The Top 15 Drinking Tours In Boston

Boston is a city that takes its drinking seriously, blending history, craft beer, and lively tavern culture into memorable experiences. Its compact downtown, historic neighborhoods, and thriving brewery scene make it an ideal place for drinking tours.

Whether you’re a history enthusiast who wants to sip in the same taverns as Paul Revere, a craft beer lover eager to see local breweries behind the scenes, or a fan of spooky stories, Boston has a tour for you.

One of our favorites is the Boston Freedom Trail History Pub Crawl Small-Group Tour, which combines history and four different beers, making it both educational and fun.

Another standout is the Signature Boston Guided Brewery Tour with snack, which offers an in-depth look at Boston’s craft beer scene with visits to notable breweries like Night Shift and Dorchester Brewing. For those who love a spooky twist, the Haunted Pub Crawl of Boston combines ghost stories with historic drinking spots.

Whatever your preference, Boston’s drinking tours provide authentic local flavor, lively stories, and a great way to experience the city’s unique character. Below, we explore each tour in detail to help you pick the one that fits your style.

1. Boston Freedom Trail History Pub Crawl Small-Group Tour

At number one, this small-group pub crawl stands out for its perfect pairing of history and beer. Starting outside Faneuil Hall at the Samuel Adams statue, your guide leads you along the Freedom Trail, visiting historic pubs within walking distance of each other. The Happy Hour option includes four draught beers or ciders, making it ideal for those who want a relaxed yet immersive experience.

What makes this tour special is the focus on America’s early years, with stories intertwined with visits to iconic pubs. Rated 5/5 from over 850 reviews, guests love the knowledgeable guides and the intimate setting.

The tour lasts about 2 hours 15 minutes, which is just enough to enjoy a few drinks and learn about Boston’s revolutionary past. It’s perfect for history buffs who want a lively way to experience local taverns without feeling rushed.

Bottom Line: This tour offers a balanced mix of history and fun, especially for those wanting a small-group feel with a tasty beer or cider in hand.

2. Signature Boston Guided Brewery Tour with Snack

For craft beer lovers, the Signature Boston Guided Brewery Tour provides an in-depth look at Boston’s vibrant brewing scene. Over three hours, you’ll visit breweries like Night Shift and Dorchester Brewing Company, with behind-the-scenes access and expert guides explaining the brewing process. It’s a great choice if you want to see how local craft beers are made.

Guests consistently praise the tour for its knowledgeable guides and the opportunity to sample a wide variety of beers and ciders—up to 12 in total. Including round-trip transportation from downtown Boston, it’s convenient and comprehensive.

At $119, it may seem pricey, but the quality of breweries visited and the VIP experience make it worth considering. This tour is suitable for those who want a more immersive craft beer adventure with snacks to complement the tastings.

Bottom Line: If craft beer is your thing, this tour’s behind-the-scenes access and local brewery visits deliver excellent value.

3. Boston: History Pub Crawl Tour Along the Freedom Trail

This history-rich pub crawl marries local history with craft beer in a flexible, customizable format. Starting at the historic Faneuil Hall, your guide leads you through hidden taverns and iconic bars along the Freedom Trail. You’ll taste exclusive local brews while hearing stories about events like the Boston Massacre.

Rated 4.9/5, guests love the insider perspective and the chance to choose different options. It lasts about 2 hours, making it a perfect quick yet immersive experience. It’s ideal for travelers who want to combine historical insights with local drinking spots, all with a knowledgeable guide making the stories come alive.

Bottom Line: A flexible, history-focused pub crawl that offers a personal touch combined with authentic Boston taverns.

4. Boston Historic Pubs with Food & Drink, Ferry & Walking Tour

For those who want a full sensory experience, this half-day tour combines historic pubs, food, and a scenic ferry ride. You’ll explore neighborhoods like the North End, Charlestown, and Beacon Hill, visiting historic taverns and sampling local snacks along the way.

A highlight is the ferry ride across Boston Harbor, providing stunning views of the city skyline. The tour lasts around 3.5 hours and has a small-group setting for a more personal experience. Guests rave about the authentic tavern snacks and the chance to enjoy Boston’s historic streets with a cold drink in hand.

Bottom Line: Ideal for those who want a leisurely, full-day experience with food, drinks, and scenic views.

5. Boston: Historic Pubs with Food & Drink, Ferry & Walking Tour

This historic pub tour takes you inside some of Boston’s oldest taverns, like the Warren Tavern, where George Washington supposedly stopped. It combines walking, ferry rides, and drinks, making it perfect for history and food lovers.

During the 3.5-hour tour, you’ll enjoy a drink and appetizer at historic pubs, culminating with a ferry trip across Boston Harbor. Reviews highlight guides who share engaging stories and the opportunity to drink in the same venues as Revolutionary figures. This tour is best suited for those wanting a mix of history, food, and scenic Boston.

Bottom Line: A rich experience for those who love history, local food, and scenic boat rides.

6. 2 Hour Historic Pub Crawl in Boston

If you’re after a quick, lively introduction, this 2-hour pub crawl hits the top historic pubs like Green Dragon and The Bell in Hand. Rated 5/5, it’s perfect for tight schedules but still offers plenty of history and beer.

Guests praise the knowledgeable guides and the relaxed pace that allows for enjoying a few pints while learning about Boston’s brewing history. At only $35, it’s one of the most affordable options without sacrificing authenticity or fun. It’s best for travelers who want a taste of Boston’s pub scene in a short time.

Bottom Line: Great value for a quick, entertaining introduction to Boston’s historic pubs.

7. Boston: Haunted Pub Crawl of Historic Pubs and Taverns

For a spooky twist, try this haunted pub crawl, which blends ghost stories with visits to historic taverns. It’s rated 4.6/5 and lasts 2 hours, with tales of spirits from Boston’s revolutionary past and haunted locations like the Miller Plaza Pavilion.

Guests love the engaging storytelling and the chance to drink in places haunted by history. Whether you believe in ghosts or not, it’s a fun way to experience Boston’s darker side. This tour is suited for those interested in paranormal stories and historic pubs with a spooky reputation.

Bottom Line: A lively, entertaining tour for those who enjoy ghost stories and historic drinks.

8. Boston: Guided Craft Brewery Tour with a Snack

Beer aficionados should consider this guided craft brewery tour, which takes you behind the scenes at three local breweries or cider houses. Over approximately 3.5 hours, you’ll sample up to 12 beers and enjoy a tasty snack.

Guests note the VIP access and expert guidance as highlights, with guides sharing insights about each brewery’s history and brewing process. The included transportation makes it easy to hop from one brewery to the next. It’s perfect for those who want an up-close view of Boston’s craft scene and enjoy tasting a variety of local brews.

Bottom Line: An excellent choice for craft beer enthusiasts seeking in-depth access and a substantial number of tastings.

9. Pizza Beer and Paul Revere Tour

For a fun, casual experience, the Pizza, Beer, and Paul Revere Tour combines pizza, beer, and historic sights in Boston’s North End. Guided by “Jimbo,” the colorful tour guide, you’ll explore cobblestone streets, see Paul Revere’s house, and enjoy two slices of pizza with a pint.

Guests rave about the informal atmosphere and “authentic” local spots. It’s a great option for travelers who want a social, relaxed way to experience Boston’s history and food without the formality of larger tours. The tour lasts 2 hours and is best suited for those wanting a laid-back, friendly vibe.

Bottom Line: Perfect for casual travelers seeking good food, drinks, and local stories.

10. Boston Haunted Pub Crawl

This haunted pub crawl offers a spirited mix of ghost stories and drinks, visiting haunted bars where Boston’s spooky past comes alive. It lasts about 2 hours and costs around $29.99.

Guides share tales of ghostly encounters at places like 60 Congress Street and Ned Devine’s, blending revolutionary history with supernatural stories. It’s a fun choice for those wanting a lighter, spooky experience combined with local drinks. Reviewers mention the engaging stories and the lively atmosphere.

Bottom Line: A budget-friendly, spooky way to drink and learn about Boston’s ghostly legends.

11. Boston: Boos and Brews Haunted Pub Crawl

For fans of ghost stories with a historical twist, the Boos and Brews Haunted Pub Crawl offers a small-group experience exploring Boston’s haunted pubs and alleys. Rated 4/5, it visits four local bars with tales of spirits and scandal from Boston’s past.

Guests enjoy the personalized attention and the chance to taste drinks in haunted venues. It’s suitable for those who want a spooky story with their pint, especially in historic settings like the Green Dragon.

Bottom Line: An engaging, spooky tour ideal for history lovers who want to hear ghost stories over drinks.

12. Sushi Making Class at a Local Brewery in Boston

If you’re craving a hands-on experience, this sushi-making class offers a fun way to combine culinary skills with local brews. Led by an expert chef, you’ll learn to craft gluten-free, nut-free, and dairy-free sushi, starting with a bowl of miso soup.

Although it’s the only experience on this list focused on food preparation, it’s a great option for food and drink lovers who want a break from drinking to learn a new skill. The class lasts about 2 hours and provides a relaxed atmosphere with plenty of expert guidance.

Bottom Line: Perfect for curious foodies who want to learn sushi-making while enjoying a local brewery’s relaxed vibe.

13. Boston: Freedom Trail History Tour and Brewery Taste

This combined history and brewery tour offers a unique way to experience Boston. Led by an expert guide, you’ll explore Freedom Trail landmarks then relax with beer tastings and lunch at Democracy Brewing.

It’s a great choice for those who want a full day of history, local breweries, and good food. The tour covers 11 of 16 historic sites, providing a thorough introduction to Boston’s revolutionary roots and craft scene.

Bottom Line: Ideal for history lovers who want to pair sightseeing with quality beer and a casual lunch.

14. Boston: Pizza, Beer, and Paul Revere Tour

This pizza and beer tour focuses on Boston’s North End, where you’ll walk Paul Revere’s steps while enjoying two slices of pizza and a local pint. The small-group atmosphere encourages a relaxed, friendly vibe, with visits to tucked-away bars and historic landmarks.

Rated highly, guests appreciate the local insights and the chance to see the city through a casual lens. It’s perfect for travelers who want to combine food, drink, and history in a laid-back setting.

Bottom Line: A fun, social way to experience Boston’s North End with good food and local stories.

15. Boston Bar Crawl Back Bay Beat Bar Crawl

Finally, if you’re after a simple, lively bar crawl, the Back Bay Beat Bar Crawl offers an easy way to check out local bars in Boston’s Back Bay. Priced at just $14.99, it lasts about 1.5 hours, focusing on fun and socializing.

While reviews are currently unavailable, this tour is suited for those looking to hop around a few bars with minimal fuss. It’s a good budget option for a quick night out.

Bottom Line: A straightforward, affordable way to experience Boston’s nightlife with friends.

How to Choose the Best Drinking Tour in Boston

When selecting a tour, consider your interests: do you prefer learning history with your beer (pub crawl) or exploring Boston’s craft breweries (brewery tour)? If you love spooky stories, the haunted pub crawl might be perfect. Budget-conscious travelers might opt for the 2-hour pub crawl, while those seeking a comprehensive experience should look at the full-day pub and ferry tour.

Timing also matters—weekends fill up quickly, especially during peak season, so book early if possible. For a more relaxed experience, weekday tours tend to be less crowded. If you’re interested in combining activities, the Freedom Trail and brewery taste offers a full day of sightseeing plus drinks.

Final Thoughts

Boston’s drinking tours offer a wide spectrum—from historic pubs and ghostly tales to craft brewery explorations and culinary classes. For history lovers, the pub crawl along the Freedom Trail provides a lively, educational experience. Beer enthusiasts may prefer the guided brewery tour, with its behind-the-scenes access.

For a spooky twist, the haunted pub crawl and ghostly pub tours add a fun scare factor. Whichever you choose, Boston’s authentic tavern scene and craft breweries will leave you with great stories—and even better drinks. Be sure to book early to secure your spot and enjoy the full flavor of this historic city.