Which Boston Drinking Tours To Choose? Our Best 14 Picks

Boston’s unique blend of history, vibrant neighborhoods, and craft beer scene makes it a perfect city for drinking tours. Whether you’re interested in historic pubs along the Freedom Trail or eager to explore Boston’s thriving craft brewing scene, this city offers plenty of options that combine storytelling with a good pour. We particularly love the Boston Freedom Trail History Pub Crawl because it seamlessly blends iconic landmarks with local taverns, giving you a taste of both history and hops. Another favorite is the Signature Boston Guided Brewery Tour with snack, which offers a behind-the-scenes look at Boston’s small breweries and cider houses—perfect for beer aficionados. Each of these tours provides an authentic experience that’s both fun and educational, making Boston a top destination for drinking enthusiasts.

Quick Overview

Our list includes a mix of pub crawls, brewery tours, haunted pub experiences, and even a sushi-making class at a local brewery. For a comprehensive look at Boston’s historic pubs and taverns, check out the Boston Historic Pubs with Food & Drink, Ferry & Walking Tour. If craft beer is more your style, the Signature Boston Guided Brewery Tour with snack offers a relaxed taste of Boston’s beer scene. For those who love spooky stories, the Boston Haunted Pub Crawl combines ghost tales with great drinks. Each experience is designed to suit different interests—whether that’s history, craft brewing, or a spooky night out.

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

At number 1, this small-group pub crawl combines Boston’s historic landmarks with friendly taverns. Starting outside the Samuel Adams statue at Faneuil Hall, your guide takes you along the Freedom Trail, stopping at some of the city’s top historic pubs. The tour offers two options: the Happy Hour tour, which includes four draught beers or ciders, or a Dry Run where you can purchase drinks freely. Guests love the informative guides like Julia, who make history alive while you sip local brews. The tour’s focus on America’s early years and its mix of history and humor makes it engaging—perfect for those who want a casual, fun evening with a historical twist. The small-group setting ensures personalized attention, often leading to friendly conversations and new friends.

Bottom Line: This tour is ideal for history lovers who want to pair storytelling with a lively pub atmosphere. It’s a good value at $60 per person for around 2 hours 15 minutes, especially with the option to enjoy four beers. If you’re short on time but want a fun, educational experience, this one checks all the boxes.

2. Signature Boston Guided Brewery Tour with snack

Number 2 on our list is the Signature Boston Guided Brewery Tour, which dives into Boston’s craft beer scene with detailed visits to local breweries and cider houses. For around $119, you get around three hours of behind-the-scenes access, tasting up to 12 different beers and ciders. The tour visits well-known spots like Samuel Adams and the Lamplighter, along with newer microbreweries, providing a well-rounded view of Boston’s brewing diversity. The transportation in an air-conditioned van makes it comfortable, especially in summer. Guests praise the knowledgeable guides like Bill, who share stories about the breweries’ histories and brewing processes. The included snack helps soak up the alcohol and adds a nice touch.

Bottom Line: If you want an immersive experience with VIP access, multiple tastings, and transportation, this tour offers excellent value. It’s best suited for beer enthusiasts who want an in-depth look at Boston’s craft brewing and cider-making.

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

This history-meets-happy hour tour combines Boston’s famous Freedom Trail with visits to hidden bars and historic taverns. Led by a local beer expert guide, the tour offers tastings of local Boston brews while sharing stories about the city’s revolutionary past. Guests learn how beer played a role in events like the Boston Massacre, all while exploring neighborhoods rich in colonial architecture. The tour lasts about 2 hours and can be customized with different options, making it flexible for various interests. Reviewers highlight the fun mix of history and beer, with guides providing insider tips on local brewing spots.

Bottom Line: Ideal for history fans who want to enjoy authentic local beers in historic settings. It’s a reasonably priced way to combine education and entertainment.

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

For about 3.5 hours, this small-group tour takes you through some of Boston’s most historic neighborhoods like Beacon Hill, North End, and Charlestown. Starting in the North End—aka Little Italy—you’ll sample local tavern snacks and enjoy scenic ferry rides across Boston Harbor. Inside historic pubs like Warren Tavern, you’ll learn unique stories about American Revolution heroes and sip drinks where Washington, Adams, and Revere once gathered. The tour is praised for its personalized experience and the combination of walking, ferry, and pub visits. The inclusion of a ferry ride adds a scenic touch, and the food and drinks provide a true taste of Boston’s tavern culture.

Bottom Line: This tour suits those who want a combination of history, food, and scenic views, making it perfect for a memorable afternoon with a small group.

5. 2 Hour Historic Pub Crawl in Boston

At number 5, this 2-hour guided pub crawl hits two of Boston’s iconic taverns: the Green Dragon and The Bell in Hand. Led by a local guide, you’ll learn about Boston’s brewing history while sampling classic beers. The tour’s short duration makes it a great introductory experience for visitors with limited time. Guests consistently praise the knowledgeable guides and the authentic historic atmosphere of the pubs, which have been serving locals for centuries. It’s a budget-friendly option at just $35, making it accessible for most travelers.

Bottom Line: Best for those wanting a quick, fun taste of Boston’s historic pubs without a big time commitment. Ideal for an evening or a layover day.

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

Number 6 offers a spirited twist—a haunted pub crawl exploring Boston’s spookiest taverns. For 2 hours, your guide shares ghost stories tied to locations like Ned Devine’s and the Green Dragon Tavern, where Revolutionary War figures once drank. It’s a perfect choice for those who love a little supernatural suspense with their drinks. The tour lasts about 2 hours and is praised for informative storytelling and a fun, eerie atmosphere. Prices start at $35, making it affordable for a unique night out.

Bottom Line: This is a great pick for history and ghost enthusiasts who appreciate a dash of spooky folklore with their libations.

7. Boston: Guided Craft Brewery Tour with a Snack

Close to the top, this 3.5-hour guided craft beer tour features VIP access to three local breweries, allowing you to see the inner workings and brewing processes firsthand. Participants taste up to 12 samples and enjoy a tasty snack to complement their drinks. Guides like Joe are praised for their extensive knowledge about the brewing process and local beer history. The tour’s focus on small breweries and regional collaborations makes it perfect for those wanting to understand Boston’s craft scene beyond just tasting.

Bottom Line: For serious beer lovers craving an educational experience, this tour offers value and insight that’s hard to beat.

8. Pizza Beer and Paul Revere Tour

Number 8 combines Boston’s best pizza, local beer, and Revolutionary history. Starting in the North End, your guide Jimbo takes you on a relaxed walk through historic streets, stopping at brick oven pizzerias and hidden bars. The focus is on authentic local eats and drinks, with plenty of stories about Paul Revere and the city’s colonial past. Guests love Jimbo’s casual, friendly style and the chance to experience off-the-beaten-path spots. The tour lasts about 2 hours and is perfect for those who want a laid-back evening with good food and history.

Bottom Line: Ideal for foodies and history fans who want a fun, informal way to see Boston’s North End.

9. Boston Haunted Pub Crawl

This haunted pub crawl takes you through Boston’s most haunted bars and historic pubs**, including the 21st Amendment and Emmet’s Pub. With a focus on ghost stories and haunted locations, it’s perfect for those who like a little spooky atmosphere with their drinks. The tour lasts about 2 hours and features interesting tales about Boston’s ghostly past. Rated at $29.99, it’s a budget-friendly option that combines history, horror, and good drinks.

Bottom Line: Best suited for history and ghost story fans looking for a fun, spooky night out.

10. Boston Ghosts Boos and Brews Haunted Pub Crawl

Number 10 offers a small-group experience exploring Boston’s haunted pubs. It features stories about restless spirits at historic locations like the Union Oyster House and Green Dragon Tavern. The tour lasts two hours and emphasizes personalized storytelling. Priced at $36, it’s a good option for those interested in ghost lore with a casual drink in hand. Reviewers mention its entertaining guides and authentic atmosphere.

Bottom Line: Perfect for ghost story lovers who want a relaxed, fun exploration of Boston’s haunted history.

11. Sushi Making Class at a Local Brewery in Boston

This unique experience combines culinary skills with Boston’s brewery culture. Over 2 hours, you’ll learn to make gluten-free, nut-free, and dairy-free sushi with an expert chef. The class includes a bowl of miso soup and hands-on instruction, all enjoyed at a local brewery. Guests with a sense of adventure and interest in food craft will love this intimate class. It’s rated highly for its personalized instruction and relaxed atmosphere. It’s a good change of pace for those who want more than just drinks.

Bottom Line: Suited for food lovers wanting a fun, hands-on activity that combines cuisine and local brewing.

12. Boston: Freedom Trail History Tour and Brewery Taste

Number 12 offers a combination of historical walking tour and beer tasting. Led by an expert historian, you’ll visit 11 of the 16 Freedom Trail landmarks, then enjoy beer tastings and lunch at Democracy Brewing. For history and beer enthusiasts, this tour balances education and refreshment seamlessly. The all-inclusive approach makes it a great value, especially for those wanting an immersive experience. The tour’s reviews highlight the engaging guides and the quality of the local brews.

Bottom Line: A solid pick for history buffs who want to finish with a relaxed beer tasting and lunch.

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

This tour is all about enjoying authentic North End pizza and local beer while walking in Paul Revere’s footsteps. Led by a friendly guide, it emphasizes small-group intimacy and hidden local spots. It’s a casual, fun way to experience Boston’s culinary and revolutionary history in one go. Guests love the laid-back vibe and the insights into local traditions. The tour lasts about 2 hours, making it a perfect short but rich experience.

Bottom Line: Best suited for foodies and history lovers who prefer a relaxed, informal tour packed with flavor.

14. Boston Bar Crawl Back Bay Beat Bar Crawl

The newest addition, this Back Bay bar crawl offers a quick, lively experience lasting about 1.5 hours. While reviews are limited, the focus is on hopping between popular bars with a DJ, making it perfect for those wanting a party atmosphere. It’s affordable at $14.99 and designed for a fast-paced night out. Ideal for locals or visitors looking to enjoy the nightlife with minimal fuss.

Bottom Line: Great for short, energetic nights in Boston’s nightlife district, especially if you enjoy music and mingling.

How to Choose Your Drinking Tour

When deciding between these options, consider your budget, time, and interests. For history buffs who want a relaxed experience, the Boston Freedom Trail History Pub Crawl offers a perfect blend of storytelling and local pubs. If craft beer is your passion, the Signature Boston Guided Brewery Tour provides in-depth tastings and behind-the-scenes access. For those intrigued by spirits and spooky tales, the Haunted Pub Crawl and Ghosts Boos and Brews are fun options. Budget-conscious travelers might prefer the 2-Hour Historic Pub Crawl or the Boston Bar Crawl Back Bay Beat. Always check schedules and book early, especially during peak summer months.

Boston offers a fantastic range of drinking tours that cater to history lovers, craft beer enthusiasts, haunted story fans, and casual pub crawlers. Whether you want to walk in Paul Revere’s footsteps, sip craft brews behind the scenes, or explore Boston’s haunted taverns, there’s something for all. We recommend pairing a historic pub crawl with a scenic ferry ride or trying a guided brewery tour for a more in-depth experience. No matter your choice, booking early ensures you won’t miss out on these memorable adventures. Cheers to discovering Boston, one pint at a time!