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Experience the best of Boston’s burgeoning wine scene on this 2-hour wine-tasting tour at some of the city’s finest restaurants. Choose from one of four tours, each highlighting a different neighborhood in the city: Harvard Square, South End, North End or Back Bay. Learn about each area while sipping six varieties of wine at three restaurants. An expert guide will advise on what wine to select and what foods to pair each with. Tour is limited to 12 people to ensure an intimate experience.


  • 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 the guide to begin one of these walking wine tours of downtown Boston. Venture past historic sites en route to one of four neighborhoods, each with its own unique offerings. Your guide, who has advanced certification in viticulture, will entertain you with wine history and wine selection tips and a discussion of Boston’s culinary scene.

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 American, Mediterranean and Italian cuisine. You’ll enjoy a world-class selection of wines, with an emphasis on sparkling wines, hailing from Spain, France and the US.
  • Nubar Restaurant and Lounge: a chic restaurant inside the Sheraton Commander Hotel with an eclectic wine list featuring French classics as well as South American and California vintages. Sip Spanish cava and California sparkling wine, nibble on fruit and local cheeses, and learn how French Champagne is made.
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.
  • Gennaro’s, 5 North Square – the oldest square in America, a quiet retreat located steps from busy Hanover Street. With it’s cobblestone streets and gas lamposts, North Square is one of the most romantic spots in the North End and Boston. The cuisine at Gennaro’s is traditional Italian home cooking with fresh seafood specialties served daily.
  • Tresca: sample delicious Italian varietals paired with wonderful Northern Italian specialties. Discuss different Italian wine regions.
  • 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 July 2016

Enjoy every minute of this experience, Roz was truly knowledgeable in her wines. she was very sweet and got the job done. Learned a lot of new things about wines both red and white. I do think it was a bit pricey for only 2 restaurants and wine store.....think there should be more like 4, even three with the end being desert wines with desert to help close up the tour.......

Kathleen M

5 star rating: Highly Recommended May 2016

Very informative on the wines we tried and the restaurants were a good choice!

Paul S

5 star rating: Highly Recommended April 2016

The North End wine tour was great. Our tour guide was extremely friendly and knowledgeable on various types of wines. i would highly recommend this tour to anyone trying to plan a nice afternoon in the north end.

Robert L S

5 star rating: Highly Recommended February 2016

Raz was great! Learned a lot and tried some great wines! Given this was Italian wine based, there were more red wines than white - only suggestion would be to even it out a bit more.

Other than that, it was a great day! Gave it to my mother as a gift for Christmas and she loved it. Good snacks and a good time.

laurence d

5 star rating: Highly Recommended November 2015

Lin was very knowledgeable. Really learned alot from her.

Court P

5 star rating: Highly Recommended July 2015

Lot's of fun!

Jeffrey V

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.

Tracy Q

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!

Mary M

5 star rating: Highly Recommended December 2014

This wine tour was amazing! It was run by an extremely smart sommelier. I feel like I know so much about wine after this trip!!!

Mitch-Stuart Inc

5 star rating: Highly Recommended September 2014

Amazing. We had a wonderful time. Phenomenal Wine Tasting

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