15 Best Boston Beer, Wine and Food Tours

From Paul Revere and Samuel Adams to the Boston Tea Party, Boston Massachusetts is arguably the most historic city in all of America.

With only slightly more than 600,000 residents, it’s not large by modern city standards, but it’s got a well-earned reputation as a tough town that fiercely protects its heritage and traditions – and one that loves its beer and baseball too.

Due to its proximity to some of New England’s most historic and natural wonders, it’s a great stepping-point for other quick trips to the surrounding area.

Below are 15 of the best beer, wine and food tours in Boston.

1. The Original Boston Brews Tour

VIP Brewery & Beer-Tasting Tour with Lunch

Boston has always had a reputation as a town that enjoys its beer; if you’ve got a few hours to kill, there’s no better way to taste more of Boston’s favorite brews than by guided tour.

The tour includes stops at a few of the area’s most friendly taverns and breweries, where in addition to a thorough sampling and having nearly 100 different draft beers at your fingertips, you’ll also enjoy a great lunch.

From dark beer to light and almost everything in between, this tour has it all. It’s a great way to learn about the city’s history and meet some likeminded locals too.

2. Fenway Park History Pub Crawl

Fenway Park Baseball History Pub Crawl

Few things go together as well as baseball and beer, and when in a city like Boston that loves both, enjoying them together is a must.

This tour’s guide will be a local foodie, beer fanatic, and lover of all things baseball, so it’s really like getting three for the price of one.

You and your travel partners will hit at least three bars that are fan favorites, and a local brewery just a stone’s throw from the stadium.

If you’re lucky enough to go during baseball season, the atmosphere will be intense, but fear not, even if it’s the offseason the bars draw a great crowd.

3. Historic Taverns and Pizza Tour

Historic Taverns And Pizza Tour

Walking tours are a great way to get some exercise, see the sights up close, and get a great feel for the layout of a city.

This 2 ½-hour tour focuses on taverns and pizza – two things that go together like peanut butter and jelly.

On the tour, you’ll visit some of the region’s most historic landmarks, many of which date back to the country’s colonial days.

In bygone eras, taverns were often rallying points for tipsy patriots itching for a fight with the colonial rulers of whom they weren’t too fond. This tour will take you to some places that were once the haunts of some well-known historical figures.

4. Guided Brewery Tour with Drinks and either Lunch or Dinner

Guided Brewery Tour

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Guided Brewery Tour

Microbreweries and brewpubs are all the rage in Boston. Along with some of the city’s larger and more well-known breweries, they give Boston a beer culture that’s very unique.

On this tour, you’ll sample nearly 20 beers and learn about the brewing process.

If you’re staying downtown, door-to-door transportation is included. Depending on the tour you choose, it will either include lunch or dinner.

Even though a meal is included, it’s best not to show up on an empty stomach as some of the beers you’ll try are pretty strong. You wouldn’t want to fall asleep before you’ve gotten your money’s worth!

5. Historic Pub Crawl Tour along the Freedom Trail

Historic Pub Crawl Tour Along The Freedom Trail

Boston is one of the country’s most historic cities, and with such a rich beer history, this pub crawl along Freedom Trail is a great way to get your fill of both.

The crawl will lead you to many historic downtown pubs that are food and drink favorites of the locals -many of which are some of the oldest pubs in the country.

The tour lasts about 2 ½ hours. Like many guests, you may find yourself striking out on your own after the tour and revisiting some of the places you’ve just seen, making a night of it.

6. Food and History Tour from the North End to the Freedom Trail

North End To The Freedom Trail – Food & History Tour

In case you weren’t paying attention in elementary school history, Boston Harbor is one of the most historic areas in the country and is considered the birthplace of the Revolution.

This walking tour includes stops at historically important areas along the harbor and wharf, which runs along Atlantic Avenue.

You’ll stop into a few shops and eateries, and take an afternoon break for an espresso and a pastry.

Faneuil Hall, Quincy Market, and the Old State House are on the itinerary as well. Near the end, you’ll wind through picturesque Beacon Hill, one of the city’s gems.

7. South End Wine and Walking Tour

South End Wine And Walking Tour

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South End Wine And Walking Tour

Though pretty much everybody knows about Boston’s ages-old beer tradition, what’s not so well known is that the city has undergone a bit of a wine renaissance lately too.

This tour of the city’s South End winds its way through Victorian-era flats, quaint shops, and plenty of restaurants, cafes, and bars that are usually full of cheerful revelers.

At each wine tasting stop, you’ll enjoy reserved tables, food selected specifically to go with your wines, and knowledgeable staff that’ll walk you through the samples and give you a refreshing insight into the finer points of wine-snobbery.

8. Independence Pub Crawl

Independence Pub Crawl

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Independence Pub Crawl

With so many pubs and pub crawls in the city, it’s a wonder you can even walk down the sidewalk without stumbling over inebriated tourists.

For those who’ve only got a few hours to spare, this short but fun pub crawl gives guests the option of choosing what time of the day best suits them.

The tour is led by a local history and spirits aficionado, who’ll take you to some popular and historically significant pubs, where you’ll be able to sample many of the city’s microbrews and hard ciders too.

Food and tips aren’t included, so bring a few extra bucks.

9. Back Bay Walking and Wine Tasting Tour

Back Bay, Boston

Source: Marcio Jose Bastos Silva / shutterstock

Back Bay, Boston

Boston’s Back Bay is a trendy area and one especially popular with those who like experiencing the city’s history while sampling some amazing cuisine and wines that were just made for one another.

If you’re not up on wine terms and pairings, fear not, your guide will tell you all there is to know so you can get the most bang for your buck.

Hotel pickup and drop-off aren’t included, but if you’re staying downtown you may be able to walk to the meeting point.

Since it’s a walking tour, be sure to wear a pair of comfy shoes.

10. Sip of Boston Brewery Tour

Sip Of Boston Brewery Tour

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Sip Of Boston Brewery Tour

Of all the famous brands of beer brewed in Boston, Samuel Adams is probably the most well-known. Though it started out small, it has grown significantly and now ships its flagship Boston Lager all over the country.

On this tour, you’ll visit the brewing facilities of Samuel Adams and Harpoon and get a fascinating historical insight from the tour’s knowledgeable and enthusiastic guide.

From pilsners and stouts to wheat beers and pale ales, you’ll sample many of the most popular, and probably a few that you’ve never even heard of.

Bottled water and snacks are included, as is bus transportation.

11. North End Wine and Walking Tour

North End Wine And Walking Tour

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North End Wine And Walking Tour

When visiting a new city, it can be difficult to get a feel of where things are before it’s time to pack your bags and head home.

If that sounds like you, consider a walking tour, which will not only get you some exercise and an up-close-and-personal view of the city but on this tour will include some of the region’s best wines.

Group size is limited to 12; you’ll explore Boston’s Little Italy and your wines will be paired with some delectable sweet and savory treats that’ll really satisfy that sweet tooth of yours.

12. Cocktails and Cannoli

Cocktails And Cannoli

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Cocktails And Cannoli

If paired correctly, cocktails and sweets can go together nicely, and though Boston is predominately Irish, it’s also got a thriving Italian community that’s especially known for its cannoli.

This tour includes stops to some of the area’s most noted bakeries. You’ll even watch chocolate being made, after which you’ll get to satisfy those taste buds by sampling tiramisu and cannoli along with your cocktail.

The tour lasts about 2 ½ hours. During that time you’ll learn a great deal about the area’s fascinating history too.

Though this tour is brief, it’s a great value for your time and money.

13. South End Food and Drink Tour

South End Food And Drink Tour

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South End Food And Drink Tour

Boston’s South End is one of the city’s most famous neighborhoods and has been notably featured in many popular movies about the gangsters who made their names there.

Though the area was once an Irish stronghold, it’s become more diverse lately. On this tour, you’ll stop into a few shops that may seem out of place with their remarkably international cuisine.

The architecture is amazing too, as is the area’s rich history and the amazing restaurants serving lots of traditional classics and some with a contemporary twist.

The tour includes a fair amount of walking and lasts about 3 ½ hours.

14. New England’s Beaches, Beers and Bluffs

New England’s Beaches, Beers And Bluffs

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New England’s Beaches, Beers And Bluffs

If you’ve got a wide-open itinerary, a pocket full of credit cards, and want to experience all that New England has to offer in one tour, then this is for you.

This seven-day tour includes visits to neighboring states like New Hampshire, Maine, and Vermont. Along the way, you’ll see some amazing natural beauty, learn about the area’s colonial history, and sample some of the region’s most famous and delicious beers too.

Highlights include a Maine lobster cruise and a visit to the Trapp Family Lodge in Stowe.

There’s just too much to list, so check it out thoroughly before booking.

15. North End Secret Food Tour

North End Secret Food Tour

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North End Secret Food Tour

Boston is one of those cities that’s full of unique and distinct neighborhoods that have their own food, feel and history.

This three-hour walking tour is limited to 12 people and will lead you through the city’s North End. Your guide will take you to some of the neighborhood’s most diverse and delectable restaurants, where you’ll sample seafood, sweets, beer, and wine, all while rubbing elbows with some locals and getting to know your travel mates.

Things will get kicked off with a lobster roll, and you’ll try pizza, homemade sausages and some craft beer too.

Where to stay: Best Hotels in Boston, Massachusetts (MA)
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15 Best Boston Beer, Wine and Food Tours:

Back Bay, Boston