks off.
The 2-Hour Journey: A Perfect Balance of History and Indulgence
This tour isn’t just about tasting; it’s about understanding why Charleston’s culinary traditions are so intertwined with its history. Over the next couple of hours, we meander through the historic streets, alleyways, and squares, with our guide sharing tales of colonists, revolutionaries, pirates, and the city’s high-society. It’s a lively narrative that makes history tangible.
What stands out here is how the guide brings the past alive—highlighting stories of Charleston’s port and its influence on local cuisine. You’ll appreciate the way the guide weaves these narratives with the tasting experience, making each stop both educational and flavorful.
The Sweet Stops and Signature Drinks
The highlight, of course, is the curated selection of Lowcountry desserts. From classic Southern sweets to contemporary treats, each bite is thoughtfully chosen to showcase Charleston’s culinary heritage. You might find that the desserts are rich, decadent, and perfectly paired with signature Southern cocktails—think sweet, spicy, and refreshing flavors that reflect the local spirit.
According to reviews, the delicious food and expert guides are major highlights. One reviewer mentioned, “The guide was knowledgeable and made the whole experience fun, and the desserts were divine.” Another added, “We loved the way the guide explained the history behind each sweet and drink, making the tasting more meaningful.”
- Get Out of Town! Lighthouses, Beaches and Forts Tour
- Charleston: Guided History Walking Tour
- Charleston: Folly Beach Stand Up Paddleboard Dolphin Safari
- Charleston Afternoon Sail – Lux Catamaran w/Seating & Shade
- Charleston: Haunted Pub Crawl for the Broken-Hearted
- Charleston: Historic District Tour With Local Guide
The Atmosphere and Group Dynamics
With a maximum of 10 travelers, the tour maintains a personalized and relaxed atmosphere. This small-group setting allows for more interaction and questions, which many find enhances the experience. Since the tour ends within a mile of the starting point near the Charleston City Market, it’s easy to plan the rest of your afternoon exploring or dining.
Considerations and Practical Tips
A notable point is that this tour is only for ages 21+, due to the alcohol included. If you’re traveling with younger friends or family, this might not be suitable. Plus, there are no accommodations for dietary restrictions, so if you have allergies or special diets, you’ll want to plan accordingly.
The price of $175 includes alcoholic beverages, snacks, taxes, and gratuities, which offers decent value given the experience’s personalized nature and the quality of offerings. Just keep in mind that gratuities for guides are not included—though, in the US, tipping is customary and appreciated.
Why This Tour Works for You

If you’re someone who loves learning about local history while indulging in sweet treats and cocktails, this tour hits the right notes. It’s particularly suited for couples, small groups, or solo travelers who enjoy a more relaxed, intimate setting. It’s also ideal for those who want to experience Charleston’s culinary culture in a fun, social way without committing to a full-day tour.
The Value Proposition

For $175, you’re paying not just for the desserts and drinks, but for an engaging storytelling experience that adds context and meaning to your visit. The tour’s focus on local heritage and authentic flavors makes it a memorable way to spend an afternoon in Charleston. The small group size and knowledgeable guides promise a more personalized experience, which many travelers find enhances the overall value.
The combination of history, food, and drinks, all delivered in a relaxed walking format, offers an experience that’s more than just a tasting—you’re getting a multi-sensory journey through Charleston’s story and flavor.
The Sum Up: Is It Worth It?

This tour is an excellent choice for those wanting to combine Charleston’s history with a sweet and spirited adventure. It offers a relaxed pace, intimate group size, and high-quality offerings that make it stand out among typical city tours. If you’re a foodie, a history enthusiast, or simply looking to enjoy some authentic Southern hospitality, you’ll likely find this tour well worth the price.
However, it’s best suited for adults who appreciate good food, storytelling, and light alcohol. It’s not designed for dietary restrictions or younger travelers, but for those within its target audience, it delivers a memorable taste of Charleston.
FAQ

Is this tour suitable for children or those under 21?
No, this tour is only for guests 21 and over because it includes alcoholic beverages.
How long does the tour last?
The tour lasts approximately 2 hours, making it a manageable activity that won’t take up your whole day.
What is included in the price?
Your ticket includes alcoholic beverages, snacks, soda, taxes, and restaurant gratuities. Gratuities for guides are not included.
Where does the tour start and end?
It starts at 200 E Bay St and ends within a mile radius near Charleston City Market at 188 Meeting St.
Can dietary restrictions be accommodated?
No, the tour does not guarantee modifications for dietary restrictions, so plan accordingly.
How far in advance should I book?
On average, travelers book about 71 days ahead, which suggests the tour can fill up quickly.
What if the weather is bad?
This experience depends on good weather. If canceled due to rain or other weather issues, you’ll be offered a different date or a full refund.
This Sinfully Delicious Dessert Tour offers an enjoyable blend of history, flavors, and local charm—a perfect way to experience Charleston’s sweet side. Whether you’re a first-time visitor or a seasoned local, it’s a delightful addition to your itinerary.
More Tours in Charleston
- USS Yorktown Ghost Tour with Exclusive Night-Time Access
- SMALL group Historic Walking Tours with certified guides
- Discover Charleston! (Small Group Walking Tour – Max 10 Guests)
- Charleston History and Historic Gossip Tour
- Charleston: Magnolia Plantation Entry & Tour with Transport
- Charleston: Striped Pig Distillery Tour and Tasting
More Tour Reviews in Charleston
- USS Yorktown Ghost Tour with Exclusive Night-Time Access
- Charleston Harbor Sunset Cruise
- SMALL group Historic Walking Tours with certified guides
- Discover Charleston! (Small Group Walking Tour – Max 10 Guests)
- Charleston Champagne Figure Drawing Experience with Male Model
- Charleston History and Historic Gossip Tour
More Charleston experiences we've covered
- USS Yorktown Ghost Tour with Exclusive Night-Time Access
- Charleston Harbor Sunset Cruise
- SMALL group Historic Walking Tours with certified guides
- Discover Charleston! (Small Group Walking Tour – Max 10 Guests)
- Charleston Champagne Figure Drawing Experience with Male Model
- Charleston History and Historic Gossip Tour
- Charleston: Spirits & Spirits Haunted Pub Crawl
- Charleston: Magnolia Plantation Entry & Tour with Transport
- Charleston: Striped Pig Distillery Tour and Tasting
- The Best Private History Walking Tour in Charleston!
- Charleston: Dark Side of Charleston 1.5-Hour Walking Tour
- Charleston: Historical Walking Tour with Storytelling
