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Top Massachusetts Wine Tasting & Winery Tours

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6 Tours and Activities

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Free Cancellation:Get a full refund up to 24 hours in advance on most experiences.See Details

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Boston Back Bay Wine Tasting Tour

Experience the best of Boston’s burgeoning wine scene on this 2-hour wine-tasting tour at some of the Bay Bay's finest restaurants. Learn about the historic area while sipping delicious wine varietals and enjoying tasteful food pairings. An expert guide will advise on what wine to select and what foods to pair each with. Tour numbers are limited to ensure an intimate experience.
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  • 2 hours
From  
US$75.00
From  
US$75.00
Learn More
  • 2 hours

NEW TO VIATOR

The Original Paint Nite Boston by Yaymaker

If you're looking for a night out in Boston, with a twist, don't settle for a regular old night at the bars. Instead unleash your inner artist at the Original Paint Nite by Yaymaker. Perfect for beginners and aspiring artists alike, you can grab a drink—at your own expense—and follow along with your host to start creating. By the end of the night, expect to turn a blank canvas into a work of art that you're free to take home.
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  • 2 hours
  • Free Cancellation
From  
US$27.00
From  
US$27.00
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  • 2 hours
  • Free Cancellation

Boston North End Wine Tasting Tour

If you’re not from the Boston area, it can be difficult to know where to go to taste some of the city’s best wine. This North End wine tour is led by a guide who takes you to the historic neighborhood’s elite local restaurants and well-curated wine shops for Italian wine pairings. Learn about the vintages and varietals of Italy in Boston’s Little Italy with a small-group limited to 12 for personalized attention the whole way.
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  • 2 hours
From  
US$75.00
From  
US$75.00
Learn More
  • 2 hours

Wine and Wine Jelly-Sauce Tasting on Plymouth Bay

Experience true local wines with a tasting at Plymouth Bay Winery, where talented vintners and chefs create wines, wine jellies and wine sauces from fruits that are native to the northeastern United States. Sample the entire collection of wines, and learn about using the jellies and sauces in your home cooking. Finish the tasting with an etched, commemorative glass from this unique winery in ‘America’s Hometown,’ just a stone’s throw away from historic Plymouth Rock.
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  • Flexible
  • Free Cancellation
From  
US$7.00
From  
US$7.00
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  • Flexible
  • Free Cancellation

Boston South End Wine Tasting Tour

The South End is one of Boston’s most vibrant neighborhoods, filled with Victorian brownstones, bustling restaurants, and a thriving bar scene. On this wine-centric walking tour you can experience some of the area’s best dining and drinking spots, dig into small plates, and learn how to taste, pair, and buy wine. The tour also offers a smooth dining experience, with a reserved table at each location and wait staff standing by to serve pre-selected wines.
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  • 2 hours
From  
US$75.00
From  
US$75.00
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  • 2 hours

NEW TO VIATOR

Boston Wine Tours, Food and Wine

One of the only tours in Boston owned by a real Bostonian. with tons of experience about food, wine. and history. 6 different wines paired with food! Fun, scenic, and very memorable. Come have some wine on the Sea Port!
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  • 2 hours
From  
US$70.00
From  
US$70.00
Learn More
  • 2 hours


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(888) 651-9785