Boston’s unique blend of history and vibrant bar scene makes it a top city for drink-loving travelers. Its cobblestone streets, colonial taverns, and legendary pubs aren’t just for looking—they’re for tasting. Whether you’re interested in pairing stories of revolution with local brews or exploring haunted haunts with a drink in hand, Boston’s drinking tours offer authentic experiences rooted in the city’s rich past and lively present. These tours aren’t about generic bar-hopping; they’re about stories, local flavors, and memorable moments—all with knowledgeable guides to enhance your experience.
If you’re after a small-group pub crawl with a historical twist, a craft brewery behind-the-scenes tour, or even a spooky ghost-themed pub adventure, Boston has options that will satisfy your curiosity and your palate. For a comprehensive look at the best ways to drink in the city, we’ve compiled a list of the top eight drinking tours based on reviews, uniqueness, and value.
Quick Overview
Our list covers a variety of experiences: from history-focused pub crawls like the Boston Freedom Trail History Pub Crawl Small-Group Tour, to craft brewery explorations such as the Guided Craft Brewery Tour with a Snack, and even haunted pub crawls that combine ghost stories with good drinks. We highlight tours offering small groups, expert guides, and some that include tastings of Boston’s best beers and spirits.
Below, you’ll find the details of each top-rated tour to help you pick the perfect one for your Boston visit.
1. Boston Freedom Trail History Pub Crawl Small-Group Tour
This tour combines Boston’s revolutionary history with its thriving pub scene. It starts right outside Faneuil Hall at the Samuel Adams statue, and from there, your guide takes you along The Freedom Trail to visit some of Boston’s most iconic and unique pubs. What’s special here is the option to have a Happy Hour experience with four beers or ciders included, or to go dry and purchase drinks as you go.
With the small-group format—guaranteed to be no larger than 16—you’ll get a more personal experience. Tour guides like Julia and Hallie are praised for their knowledge and energy, sharing stories as you hop between historic bars within a few blocks. Guests particularly appreciate the mix of entertainment and education, along with the chance to try recommended local brews. The tour’s 2-hour 15-minute duration is perfect for those wanting a lively but not overwhelming experience.
Bottom Line: This tour suits history buffs who enjoy a lively atmosphere and casual drinking, with reviews consistently rating it a perfect 5-star experience.
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2. Boston: History Pub Crawl Tour Along the Freedom Trail
At number 2, this History Pub Crawl offers a blend of local craft beers and historical tales. Led by expert guides, you’ll explore historic taverns and hidden bars that line the Freedom Trail, with a focus on Boston’s influence on American history, including the Boston Massacre and revolutionary events.
Priced at $59, this 2-hour tour is praised for its engaging storytelling and insider perspective. Guests often mention the friendly, knowledgeable guides like Claudia and Anna, who make the history come alive while keeping the mood light with tastings of local brews. The tour covers exclusive Boston beers, giving you a taste of the city’s brewing scene alongside stories of its turbulent past.
It’s a flexible tour—many options to customize—making it ideal for those who want a mix of history and craft beer. Expect to visit some of Boston’s iconic historic pubs, with plenty of time to mingle and enjoy the drinks.
Bottom Line: Best for history lovers who want a genuine local experience with craft beers, all within a lively, interactive format.
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3. Boston: Freedom Trail History Tour and Brewery Taste
For about $79, the Freedom Trail History Tour and Brewery Taste offers a full immersion into Boston’s revolutionary past plus a vibrant brewery experience. This 2.5-hour tour takes you through 11 of the 16 official Freedom Trail landmarks, such as Faneuil Hall, the Boston Massacre site, and Old South Meeting House.
What makes this tour standout is the combination of walking history and a locally-sourced craft beer tasting at a brewery. After exploring Boston’s historical sites with an expert guide, you’ll enjoy a delicious lunch featuring Boston specialties like lobster rolls and clam chowder, paired with beers from a local brewery. Guests rave about guide Nick’s storytelling and the inclusion of Boston’s Revolutionary history along with modern craft beers.
While slightly longer, the tour is well worth it for anyone who wants a comprehensive historic experience with a culinary twist. The small group size means you get plenty of personalized attention.
Bottom Line: Suited for those eager to connect Boston’s colonial past with its current craft beer scene, and happy to walk a bit more for a richer experience.
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4. Boston: Guided Craft Brewery Tour with a Snack
If exploring Boston’s craft beer scene is your main goal, this Guided Craft Brewery Tour hits the mark. For $105, you’ll visit three local breweries or cider houses, with VIP behind-the-scenes access at each location. Your expert guide, Adrian or Raj, takes you through the brewing process, highlighting Boston’s innovative craft scene.
Participants enjoy sampling up to 12 different beers or ciders, with a tasty snack to help soak up the suds. The tour lasts 3.5 hours, and transportation is included, making for a relaxed, hassle-free experience. Guests praise the friendly guides and the chance to see the inner workings of Boston’s breweries, which isn’t always possible on larger tours.
This tour is perfect for beer enthusiasts, foodies, or anyone wanting a behind-the-scenes look at Boston’s craft industry. The small-group setting ensures a personalized experience, and the mix of tastings and insights makes it good value, especially compared to brewery tastings alone.
Bottom Line: A solid choice for craft beer lovers who want VIP access and a relaxed pace without sacrificing depth of experience.
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5. Pizza Beer and Paul Revere Tour
For a laid-back, local favorite experience, this Pizza, Beer, and Paul Revere Tour offers a casual way to explore Boston’s North End. Guided by Jimbo the Tye Dyed Tour Guide, this 2-hour tour focuses on authentic pizza slices, hidden bars, and the history of Paul Revere’s stomping grounds.
Jimbo emphasizes a friendly, conversational style, making it feel like hanging out with an old friend. You’ll visit small bakeries, local bars, and historic alleyways that most larger tours skip. The tour combines informal storytelling with tasting some of Boston’s best pizza and a cold beer, making it ideal for travelers wanting a relaxed, authentic experience. The reviews highlight Jimbo’s knowledge and personable style, with many calling it “a great way to start your trip.”
This tour is excellent for foodies, casual explorers, or those interested in local neighborhoods rather than just history. It’s affordable and quick, perfect if you want a taste of North End life without a long commitment.
Bottom Line: Best suited for travelers who want an informal, fun evening with good pizza, beer, and local flavor.
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6. Boston: Boos and Brews Haunted Pub Crawl
Dark, spooky, and fun—this Haunted Pub Crawl takes you through Boston’s haunted bars and historic sites for 2 hours of ghostly tales and drinks. For just $29, you’ll visit four pubs and five significant haunted locations, including the Omni Parker House and the Granary Burying Ground.
Guides like Paxtin or Julia share stories of spectral sightings, blood-stained streets, and ghostly apparitions tied to Boston’s history—like the ghost of John F. Kennedy or the martyr Mary Dyer. Guests praise the entertaining storytelling and the chance to explore offbeat historic sites while enjoying drinks. The tour provides a mix of history, ghost stories, and local taverns, making it ideal for those who enjoy a spooky twist on their night out.
While shorter, the tour’s focus on haunted legends and small-group intimacy creates an engaging atmosphere. It’s perfect for history and ghost enthusiasts wanting a lighthearted but spine-tingling experience.
Bottom Line: Great for travelers interested in ghost stories and haunted locations, with enough drinks to keep fears at bay.
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7. Boston Ghosts Boos and Brews Haunted Pub Crawl
If you want a slightly more spooky but less intense experience, this Ghosts, Boos, and Brews is a solid pick. It covers four Boston pubs with haunted histories, including tales of restless spirits and hidden specters. For $36, this 2-hour tour emphasizes the city’s ghostly lore alongside local pubs like the 21st Amendment and the Last Hurrah.
Guides like Max or Nicole are noted for their engaging storytelling, sharing spooky stories based on Boston’s architecture and old cemeteries. Guests enjoy the personalized attention on small-group tours, and many reviewers mention the entertaining mix of humor and history. The tour is ideal for those who appreciate haunted legends with a side of local craft beer.
While not as intense as the previous haunted options, it offers plenty of chilling tales and lively pub stops. It’s a good pick if you want a balance of ghost stories and relaxed drinking.
Bottom Line: Perfect for those intrigued by Boston’s spooky side who want a fun, not frightful, night out.
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8. Boston Haunted Pub Crawl
Rounding out the list, this Haunted Pub Crawl is focused on dark stories and eerie locations. For $29.99, you’ll visit several historic pubs and haunted sites, including the Green Dragon Tavern and Ned Devine’s. Guides recount tales of blood-stained streets, Revolutionary War ghosts, and spectral sightings in Boston’s oldest neighborhoods.
The tour lasts about 2 hours and offers a mix of history, local legends, and a few drinks. Reviewers appreciate the well-told stories and the chance to explore Boston’s darker side while enjoying a relaxed atmosphere. It’s suitable for history fans and those interested in ghostly legends, especially if you’re on a budget.
Given its affordability and focus, this tour is a good option for casual guests wanting spooky stories plus a few drinks without a long commitment.
Bottom Line: Best for budget-conscious travelers who want a spooky night of stories and drinks in Boston’s historic pubs.
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How to Choose the Right Drinking Tour in Boston
When picking your ideal drinking tour, consider your interests—are you after history, craft beers, haunted stories, or a mix? For history buffs who want a lively atmosphere, the Boston Freedom Trail History Pub Crawl Small-Group Tour offers a great combination of storytelling and local pubs. If you seek craft beer knowledge and behind-the-scenes access, the Guided Craft Brewery Tour with a Snack is ideal. Budget travelers might prefer the Boston Haunted Pub Crawl, which offers spooky fun at a lower price point.
Think about group size—smaller groups (under 10-16 guests) tend to be more engaging and personalized, while larger tours can be more social. Also, check duration—some tours are quick 2-hour outings, while others like the brewery tour can extend over 3.5 hours. Book early, especially during peak seasons, to secure your spot.
Lastly, consider your walking ability—some tours involve significant walking, while others include transportation or are shorter walks. Match your choice with your preferred pace and interests for a memorable Boston drinking experience.
In Summary
Boston offers a fantastic array of drinking experiences, from historic pub crawls along the Freedom Trail to craft brewery tours and haunted pub adventures. For a rich mix of history and local flavor, the Freedom Trail pub crawl and history + brewery tours stand out. If you’re after something more casual and fun, the Pizza, Beer, and Revere Tour or haunted tours like Boos and Brews present a relaxed way to enjoy Boston’s spirit—both literal and figurative.
No matter your style, booking in advance is recommended—these tours are popular, and early planning ensures you won’t miss out on a memorable night of history, local brews, and ghostly tales. Cheers to exploring Boston’s diverse drinking scene!