The Ultimate Holiday Guide to Eating, Drinking, and Merrymaking in Boston

Where to find the best holiday cocktail pop-ups, hot chocolate bars, Santa teas, highly decorated restaurants, and ski-lodge-inspired winter patios in and around the city in 2023.

Christmas cocktails are served in T-rex-shaped glassware and surrounding by Christmas decor, like fake trees and ornaments.

“Rudolph’s Replacement,” a 2023 Miracle pop-up cocktail. / Photo by Melissa Hom

With winter on the horizon and stores already dusting off their Christmas playlists, it’s clearly the season for holiday festivities. What does this mean in the Greater Boston hospitality scene? For many restaurants, bars, and hotels, it’s just about time to break out the ornaments, lights, wreaths, and garland. From over-the-top décor to holiday cocktails, from afternoon teas with guest appearances by Santa to hot cider at a giant market, there’s a lot going on these days.

Below, we’re tracking holiday beverage pop-ups (cocktails, hot chocolate, tea, etc.); venues that get really decked out for the holidays; and even a few ski-lodge-inspired winter pop-ups that’ll keep that festive feeling going into the new year. (You may also be interested in our guides to holiday lunches, cozy fireplaces, and hot chocolate, each freshly updated for 2023.)

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Holiday and Winter Beverage Pop-ups

From Santa-themed cocktails to luxurious hot chocolate

A white mug is full of hot chocolate and surrounded by sweet treats. Bottles of Baileys and Maker's Mark are visible in the background.

Hot chocolate at “Avery Bar Chocolat.” / Photo courtesy of the Ritz-Carlton, Boston

Avery Bar Chocolat

Hot chocolate bar

On Saturday afternoons and evenings throughout the holiday season, the Ritz-Carlton’s swanky Avery Bar—complete with a cozy fireplace!—becomes the ultimate hot chocolate destination. Relax over a warming mug while choosing among decadent toppings—from candy cane shortbread cookies to caramel whipped cream—and indulging in pastries and sweets while you sip. Also, bring the kids: Adults can sip a richer cup (with the optional addition of a spirit or cordial) made of a blend of milk and dark chocolates, while the little ones enjoy a lighter, easier-drinking style.

The Ritz-Carlton, Boston, 10 Avery St., Downtown Boston, 617-574-7100,

Hot Chocolate, Cocktails, and Tea at the Four Seasons

This hotel is doing all the holiday beverages

At Four Seasons One Dalton Street, Boston, the team is hitting pretty much all the holiday season beverage notes. There’s the lobby chocolate bar, for one, with bonbons, cookies, and mugs of hot cocoa with toppings like peppermint bark and marshmallows; catch it from November 27 through January 1 (3 p.m. to 6 p.m. weekdays and noon to 6 p.m. weekends). At the hotel’s cocktail lounge, Trifecta, find gold-themed winter décor and a “12 Days of Cocktails” holiday menu with creative glassware and tableside drink-making. Despite the carol-inspired name, the holiday menu is available for the entire month of December; definitely make a reservation. Also at Trifecta—and with reservations encouraged and available at that same link—the afternoon tea service is holiday-themed starting December 1 (served Friday, Saturday, and Sunday). Treats will include orange ginger petit fours and white chocolate mocha opera cakes, paired with seasonal teas and liqueurs.

1 Dalton St., Back Bay, Boston, 617-377-4888,

Three outdoor dining igloos are on a twinkle light-bedecked patio at night.

“Inngloos” at the Inn at Hastings Park. / Photo by Paige Harding/PAH Photography

The Inn at Hastings Park’s “Christmas Tea with Santa”

Family-friendly afternoon tea—optionally in an igloo

Lexington’s acclaimed Inn at Hastings Park offers a lovely Saturday high tea all year, but on December 9 and 10, it’s a special holiday edition for the whole family, including: tea, cocktails, and towers of sweet and savory bites for the grownups; tea or hot cocoa, snacks, and activities for the kids; and, of course, pictures with Santa for everyone. Seating is available inside the Town Meeting Bistro or, for even more fun, inside an “Inngloo.” Reserve via Resy: December 9, December 10.

Town Meeting Bistro at the Inn at Hastings Park, 2027 Massachusetts Ave., Lexington, 781-301-6655,

A pale pink cocktail with foam and blue sprinkle garnish sits on a blue surface, surrounded by Hanukkah gelt and a dreidel.

A Maccabee bar cocktail. / Courtesy photo

Maccabee Bar

Hanukkah-themed cocktail and snack pop-up

A Manischewitz-infused Aperol “schvitz”; a vodka sour with jelly doughnut notes; an apple brandy sour that tastes like a latke—oy vey! Founded in 2018, Boston bar star Naomi Levy’s Hanukkah-themed cocktail bar is back this year. It’s currently slated for a December residency at the Charles Hotel’s Noir, but keep an eye out for additional locations locally and beyond. Can’t decide on a drink? Take a chance and spin the dreidel! (Levy hasn’t announced the full 2023 menu yet, but there will be snacks involved as well, including latkes from the Noir kitchen and sufganiyot—jelly doughnuts—from Lionheart Confections.) Limited reservations available via email ( but plenty of space for walk-ins.

The Charles Hotel, 1 Bennett St., Harvard Square, Cambridge, 617-661-8010 (Noir),

A bar is decorated with Christmas lights, a light-up palm tree, and a giant Santa figure who looks dressed for a beach and holds a tiki-style cocktail.

Shore Leave, decorated for the annual Sippin’ Santa pop-up. / Photo by Reagan Byrne

Miracle and Sippin’ Santa

Christmas-themed cocktail pop-ups

Christmas-themed cocktail pop-up Miracle and its Christmas-meets-tropical spinoff, Sippin’ Santa, are taking up residence at several Boston-area venues yet again this year in a fun, kitschy tradition that got its start in New York City in 2014. The pop-ups have since franchised out around the world, with Boston-area bars participating since 2017. Head to the Hotel Marlowe in Cambridge or Mystic Station in Malden from late November through late December for Miracle’s over-the-top décor and glassware, featuring silly but tasty drinks with names like “Grandma Got Run Over by a T-Rex.” Sippin’ Santa, meanwhile, returns to Shore Leave in Boston’s South End to delight with rummy “Kris Kringle Coladas” and lots more.

Multiple locations, and

Santa’s Cantina at Loco Fenway

Drinks, vibes, and holiday lunch

In addition to offering a holiday lunch prix fixe menu throughout the season, Loco Taqueria & Oyster Bar is turning its enormous new-ish location in the Fenway into a winter wonderland full of themed décor. Swing by in November and December to enjoy the ambiance (including a Christmas tree made of tequila bottles) and a special holiday cocktail menu. Stay tuned for drink details.

61 Brookline Ave., Fenway, Boston, 857-277-0769,

An outdoor holiday market in the middle of the city features lots of white lights and lots of people dressed in warm clothes. There's a big Christmas tree and curling lanes visible.

Snowport. / Photo by Alexander Pickering


Giant holiday market with plenty to drink

The Seaport District’s annual holiday market is back for its fifth year, and in addition to a ton of vendors, Betty the Yeti sightings, iceless curling, and other fun, there are numerous opportunities to drink wintery beverages. The setup includes four holiday-themed bar areas (Jingle Bar, Dizzy Dreidel, and more); watch for options like hot mulled cider from Downeast Cider and a variety of other cocktails (some served hot). There’s plenty of food to go with those drinks, include melty cheese in a surprisingly high number of forms.

Snowport, 100 Seaport Blvd., Seaport District, Boston,

A few cocktails with Christmas-y garnishes, like rosemary and cranberries, sit in front of a Christmas tree.

Cocktails from the pop-up holiday bar at the Mandarin Oriental. / Photo by Leise Jones

Triple Eight Distillery Pop-up Bar at the Mandarin Oriental, Boston

Nantucket whisky, live jazz, and more

As of November 28, the Mandarin Oriental’s lobby will be decked out in Christmas lights and other festive décor, including a tree. The season’s events and offerings include live jazz, hot cocoa, and space by the crackling fireplace, not to mention a pop-up cocktail bar featuring Nantucket’s Triple Eight Distillery, and in particular, its single malt whisky, the Notch. Operating Thursday through Saturday from 4 to 7 p.m., November 30 through December 30, the bar offers holiday cocktails, whisky flights, and a handful of snacks.

Mandarin Oriental, Boston, 776 Boylston St., Back Bay, Boston, 617-535-8888,

Good Holiday Vibes

These venues really deck the halls

Delux Cafe, South End

This casual South End haunt always looks like December with its year-round Christmas lights and convivial vibe. Swing by the eclectic spot for a warm dive-bar feel, $5 cans of Schlitz, and comfort food. (We’re big fans of the bathroom, too.)

100 Chandler St., South End, Boston, 617-338-5258,

An elegant steakhouse bar area is decorated with a lit-up Christmas tree.

Grill 23 & Bar always decks the halls. / Courtesy photo

Grill 23 & Bar, Back Bay

The 40-year-old steakhouse always looks grand for Christmas: think wreaths, a big tree, and other elegant touches. Check out the special holiday lunch on select dates in December, or make a reservation for a fancy steak dinner anytime. We also whole-heartedly recommend a post-work visit to the bar for a drink and dessert (like the signature coconut cake or classic chocolate chip cookies).

161 Berkeley St., Back Bay, Boston, 617-542-2255,

The tall atrium of a hotel lobby features full-sized Christmas trees dangling upside down.

The upside-down tree display at the Liberty Hotel. / Courtesy photo

The Liberty Hotel­, Beacon Hill

Is it really December if you haven’t gazed up in awe at the Liberty Hotel’s upside-down Christmas tree display in its tall atrium? It’s a good opportunity to plan a visit to one of the hotel’s restaurants or bars, including Lydia Shire’s Italian-inspired mainstay, Scampo, or Clink, which is offering a holiday lunch menu.

215 Charles St., Beacon Hill, Boston, 617-224-4000,

A black lab wearing a santa hat sits in a hotel lobby in front of a giant Christmas tree.

On your way to Oak Long Bar + Kitchen, you might spot Cori Copley, the Fairmont Copley’s “canine ambassador,” pictured here in front of the hotel’s tree in 2022. / Photo by Kataram Studios

Oak Long Bar + Kitchen, Back Bay

Luxurious Back Bay hotel Fairmont Copley Plaza really does it up come Christmastime: You’ll see items like a giant Christmas tree and an array of dazzling festive wreaths. The vibes spill into the hotel’s gorgeous restaurant, Oak Long Bar + Kitchen—which is open on Christmas Day, in case you’re looking to feast on lobster Thermidor or a yule log dessert.

Fairmont Copley Plaza, 138 St. James Ave., Back Bay, Boston, 617-585-7222,

A restaurant with shiny red booths is decorated for Christmas with a tree and tons of ornament-bedecked garlands covering the ceiling.

Holiday decorations at the Venetian in Weymouth. / Photo by Paige Harding/PAH Photography

The Venetian, Weymouth

Head south of the city to dine among over thousands of ornaments and twinkling lights, not to mention garlands, trees, and other Christmas-y magic, installed in partnership with local florist Beach Plum Floral Design. The spacious Italian restaurant has completely transformed into a holiday wonderland—and it’ll remain that way through the end of January, in case you want to keep the Christmas feelings going post-December. Reservations encouraged but not required, and this is a family-friendly spot. The standard lunch and dinner menus will be served, but watch for seasonal specials and festive treats.

909 Broad St., Weymouth,

Wusong Road, Cambridge

Every inch of this tiki bar and restaurant is filled with eye-catching décor year-round. Visit from late November through late December, though, and you’ll find even more: “Wusong Wonderland,” as the team calls it, returns this year with plenty of Christmas-y accents, seasonal tiki mugs, and other surprises.

112 Mt. Auburn St., Harvard Square, Cambridge, 617-528-9125,

Gingerbread Housemaking

Time to break out those design skills

Decorated gingerbread houses are lined up in front of a brick wall.

Gingerbread decorating at A&B Kitchen and Bar. / Courtesy photo

A&B Kitchen and Bar

Swing by A&B in Boston’s West End for gingerbread house decorating on December 8 (4 p.m. to 10 p.m.; reservations required—look under “experiences.”) For $60 a couple, you’ll get a pre-built gingerbread house with icing, candies, and two glasses of champagne ($50 without the champagne). Email the restaurant to inquire about pricing for larger groups.

115 Beverly St., West End, Boston, 857-449-2251,

Eastern Standard

Haven’t checked out Eastern Standard 2.0 yet? Boston’s favorite recently reborn brasserie is hosting “Gingerbread Standard Construction”—a tradition the team attempted to begin in 2019 before the pandemic and closure prevented future occurrences. For $150, your table of four gets a fresh-baked, constructed house, ready for you to decorate. Choose your tools from the decorating station—featuring over 100 pounds of candy—and stay refreshed with hot cocoa and spiced apple cider. Additional drinks and snacks will be available for purchase. Don’t forget to bring a toy to donate to Christmas in the City; participating tables will receive a pretzel plate as thanks. As of press time, tickets remain for December 2 and 9.

775 Beacon St. (in the Bower), Fenway/Kenmore, Boston, 617-530-1590,

The Langham, Boston

This family-friendly, Paddington-themed gingerbread workshop takes place on December 16 with seatings at noon and 3 p.m. Priced at $155 per gingerbread house (for up to two kids), the ticket also includes a limited edition Paddington diner set, a hot chocolate and candy bar, and photos with Santa. Those over 21+ can visit the cash bar.

250 Franklin St., Downtown Boston, 617-451-1900,

Wintery Pop-ups

Turning restaurant patios and courtyards into food-filled ski lodges

Après at Deck 12, Seaport District

Who says rooftops are just for summer? For the second year, Yotel is turning its popular indoor-outdoor roof deck into the mountain lodge of your ski-themed dreams: heated gondola-like spaces, Adirondack chairs, and such—not to mention stunning Boston skyline views. A special food and drink menu will be available, with winter-themed cocktails, hot cocoa, and plenty of comfort food.

Yotel Boston, 65 Seaport Blvd., Seaport District, Boston, 617-377-4747,

A brown cocktail is in a short glass decorated with the silhouette of a ski lift. Christmas lights and fake trees surround the glass.

A Gufo cocktail from the Alpine Après winter pop-up. / Courtesy photo

Alpine Après at Gufo, Cambridge

New Italian restaurant Gufo is similarly thinking of mountains this winter, transforming its heated and enclosed patio space into a cozy destination that draws inspiration from 1970s Italian Alps ski lodges. Open on Friday, Saturday, and Sunday evenings, the first come, first served patio will include a menu to go with the theme. You’ll find comforting dishes like alpine pizza with prosciutto crema, potatoes, fontina, and rosemary; soft polenta mushroom ragu; and baked gnocchi with fontina, breadcrumbs, and truffle; not to mention desserts like a cookie platter and panettone. Hot cocktails and other seasonal specials will amp up the menu. (Contact the restaurant to inquire about holiday parties and other private events in the space—it’s available for bookings the rest of the week.)

660 Cambridge St., East Cambridge,

A restaurant is decorated with a ski lodge-style theme. A life-sized bear holds a sign welcoming people to the venue.

The Lodge at Publico returns this winter. / Courtesy photo

The Lodge at Publico, South Boston

Starting December 7, the Southie restaurant Publico will again turn its expansive inner courtyard into a ski-chalet-inspired space for the winter. This year will be extra special as the Lodge will play host to the Cisco Brewers beer garden, whose Seaport location is hibernating for the winter. (Don’t worry; Publico is still offering its popular “shot-skis”—the best way to do shots with your friends—and cocktails, too.) Hungry? There’ll be a menu of made-to-share comfort food.

11 Dorchester St., South Boston, 617-622-5700,

Igloo Dining

More cold-weather outdoor dining options

For igloo and other heated outdoor dining options in and near Boston, check out our winter outdoor dining guide, updated for 2023. Below, find a couple options farther outside of the city:

The Inn at Hastings Park

This boutique hotel’s igloos—sorry, inngloos—aren’t just for Christmas tea with Santa (see above.) Warmed by a faux-fireplace heater, and with blankets and hand warmers available, each igloo seats up to six for a private lunch, brunch, dinner, or tea, featuring menus from the inn’s Town Meeting Bistro. Think seasonal New England fare: lamb neck Yankee pot roast, roasted acorn squash, and such. Children can be accommodated, as can dietary restrictions. Book online or by phone; a $120 fee is required when the reservation is made.

2027 Massachusetts Ave., Lexington, 781-301-6655,

A see-through dining igloo sits atop a restaurant rooftop with city skyline views as snow falls.

A rooftop igloo at the Mercantile. / Courtesy photo

The Mercantile

Finding yourself in the Worcester area this winter? Head to the Mercantile for rooftop igloos with city views. The heated dining spaces come equipped with Bluetooth speakers, and you can enjoy the full dinner and cocktail menu. (The restaurant describes its food as “New American tavern cuisine”—think brick-oven pizzas, hearty salad and rice bowls, sandwiches, and comfort-food entrees like mac and cheese and steak tips.) Watch for igloo reservations to open up in early December via OpenTable.

2 Mercantile St., Worcester, 774-389-5180,

Portions of this guide appeared in the print edition of the December 2023/January 2024 issue with the headline “It’s the Most Wonderful Lunch of the Year.”