Each winter, as Boston hunkers down beneath its gray skies and the harbor air turns to a briny chill, the Boston Harbor Hotel finds a way to warm the season. Its 37th Annual Boston Wine & Food Festival returns this year from January 23 through March 28, transforming the waterfront into a months-long celebration of global wine, culinary craftsmanship, and spirited discovery. With more than 40 events on the calendar—including pop-ups, master classes, winemaker dinners, and extravagant reserve experiences—the festival invites locals and travelers alike to turn winter into an excuse to indulge.
The festival, one of the country’s longest-running wine celebrations, unfolds amid the hotel’s newly refreshed harbor view spaces, where executive chef David Daniels and festival director Nick Daddona curate a mix of refined dinners and high-energy tastings. “We always want to surprise guests,” Daddona says. “This year feels like a journey—something for the collector, the sipper, the cocktail lover, and everyone in between.”
Anniversary Inspired Dinner
The program includes several standout debuts. The President’s Reserve Dinner, created in honor of the 250th anniversary of the signing of the Declaration of Independence, offers a historical spin on wine culture. Guided by wine authority Kevin Zraly, the evening explores the bottles beloved by six U.S. presidents— from Jefferson’s affinity for Burgundy to Reagan’s devotion to California Cabernet—paired with a commemorative menu from Chef Daniels. Equally compelling is the new Mezcal Master Class, a deep dive into agave traditions that spans wild and cultivated plants, artisanal roasting methods, and regional distinctions. The hotel also introduces a Macallan Whiskey Master Class, plus an Art of the Espresso Martini session dedicated to the drink that refuses to relinquish its spotlight.
An Array of Pop-ups
If the festival is known for one thing, however, it’s the breadth of its experiences and nowhere is that more evident than in its lineup of pop-up events. Designed as approachable, high-energy tastings, these one-hour sessions allow guests to explore new regions and techniques without committing to a formal multicourse dinner. They also tend to be among the first events to sell out. The season’s pop-ups trace a global arc:
Gaucho Cowboys (Jan. 29) brings the spirit of South American ranch culture to Boston, with tastings of Malbec, Cabernet, and blends from Argentina and Chile alongside traditional gaucho cuisine. Provence Pop-Up with Domaines Ott (Feb. 26) provides a burst of southern French sunshine in the middle of winter, with a tasting of Ott’s signature rosés, whites, and reds paired with coastal bites. Rioja Pop-Up with Bodegas Martínez Lacuesta (Mar. 5) highlights the region’s evolving identity through a curated flight led by estate director Oscar Alvarez Gárate.
Women & Cocktails (Mar. 12) brings together two of Boston’s most respected bartending figures, Misty Kalkofen and Kitty Amann, for three cocktail demonstrations paired with bites from Chef Chelsea Fedora. Wines of Loire Pop-Up with CoulyDutheil (Mar. 19) spotlights Chinon’s benchmark Cabernet Franc and Chenin Blanc, revealing how limestone soils shape their structure and freshness. Barolo Pop-Up with Scarzello (Mar. 26) offers a focused exploration of traditional, small-production Nebbiolo from one of Barolo’s most admired family estates. These pop-ups, with their blend of energy and education, represent the festival at its most accessible—and its most fun.
Marquee Dinners
Of course, many guests come to the festival for its marquee dinners. This year’s winemaker lineup reads like a who’s who of global wine royalty: Champagne Louis Roederer, Cakebread Cellars, Joseph Phelps Vineyards, Beringer, Sequoia Grove, and top Pinot Noir producers including Hirsch, Peay, and Littorai. The interactive Judgement of Paris Dinner, presented by Delta Air Lines, remains a fan favorite, inviting diners to vote—flag in hand—between French and Californian pairings. The ever-popular Battle of the Cabs, offered in both January and February, showcases the world’s most beloved red varietal with flair.
The festival’s most extravagant offering returns as well: the Grand Cru Tasting with Domaine de la RomanéeConti, an ultra-private evening priced at $38,500 for up to eight guests. Held in the hotel’s Presidential Suite, the experience includes a sommelier-led tasting, six-course dinner, overnight accommodations, and brunch on a sprawling terrace overlooking the harbor. It’s bucket-list indulgence at its most memorable. With special festival room rates starting at $310, the hotel makes it easy to turn any event—whether a one-hour pop-up or a six-course Champagne dinner—into a mini winter getaway.
Whether you’re a seasoned taster or simply looking for a warm, spirited reason to venture out this winter, the Boston Wine & Food Festival remains one of Boston’s most enticing seasonal traditions—an invitation to sip, savor, and celebrate the flavors of the world without ever leaving the harbor.