Charleston’s charm isn’t only in its cobblestone streets and antebellum houses; it’s also in its lively drinking scene. The city’s rich history, from Prohibition-era speakeasies to time-honored breweries, makes it a fantastic place for drinking tours. Whether you’re after a walking history and bar experience, a scenic winery and brewery tour, or a ghostly pub crawl, Charleston offers a variety of ways to enjoy its adult beverages with a side of local stories. These tours are perfect for those who want to pair their love of history and architecture with some well-earned drinks.
Unlike many other cities, Charleston’s drinking tours emphasize storytelling and unique local flavors. From small-group pub crawls to limo-driven tastings on Wadmalaw Island, there’s an experience for every taste and schedule. Just be prepared for some lively nights and memorable moments.
1. Charleston: Walking History and Bar Tour
At number 1 on our list, the Charleston: Walking History and Bar Tour hits the mark for combining local history with crafty bar stops. This 2-hour experience explores the French Quarter, one of Charleston’s most iconic neighborhoods, with visits to two popular bars. Led by a licensed guide and historic commissioner, the tour dives into Charleston’s past, including secret stories only locals know. You’ll sample drinks crafted by local breweries and distilleries, making it a perfect blend of education and relaxation. Guests consistently praise guide Captain Bryan for his deep knowledge and energetic storytelling, with many mentioning how the tour offered more than just drinks — it was a history lesson with a fun twist.
This tour is especially good for travelers who want to learn about Charleston’s hidden stories while enjoying a couple of refreshing drinks. The intimate small-group setting ensures personalized attention, and the moderate price point makes it accessible. The only potential downside is the limited duration—some might wish it lasted longer—but it’s a solid choice for a quick, memorable introduction to Charleston’s drink and history scene.
Bottom Line: A lively, engaging tour perfect for those who enjoy history with their cocktails, especially if you want local insights from a passionate guide.
2. Charleston Winery, Brewery & Sightseeing Tour
Up next, the Charleston Winery, Brewery & Sightseeing Tour offers a full-day adventure on Wadmalaw Island. For around $155, you’ll ride in a limo party bus with your own chauffeur, visiting a famous 500-year-old Angel Oak Tree, and exploring the Deepwater Vineyard for tastings. The tour continues with a local brewery stop where the first round is on the guide, plus optional sightseeing at the Charleston City Market, Battery, White Point Gardens, and Rainbow Row. The itinerary combines scenic views, historical landmarks, and beverage sampling, making it ideal for those who want a broader experience.
Guests rave about the personal touches, with guides Mitchell and Connie praised for their friendliness and knowledge. The tour’s length—about 6 hours—means you’ll get a good mix of wine, beer, and sightseeing, all with the convenience of door-to-door service. It’s suitable for travelers who love a multi-faceted day with plenty of tastings and chances to explore the Lowcountry’s natural beauty.
Bottom Line: Ideal for those who want a luxurious, all-in-one tour with scenic stops, tastings, and tailored service, perfect for a special occasion or a comprehensive day out.
3. Speakeasy Sagas – Charleston Prohibition Pub Crawl
Number 3 is the Speakeasy Sagas – Charleston Prohibition Pub Crawl. This 2-hour tour offers a lively dive into Charleston’s Prohibition history, visiting historic landmarks like the U.S. Customs House and Old Exchange & Provost Dungeon. Led by guides who bring Charleston’s 1920s speakeasy culture to life, you’ll hop into some of the best local bars and sample drinks while hearing stories of bootlegging, secret deals, and hot spots of the era.
Rated highly for its historical storytelling, this tour is best suited for those with a curiosity about America’s alcohol ban and who enjoy a social atmosphere. The small group (up to 15) ensures an engaging experience. Guests mention the guide’s passion and knowledge, making the history just as enjoyable as the drinks.
Bottom Line: A fun, educational pub crawl that combines liquid history with Charleston’s atmospheric bars, perfect for history buffs and social drinkers alike.
4. Day Drinking Tour
At number 4, the Day Drinking Tour is a 4-hour jaunt through Charleston’s craft beer scene. This private group experience costs around $99 per person but offers visits to three top breweries—each with four beer pours—and insights into the brewing process and local beer culture. Traveling by comfortable coach, you’ll avoid the hassle of driving while sampling a dozen beers. Guests often comment on the guide’s entertainment and rich history lessons, making it more than just a tasting.
This tour is perfect if you’re into craft beer and want a relaxed, social experience with friends or family. The highlight is the variety—12 beers in total—and the opportunity to learn about Charleston’s brewing history directly from your guide. Some may find it a bit condensed if you want a more leisurely pace, but overall, it offers excellent value.
Bottom Line: A great choice for beer lovers seeking an easy-going, guided tasting tour that covers multiple breweries with plenty of variety.
5. Charleston: Harbor Bar Pedal Boat Party Cruise
Number 5 features the Harbor Bar Pedal Boat Party Cruise. This 1.5-hour cruise combines scenic views of Charleston’s coastline with plenty of fun. With 12 pedaling stations and room to dance, it’s as much a party as a sightseeing trip. You can bring your own beverages, making it a flexible choice for groups celebrating anything from birthdays to bachelorette parties.
Guests rave about the captain’s friendliness and the lively atmosphere, with many mentioning how much fun they had dancing and cruising the river. The boat departs from Ripley Light Marina, offering a memorable way to enjoy Charleston’s waterfront.
Bottom Line: A fantastic, energetic cruise for groups wanting a mix of sightseeing and socializing, especially if you enjoy music and dancing with friends.
6. Charleston: Speakeasy Sagas Prohibition Pub Crawl
Number 6 is similar in theme but slightly longer and more detailed than its predecessor. The Charleston: Speakeasy Sagas Prohibition Pub Crawl takes you through historic bars, uncovering Charleston’s Prohibition-era secrets. Led by guides like Jamie and Josh, you’ll explore landmarks such as St. Philip’s Church and the Old Exchange, all while tasting some of Charleston’s best cocktails.
Guests appreciate the storytelling and the personal touch guides bring. It’s well-suited for travelers interested in deeper liquor lore and who enjoy a paced, social experience. The tour’s combination of history, drinks, and lively atmosphere makes it a top pick for those who want a comprehensive pub crawl.
Bottom Line: Excellent for history enthusiasts who want to enjoy Charleston’s cocktail culture with a structured yet relaxed approach.
7. Charleston: Craft Beer and Cocktails Guided Tour
Number 7 offers a 2-hour Craft Beer and Cocktails Guided Tour, showcasing Charleston’s nightlife scene. Starting at 54 N Market St, the tour visits three carefully selected venues—ranging from cozy pubs to hidden speakeasies—each with its own unique vibe. Expect a mix of local stories, delicious drinks, and insider tips that make each stop special.
Goers love how guides like Jackson combine history and fun, making the experience both educational and entertaining. It’s a perfect option for those looking for a shorter, social adventure that highlights the city’s bar scene. The reviews mention the quality of drinks and the personable guides, making it a popular pick.
Bottom Line: A quick, lively tour ideal for those wanting to explore Charleston’s bar scene, with a focus on craft drinks and local lore.
8. Charleston: Boo-Hag and Brews Haunted Bar Hop
Number 8 is the Boo-Hag and Brews Haunted Bar Hop. Over 2 hours, this tour blends ghost stories with bar hopping in the French Quarter. You’ll hear tales of ghosts, spirits, and local legends while visiting some of Charleston’s most haunted pubs and bars, like the famous Angel Oak.
Tour guides like Captain Bryan are praised for their energy and knowledge, making it a spooky yet fun experience. It’s perfect for those who enjoy haunted history and want to combine drinks with storytelling. The tour’s small size ensures an engaging, personalized experience.
Bottom Line: A great pick for lovers of ghost stories and haunted Charleston, with plenty of drinks along the way.
Number 9 is the Bay Street Bastards Pub Crawl. This small-group, true crime-themed crawl explores Charleston’s criminal past over 2 hours. Led by guides like Abby and Alex, you’ll visit four bars and hear tales of notorious criminals and Charleston’s dark deeds.
Guests appreciate the personalized stories and the mix of history and drinks. The tour is especially good for those interested in true crime stories and want a more intimate experience. Drinks are paid for separately, so budget accordingly.
Bottom Line: Perfect for those who enjoy history with a dark twist, and want a small, focused group for a more personal adventure.
10. Charleston Brewery District Cruise (Public Tour)
Number 10, the Charleston Brewery District Cruise, combines a boat cruise with visits to four breweries. Starting at the Charleston Visitors Center, the 4-hour tour includes unlimited stops at Holy City Brewing, Revelry Brewing, Palmetto Brewing, and more, with drinks included.
Guests love the scenic views of the city, the guided commentary, and the chance to sample local beers without worrying about driving. The tour is ideal for beer enthusiasts who want a scenic, social experience that also includes photo opportunities of Charleston’s famous spots.
Bottom Line: A perfect choice for beer lovers who want a combination of scenic cruise and brewery hopping with included drinks.
11. Charleston: Spirits & Spirits (Haunted Pub Crawl)
Number 11 offers the Spirits & Spirits Haunted Pub Crawl, an atmospheric 2-hour tour that explores Charleston’s paranormal side. You’ll visit haunted pubs while listening to ghostly tales of vengeful spirits and murderous legends. Guides are fully licensed and bring Charleston’s spooky stories to life.
Ideal for fans of ghost stories and haunted history, this tour’s small size ensures an intimate atmosphere. The drinks are purchased separately, so plan accordingly. Reviewers note the enthralling storytelling and darkly fun vibe.
Bottom Line: A spooky, entertaining tour for those intrigued by Charleston’s ghostly legends combined with a drink or two.
12. Charleston’s Spirits & Spirits Haunted Pub Crawl
Number 12 is the Spirits & Spirits Haunted Pub Crawl. Covering 2 hours, it visits some of Charleston’s most haunted spots like the Blind Tiger Pub and Bar Vauté. The tour combines ghost stories with local libations, offering a fun mix of history and drinks.
Guests highlight the storytelling and the chance to explore haunted locations. It’s best suited for those who want a frightening twist on their pub experiences. Price point is budget-friendly at $27 per person.
Bottom Line: A haunted pub crawl experience perfect for those who enjoy spooky tales alongside their drinks.
13. Charleston Bachelorette Bar Crawl
Number 13 offers the Charleston Bachelorette Bar Crawl, a lively 2-hour tour designed for celebrating. It visits handpicked venues like Henry’s, The Griffon, and The Blind Tiger, combining Southern charm with modern craft beers. The tour includes fun activities like Bar Trivia to test your Charleston knowledge and add some friendly competition.
Rated a perfect 5/5, the tour is praised for its personalized service and lively atmosphere. It’s ideal for groups celebrating special occasions, offering a relaxed yet festive environment.
Bottom Line: The perfect bachelorette or celebration tour, blending history, fun, and some friendly rivalry.
14. Private Luxury Chauffeured Transportation to & from Distilleries, Breweries
For those seeking ultimate comfort and flexibility, the Private Luxury Chauffeured Transportation is a 6-hour personalized tour. Costing around $875 per person, it includes visits to Angel Oak, Deep Water Vineyards, and Firefly Distillery, with customized stops. Your chauffeur handles the driving, allowing you to focus on tasting and exploring.
Guests appreciate the tailored itinerary and luxury service, making it ideal for special occasions or groups wanting an exclusive experience. It’s the priciest option but offers the most flexibility and comfort.
Bottom Line: Top-tier choice for those who want a private, customizable day with distillery and vineyard visits in style.
15. Charleston: Spirits & Spirits Haunted Pub Crawl
Rounding out the list, the Spirits & Spirits Haunted Pub Crawl at $29 per person is a budget-friendly way to explore Charleston’s haunted bars over 2 hours. This tour is perfect for those who want ghost stories mixed with a few drinks. Led by enthusiastic guides, it combines history and spooky tales with visits to popular pubs like the Blind Tiger.
It’s a good option for budget-conscious travelers who want a bit of everything—history, haunted tales, and drinks—without a hefty price tag.
Bottom Line: An affordable, fun haunted pub crawl that combines Charleston’s ghost lore with good drinks.
How to Choose Your Perfect Drinking Tour
When deciding which tour to book, consider your interests and schedule. If you’re more into history and local stories, the Walking History and Bar Tour or Prohibition Pub Crawl are great options. For craft beer fans, the Day Drinking Tour or the Brewery District Cruise offer diverse tastings and scenic views. If you’re into ghost stories and haunted locations, Tours like Boo-Hag and Brews or Spirits & Spirits deliver spooky fun. Budget considerations matter too; many tours are very affordable, while private options provide more customization for special occasions.
Booking in advance is recommended, especially for popular tours, and some like the Private Chauffeured Experience sell out early. Think about how much time you want to dedicate—half-day or just a quick evening—and choose accordingly.
To sum up, Charleston offers a wide range of drinking tours that showcase its history, craft beer scene, and haunted legends. For the history lover, the Walking Tour provides local stories and delicious drinks, while the Winery and Brewery Tour gives a full-day scenic experience. Ghost enthusiasts will find the Haunted Pub Crawl especially thrilling. Whatever your preference, booking early guarantees a spot in these popular experiences.