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Wine Tour in Boston
  • Wine Tour in Boston
  • Boston Wine Tour
  • Wine Tasting Experience in Boston
  • Guide for Wine Tour in Boston

Boston Wine Tour

From: $70
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Back Bay, North End & South End - Boston, MA


Back Bay
Saturdays - 3:00 PM
North End
Saturdays- 3:00 PM
South End
Saturdays - 3:00 PM

  • Sip 'n' stroll your way through the vibrant neighborhoods of one of America's most beloved cities, enjoying VIP treatment on the Boston Wine Tour.
    • With locations to choose from, you'll experience the fine wine and celebrated Boston attractions of either the North End, South End or Back Bay.
    • The 90-minute tour will include samples at 2 locations as you wind your way through a Boston neighborhood, rich in history and local culture.
    • Each urban stop invites you to savor a VIP session, featuring lessons on tasting, pairing and buying wine.
    • Meet your guide, a friendly and charismatic wine expert, along with your intimate group of no more than 12 fellow wine enthusiasts
    • Toast to a fun afternoon with family or friends, as you delight in this unique Boston city tour!
    Full Description>
  • A tour of America's famed 'Walking City' just wouldn't be complete without a little strolling and a lot of sipping! Get the best of both options on the Boston Wine Tour!

    Get a firsthand taste of one of the areas as you explore 2 of its best bars and restaurants on this wine-centric walking tour. Meet your guide, a friendly and charismatic wine expert, along with your intimate group of no more than 12 fellow wine enthusiasts.

    At each stop, you will delight in a VIP wine tasting experience. Reserved seating will be ready and waiting for your group's arrival, along with a top-notch serving staff. Pre-selected wines will be prepped for pouring, alongside appetizers (where appropriate) to demonstrate intriguing pairings. Your hosts will also present fascinating wine lessons as you sip and savor, enlightening you with knowledge regarding how to taste, pair and even buy wine.

    With 3 different neighborhood touring options to choose from, you'll soon discover why each area is a Boston favorite!

    Marvel at the artistic influence of the South End, admiring its sophisticated and diverse surroundings as you make your way between tasting stops. Or opt to enjoy your Boston Wine Tour in a more vintage fashion, taking in the atmosphere of the city's oldest neighborhood, the North End. And if you prefer to immerse yourself in the lap of luxury, head to Back Bay for a Boston tour that takes you ambling among one of the most affluent areas of the city.

    Depending on which route you select, your 2 tasting locations may include the following venues (subject to change):

    • Aragosta Bar & Bistro
    • Scopa
    • Post 390
    • L'Espalier
    • Stephi's on Tremont
    • Masa
    • Rigoletto
    • Artu
    • Gaslight du Coin
    • Cinquecento
    • Legal Seafoods
    And best of all, no matter which Boston Wine Tour option you explore, you're in for a relaxed outing that will prove to be a splendid combo of fun, entertainment and education. So enjoy the charm and humor of your wine ambassador, and raise a glass to enjoying one of the most unique things to do in Boston, in the company of fine wine!
    Key Info>
  • Essential Information

    • Participants must be at least 21 years of age
    • Gratuity is not included, but is appreciated if you enjoy the tour
    • Participants will be required to walk approximately one mile on a relatively flat route


    90 Minutes

    Maximum Participants

    Up to 12 participants per tour


    This experience is only for those on the tour.

    Weather Dependent

    This experience is not weather dependent and is held rain or shine regardless of weather conditions. Please bring an umbrella during the winter months, just in case. Always contact your experience provider with any questions about weather conditions.

    What To Wear

    Wear comfortable clothing appropriate for walking and weather conditions.

    Booking Information

    For this experience, it is recommended to request bookings at least 14 days in advance.

    Cancellation Policy

    Prior to scheduling/booking a date for this experience, Cloud 9 Living's standard return and exchange policy shall apply. Once you have scheduled a date and have received a booking confirmation, all bookings are final and no cancellations will be allowed.

    Experience ID


    1. Are there any tour requirements?
      Please have a valid driving license or passport to present to our Wine Ambassadors when you arrive. You will not be served any alcohol without proper identification verifying you are 21 years of age or older. This applies to all guests.
    2. Should I eat before I come on the tour?
      Yes! These wine tours feature delicious and delectable wines. The wine destinations are focused on wine tasting not food pairings. It is strongly recommended you come on a full stomach.
    3. How much wine will be sampled on the tour?
      Over the course of 90 minutes the tour will taste 4 - 6 different varietals. You will sample the equivalent of 2 - 2.5 glasses of wine.
    4. How much walking is involved on the tour?
      The tours are focused on premier wine destinations in select neighborhoods. You will walk no more than 0.6 miles during the 90-minute tour. Walking shoes are suggested but not required.
    5. Can I bring children on the tour?
      We love kids, however, the wine tour is not a suitable environment for children. The tour will include drinking, learning and exploring Boston in a mature format.
    6. Do we just drink and walk around?
      No way! You will explore select Boston neighborhoods through wine and history. You will hear stories that pair wine and culture via your renowned Wine Ambassadors.
    7. Is the tour wheelchair accessible?
      Yes, the tour can accommodate wheelchairs.
    8. Are Wine Ambassador gratuities included in the price of the tour?
      Gratuity for your tour guide is not included but is appreciated if you enjoy the tour. Recommended gratuity is $8 -$12 per person.
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