Start your Boston wine tour at Newbury Guest House and don’t miss these 15 top spots.

Think of great sips in Boston, and chowder may come to mind before wine, but the city is a major player in the East Coast wine scene. A tour of Boston vineyards, tasting rooms and some of the city’s top restaurants is a great way for novices and oenophiles alike to discover new vintages and regional gems, and to fully experience the city’s incredible food scene by pairing iconic Boston plates with the perfect glass. 

Newbury Guest House sits in the heart of the Back Bay’s famous historic brownstone district near many of the best wine spots in town, and less than a couple hours’ drive from an idyllic countryside dotted with gorgeous don’t-miss vineyards. 

Start with in-town favorites. 

The Boston Winery 

Most of Boston’s major wine happenings happen here. Wine lovers make it a regular destination for wine classes, tastings, and tours; foodies come for pairings with cheese, charcuterie, and Italian comfort food. It’s also one of the best date nights in the city. 

The City Winery Boston

It’s one of the best places for wine in Boston, with a tasting room and shop staffed with experts who’ll recommend the perfect pick. Sign up for a food and wine seminar, sample small plate food and wine pairings, check out its regular schedule of intimate concerts, and take advantage of their wine making services to create a bottle of your own to commemorate your visit.

The Urban Grape

This husband-and-wife-owned South End shop was the first in the world to use the Progressive Scale to organize wines by their body, rather than varietal or region. It hosts thrice-weekly free wine tastings for those new to the world of wine, as well as an ongoing series of grape-centric seminars and talks.

Boston Wine School

Take your wine education to the next level and learn about winemaking, wine pairings, and the business of owning a winery at this “snob-free zone” offering small interactive classes including “Crushing on Croatia”, “Is Orange Wine the New Rosé?”, “Wine 101” and “Wine, Cheese and the Pursuit of Happiness.” Founded by wine critic Jonathon Alsop, the school can also arrange special wine-focused dinners.

Now Pouring Wine Bar

Touring with someone who prefers hops to grapes? This Hub Hall hot spot also offers a great selection of craft beers. Their vast and constantly changing selection makes this an ideal place for new discoveries. Enjoy them by the bottle or by the glass or try an easy-drinking craft cocktail at this popular spot for meeting friends for drinks.

Expand your tour at top vineyards just outside Boston. 

Westport Rivers Vineyard & Winery

Sitting on 80 acres of Bristol County countryside, Westport Rivers Vineyard & Winery is the largest vineyard in New England. It’s known for the sparkling wines on which it was founded, and it would be a serious miss to visit without sampling (and purchasing) their truly excellent Farmers Fizz Sec, a Prosecco-style pour made from chardonnay grapes with a hint of Riesling.

Hardwick Winery

Don’t let the beautifully restored 18th-century mansion fool you; the winemaking at this Quabbin Reservoir vineyard is completely contemporary. You’ll find traditional reds, whites, and blushes, but the specialties here are flavorful fruit-infused wines such as Enfield Apricot or Massetts Cranberry; and for the extra-adventurous, there’s the oddly alluring Valley Asparagus. Before you go, check their website for their near-constant schedule of festivals, dinners, and wine-and-crafting workshops.

Nashoba Valley Winery

This Massachusetts wine scene heavy hitter runs its own winery, distillery, brewery, and apple-picking operation, not to mention a restaurant and regular tours, tastings and music events. Its 30-plus different varieties include pinot gris, chardonnays, and Rieslings, but if you’re looking to discover homegrown New England flavors, don’t miss their Cranberry Apple Wine and Blueberry Merlot.

Cape Cod Winery

Visit this delightful family-run winery and channel summers on the Cape with a sophisticated bottle of Vineyard Sound Sauvignon Blanc, made just a few miles from the Falmouth shore. Standouts include their expertly produced rosés and summery Mermaid Water, both delicious with the winery’s local-plate menu of shrimp cocktail and lobster rolls. Tip: If you visit before 4:00 p.m., try their Flight of the Day, an ever-changing sampling of five different wines. 

Boston restaurants with wine menus that rival the dinner menu. 

Grill 23 & Bar

This Back Bay steakhouse has an impressive 2,280-bottle selection that emphasizes wines from California, France, Germany, and Italy’s Piedmont region. Verticals such as the 1980s Caymus Cabernet Sauvignon pair especially well with the restaurant’s choice cuts of steak.

The Oceanaire Seafood Room

Boston culinary history is anchored in seafood, and you won’t find a better or more respected place in town for costal catches and wines that make them shine. Featured delicacies include grilled oysters with bacon, wild Alaska halibut, baked Gloucester haddock and anything and everything in the Oceanaire’s legendary sprawling raw bar. Expert sommeliers are happy to guide you through the award winning 250-label, West Coast-focused wine menu.

Del Frisco’s Double Eagle Steakhouse

Sleek design elements showcase the Back Bay restaurant’s award-winning selection of 2,200 wines. With stunning verticals from top-notch names such as Château Mouton-Rothschild, Opus One, and Gaja, and a team of crack sommeliers, you can’t go wrong in finding the perfect complement to legendary hand-cut steaks and fresh seafood. 

Book your stay now for Boston’s biggest wine event.

The annual Boston Wine Expo is the largest wine event in New England, and attracts experts, industry professionals, enthusiasts, and novices from across the U.S. to explore top vintages by some of the best winemakers as well as lesser-known labels from around the world. 

Tickets go on sale soon for the March 2024 Expo, which also offers classes, presentations, and seminars.

Bonus round: What to drink with iconic Boston dishes. 

The eats don’t have to be fancy to deserve a great wine pairing – just delicious. If your restaurant doesn’t come with a sommelier, here’s what to know: New England Clam chowder calls for full-bodied whites like Chardonnay or Viognier; lobster rolls are perfect with slightly acidic wines (try a Chablis, or Provence rosé); oysters love Muscadets, Fino sherries and Sancerres; and a Riesling wine with sweet notes will bring out the smokiness of that side of baked beans.

Pair the perfect wine with the perfect place to stay. 

When you stay at Newbury Guest House, one of the best mini-tours in town begins and ends just downstairs. The Bar À Vin 1855 bistro offers more than 250 different French varieties from Bordeaux and across France to pair with small plates, as well as regular tastings, classes, and special wine events. And brasserie La Voile, an authentic Cannes import, has a truly impressive wine list designed to complement its South-of-France seafood menu. Both spots have expert sommeliers on hand to assist with the perfect pairing.

Wherever your Boston wine tour takes you, Newbury Guest House is a grape place to start (sorry – we held off as long as we could). Give us a call, book your stay, and toast yourself for making a great decision.