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Boston has no vineyards, so a wine tour in the city means one of three things: a guided tasting at one of its two urban wineries, City Winery Boston near North Station or Boston Winery in Dorchester; a North End food walk with a wine stop; or a do-it-yourself walk between a winery and a wine bar. To walk among real vines, drive out of the city to a farm winery such as Nashoba Valley Winery in Bolton.
BostonVacay does not run tours. Here is what each option involves and how to book it.
Boston wine tour options at a glance
| Option | Where | What you get | Booking |
|---|---|---|---|
| City Winery Boston | 80 Beverly St, near North Station | Guided tasting of five wines made on site | Resy; walk-ins welcome |
| Boston Winery | 26 Ericsson St, Dorchester | Tastings and food-and-wine pairings in a restored factory | Reservations required |
| Off the Eaten Path | North End | Three-hour food walk with a wine shop stop | Online, through the tour site |
| Do-it-yourself walk | Downtown and the North End | City Winery plus a wine bar such as haley.henry | Walk-in or Resy |
| Nashoba Valley Winery | Bolton, outside Boston | Tastings at a working orchard and vineyard | Reserve up to 30 days ahead |
Are there wineries in Boston?
Yes, two, and both make wine in the city from grapes grown elsewhere.
City Winery Boston
City Winery Boston on Beverly Street is a working winery, restaurant and live-music venue in one building. It sources grapes from major American growing regions and makes the wine on site. Its guided tasting, led by one of its wine professionals, pours five wines and explains what makes each one distinctive. Walk-ins are welcome, but reservations through Resy are recommended. It is the closest thing in Boston to a winery tour you can book on short notice, and it pairs easily with a show or a game at TD Garden.
Boston Winery
Boston Winery is a family-run urban winery in a restored 1800s horseshoe-nail factory on the Dorchester waterfront. Its wines are made from fruit sourced in California, Italy and Washington State, and it runs guided tastings, food-and-wine pairings and seasonal socials. The taproom is open Saturdays from 1 to 7 p.m., with pairing events on other dates; space is limited, so reserve through its calendar. It is out of the center, so plan on a car or rideshare.
Is there a walking wine tour in Boston?
We could not confirm a dedicated, wine-only walking tour operating in Boston in 2026. City Wine Tours, which ran weekend wine walks in the North End, South End and Back Bay for years, had no working website when we checked, so contact it directly before planning around it.
The closest current option is Off the Eaten Path, a three-hour North End food walk running since 2012 and led by its founder. It is a progressive lunch through regional Italian food, with a stop at a wine shop for wine education alongside olive oil, balsamic, prosciutto and cheese.
To build your own walk, start with a tasting at City Winery, then walk to Downtown Crossing for haley.henry at 45 Province Street, a natural-wine bar that pours small-production wines by the glass and half bottle with tinned fish, crudo, cheese and charcuterie. It opens from 3 p.m. Tuesday to Friday and noon on Saturday, and is closed Sunday and Monday.
Vineyards near Boston for a day trip
For vines and tasting rooms, go west. Nashoba Valley Winery in Bolton is a 50-acre farm with an orchard, vineyard, distillery, brewery and restaurant. It offers seated tastings at the bar and on the terrace; reservations open 30 days ahead, and after 7 a.m. each day it takes walk-ins. You will need a car or a hired driver.
Before you book
- You must be 21 and carry photo ID for any tasting in Massachusetts.
- Boston Winery's Saturday taproom has limited space, so reserve before you go; City Winery takes walk-ins when it has room.
- Pair a wine stop with history: our Boston tavern tour and North End food tour reviews cover the neighborhoods, and things to do in downtown Boston fills the rest of the day.
Sources: City Winery Boston tastings; Boston Winery; Off the Eaten Path; haley.henry; Nashoba Valley Winery; Google Places status for each business. Checked October 1, 2026.