5 star rating: Highly Recommended 4 Reviews

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  • Location: Boston, Massachusetts
  • Duration:  2 hours (approx.)
Experience Boston’s dynamic wine culture as you sip wine and sample food at several award-winning restaurants! This walking tour takes you at a leisurely pace through one of Boston’s historical neighborhoods – Harvard Square, South End, North End or Back Bay – where you’ll gain insight about each location between tastings. Learn about wine from an expert guide, who will share tips about wine selection, food pairings and Boston’s acclaimed culinary scene. Numbers are limited to 12 people, ensuring an intimate experience with a small group of like-minded wine lovers.


  • Two-hour Boston wine tasting and walking tour
  • Stroll through one of Boston’s historical neighborhoods
  • Taste up to six different varietals at three upscale venues
  • Learn about wine history as you pair delectable food and wine
  • Choose from four tours: Harvard Square, South End, North End or Back Bay
  • Small-group tour limited to 12 people ensures a personalized experience with a knowledgeable guide

What You Can Expect

Boston Wine Tasting and Walking Tour

Wine Tasting

Meet your guide and small group in one of four unique neighborhoods, and embark on a walking tour past historical sites, stopping at upscale establishments for private wine and food tastings along the way. With advanced certification in viticulture, your guide will entertain you with information about wine history and wine selection amid Boston’s thriving culinary scene. Taste six varietals – about two to four glasses – of hand-selected wine at award-winning restaurants, luxury hotels and gourmet wine shops. You’ll find that learning about wine is as much fun as drinking it!

Choose from four different wine tours that explore Boston’s historical neighborhoods: Harvard Square, South End, North End and Back Bay. (See descriptions of each tour and a list of venues under Itinerary below.)


Option 1: Harvard Square
Get a glimpse of Harvard Square’s vibrant restaurant culture and learn interesting yet little-known facts about America’s oldest university while sampling award-winning Mediterranean, New England and Italian cuisine. You’ll enjoy a world-class selection of wines from Spain, Italy and France!

  • The Sheraton Commander Nubar: a chic restaurant with an eclectic wine list featuring French classics as well as exciting South American and California vintages.
  • PARK: a menu of New American classics from Chef Mark Goldberg and an inspired selection of international wines in a rustic-meets-luxury subterranean space.
  • First Printer: an exclusive tasting in the ‘Vault’ includes New World wines paired with delicious small bites of traditional American cuisine with New England flare.

Option 2: South End
Explore the gastronomical diversity of Boston’s ‘Restaurant Row’ with a unique and eclectic sampling of Southwestern, Modern American and French cuisine. Enjoy a handpicked selection of wine from Burgundy and Rhone in France, Patagonia in Argentina, and Puglia in Italy – combined with an old-world rustic French culinary style and new-world American innovation.

  • Gaslight Brasserie: a classic neighborhood Parisian brasserie with warm and inviting décor, including a hand-crafted Parisian zinc bar, reclaimed wood floors, mosaic tiles and beamed wood ceilings.
  • Cinquecento: a 250-seat restaurant featuring provincial Roman cuisine from Chef Chris Robins, a 100-bottle wine list and an Italian onyx marble bar.
  • Masa: an award-winning menu, pairing flavors and cooking styles of southwestern cuisine with local New England ingredients.

Option 3: North End
Learn about grapes, Italian food pairings and entertaining history while sampling Pinot Grigio, Sangiovese, Prosecco and Pinot Bianco. Taste the wines of Tuscany, Piedmont, Abruzzo and more through a top-tier collection of North End establishments.

  • Aragosta at Fairmont Battery Wharf: a sophisticated urban waterfront retreat surrounded by shopping, fine dining, stunning coastal views and the rich historical setting of downtown Boston.
  • Davide Restaurant: a Wine Spectator Award-winner for 15 years and counting!
  • The Wine Bottega: a cozy gem with wine tastings in an authentic and sophisticated wine cellar.

Option 4: Back Bay
Admire the beautiful architecture of 19th-century American-Victorian urban design and sample the best Italian, classical New England and French cuisine along with exquisite French Cabernets, Sicilian Marsalas and many other selections.

  • Legal Seafoods: a 40 page-wine list and an award-winning wine cellar, which holds more than 10,000 bottles and 800 different labels in a comfortable lounge three fathoms below ground.
  • Maggiano's Boston: authentic Italian food and Italian wine in the comfort of a VIP room.
  • L'Espalier Restaurant: the first independently owned restaurant to bring haute cuisine to Boston.

Customer Reviews

5 star rating: Highly Recommended February 2015

My whole family thoroughly enjoyed this event! Our tour guide Lynn was fantastic and the other members of our event were great party guests. We would highly recommend this very enjoyable (and eductational) event for anyone looking for a different type of fun.

5 star rating: Highly Recommended February 2015

Roz was extremely knowledgeable in all aspects of wine. I learned more than I expected and tasted some of the best wines. We even bought a case of wine from the Wine Bottega on Hanover. I would highly recommend this tour if you are looking to gain some experience in wine and want to take a course in a short amour of time. Well worth it!

From USD $ 66.00

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Tour code: 5949CWT


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