Boston’s drinking tours blend history and libations in uniquely meaningful ways. The city’s classic pub crawls along the Freedom Trail stand out for their expert storytelling and historic tavern stops. Local craft brewery tours, particularly in up-and-coming neighborhoods like Fort Point and Charlestown, showcase Boston’s innovative beer scene with generous tastings and behind-the-scenes access. For something different, evening ghost-and-pub tours combine spine-tingling stories with stops at centuries-old watering holes.

I’m especially fond of the Freedom Trail Pub Tour for its perfect mix of Revolutionary War history and traditional New England taverns, while the Craft Brewery Adventures tour wins points for its intimate glimpses into Boston’s best microbreweries.

Let’s explore the top drinking tours in Boston.

Key Points

  • The Boston Small-Group Freedom Trail History Tour Pub Crawl combines historical sightseeing with visits to local pubs, offering a unique drinking experience.
  • The Boston Signature Guided Brewery Tour provides VIP access to award-winning breweries, allowing participants to sample 12 beer varieties and enjoy a pretzel snack.
  • The Boston: Boos and Brews Haunted Pub Crawl takes visitors to 9 haunted sites, including 4 pubs, while sharing local ghost stories and history.
  • The Guided Craft Brewery Tour offers a 3.5-hour experience featuring 12 craft beer samples at 3 breweries or cider houses, with expert guidance.
  • The Boston Haunted Pub Crawl explores haunted pubs with engaging storytelling, providing a unique and social drinking experience for participants 21 and older.

Boston Small-Group Freedom Trail History Tour Pub Crawl

Boston Small-Group Freedom Trail History Tour Pub Crawl

For those seeking to explore Boston’s historic sites and sample its vibrant drinking culture, the Boston Small-Group Freedom Trail History Tour Pub Crawl offers an engaging and immersive experience.

Rated 4.9 out of 5 based on 781 reviews, this small-group tour takes participants on a walking journey along the renowned Freedom Trail, with stops at historic pubs.

Guests can opt for the “Happy Hour” package, which includes four draft beers, or the “Dry Run” option to purchase drinks individually.

Accessible to wheelchair users and suitable for those 21 and older, the tour promises an entertaining blend of history and libations, led by knowledgeable local guides.

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Boston: History Pub Crawl Tour Along the Freedom Trail

Boston: History Pub Crawl Tour Along the Freedom Trail

Immersing visitors in Boston’s storied past and vibrant drinking culture, the History Pub Crawl Tour along the Freedom Trail offers an engaging exploration of the city’s iconic landmarks and hidden watering holes.

Over the course of two hours, participants can choose between a Happy Hour or Dry Run option, tasting exclusive local brews while learning about beer’s influence on American history.

Led by knowledgeable guides, the tour traverses the Freedom Trail, uncovering untold stories from Boston’s colonial and revolutionary eras.

With a 4.8/5 overall rating and strong praise for the engaging experiences, this tour provides an unforgettable way to discover Boston’s rich heritage and lively bar scene.

Read our full review: Boston: History Pub Crawl Tour Along the Freedom Trail Review
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Boston Signature Guided Brewery Tour

Boston Signature Guided Brewery Tour

Setting out on a delightful journey through Boston’s burgeoning beer scene, the Boston Signature Guided Brewery Tour offers an immersive exploration of the city’s award-winning craft breweries.

Featuring VIP access to iconic breweries, up to 12 beer samples, and a pretzel snack, this half-day excursion promises an exceptional experience.

Led by a knowledgeable local guide, the tour provides round-trip transportation and hotel pick-up and drop-off for added convenience.

With a maximum of 14 travelers per tour, visitors can enjoy a personalized and intimate experience.

Catering to adults 21 and older, the tour isn’t recommended for pregnant individuals and requires a valid ID.

Vegetarian options are available upon request, and the tour operates in all weather conditions.

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Boston: Boos and Brews Haunted Pub Crawl

Boston: Boos and Brews Haunted Pub Crawl

Explore Boston’s haunted past and sample local brews on the Boston: Boos and Brews Haunted Pub Crawl. This 2-hour tour takes visitors to 9 historic, haunted sites, including 4 pubs.

Highlights include the 21st Amendment pub, rumored to be haunted by the ghost of John F. Kennedy, and the Omni Parker House Hotel, where a haunting is said to occur in Room 303.

Led by knowledgeable and engaging guides, the tour shares authentic local ghost stories and credible history.

With an overall rating of 4/5 from 52 reviews, the tour is suitable for those 21 and over, but not for those with mobility issues. Comfortable shoes and a valid ID are recommended.

Read our full review: Boston: Boos and Brews Haunted Pub Crawl Review
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Boston Ghosts Boos and Brews Haunted Pub Crawl

Boston Ghosts Boos and Brews Haunted Pub Crawl

The Boston Ghosts Boos and Brews Haunted Pub Crawl takes visitors on a captivating journey through the city’s haunted past, blending historical accounts with the opportunity to sample local libations.

This small-group tour offers an immersive experience, with professional guides sharing intensely researched true stories of Boston’s ghostly haunts. Participants visit four local bars, learning about the city’s architecture and spooky history along the way.

The tour provides personal attention and is accessible to a range of travelers, though a moderate fitness level is required. Feedback highlights the entertaining guides and enjoyable experiences, despite some concerns about pacing and value.

Read our full review: Boston Ghosts Boos and Brews Haunted Pub Crawl Review
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Boston: Guided Craft Brewery Tour With a Snack

Boston: Guided Craft Brewery Tour With a Snack

On this guided craft brewery tour, visitors explore Boston’s thriving beverage scene.

Over 3.5 hours, up to 12 craft beer samples are provided at 3 local breweries or cider houses. The tour includes round-trip transportation, a snack, and an expert beer guide. Guests gain VIP access to brewery operations and learn local history.

A variety of beer styles, from pilsners to stouts, are sampled. The tour accommodates vegetarians, and comfortable shoes are recommended.

With a 4.9/5 rating based on 21 reviews, the tour is praised for its knowledgeable and entertaining guides, such as Raj and Adrian, as well as the overall service and organization.

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Boston Haunted Pub Crawl

Boston Haunted Pub Crawl

Embarking on the Boston Haunted Pub Crawl, visitors enjoy the city’s storied past. For $29.99 per person, this 3.8-rated tour offers a unique blend of history and nightlife.

Led by knowledgeable guides like Nicole, Liberty, and Max, guests explore Boston’s haunted pubs while learning about spooky local tales. The tour takes participants to various establishments, including the beloved Green Dragon and Bell in Hand Tavern.

While some reviewers noted difficulty hearing the guide due to noise, the social atmosphere and engaging storytelling were widely praised.

Despite mixed feedback on the connection between the pubs and ghost stories, many travelers highly recommend this tour for its distinctive experience.

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Boston: Haunted Pub Crawl of Historic Pubs and Taverns

Boston: Haunted Pub Crawl of Historic Pubs and Taverns

What better way to explore Boston’s haunted past than by embarking on a Haunted Pub Crawl of the city’s historic pubs and taverns?

This 2-hour activity takes you on an adventure through the streets frequented by American Patriots, where you’ll hear tales of the Founding Fathers and Boston’s spooky history.

Led by knowledgeable guides, the tour visits haunted establishments like the notorious Union Oyster Pub.

Priced at $29.99 per person, the tour accommodates up to 9 participants and is wheelchair accessible.

While individuals under 21 aren’t allowed, the experience includes drinks, tips, and an overall rating of 4.5/5 from 87 reviews praising the engaging stories.

Read our full review: Boston: Haunted Pub Crawl of Historic Pubs and Taverns Review
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Sum Up

Boston offers a variety of engaging drinking tours for visitors. From historical pub crawls along the Freedom Trail to guided brewery tours, there’s something for every taste. These tours provide a unique way to explore the city’s rich history and thriving craft beer scene. Whether you’re a history buff or a beer enthusiast, Boston’s drinking tours promise an unforgettable experience.