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Winter in Boston: Luxury Stays, Dines, & Activities | ICONIC LIFE

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Winter in Boston: Luxury Stays, Dines, & Activities

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Learn about the best places to stay, dine and play in Boston during the winter season.

Boston is the most European city in the U.S. seamlessly blending the old with new. Winter in Boston means the return of snow-frosted streets, soft flannel shirts, fur-lined boots, warm glows of fireplaces and comfort food and sips.

Boston is a luxurious yet unpretentious destination. Here are some spots to sip, skate and stay this winter in Boston.

Stay

A room with a view—and a flue. Winter guests will find a curated hearth-side menu and expert services of a Fireplace Butler at The Newbury Boston, a snowball throw from the snowy Public Garden across the street.

Guest rooms are spacious and elegant with floor-to-ceiling window views of the Boston Public Garden. But for the Newbury Boston stay during the winter, it is all about the hotel’s 42 wood-burning Fireplace Suites, with separate living and sleeping areas and deluxe bathrooms.

Choose from a menu of wood varietals including birch, cherry, oak and the sweet New England maple. The hotel’s Fireplace Butler will take care of the rest. Also, order fireside nibbles like traditional Poutine, a S’mores Kit or cider donuts and sip hot apple cider or house-bottled cocktails that taste like the Campfire—a smoky pour with Mezcal, chocolate mole bitters and marshmallow syrup. 

The fireside ambiance is common at the Newbury, with two cozy fireplaces in the 1920s inspired “Street Bar” lounge and the famous library, warm relaxation during the cold winter in Boston has never been more accessible. 

Also, the Contessa restaurant dazzles on the rooftop—perfect for views of snow-brushed treetops and twinkling stars on a winter night in Boston. The polished, exclusive restaurant shows off an Italian trattoria-inspired hearty menu for winter nights in Boston (think: daily imported burrata and spicy lobster cavatelli).

Boston’s dazzling Seaport District is home to spectacular hotels including The Seaport Hotel Boston, the first hotel that came on the scene in the Seaport District many years ago and is still the heartbeat of it all. With sunrise views over Boston Harbor and Boston Fish Pier from many of the 428 guest rooms– the perfect scene to watch the snowfall this winter in Boston, this prestigious hotel is a beauty.

The light-filled guest rooms are decorated in blue and orange pastels and feature Seaport signature pillow top mattresses, another thoughtful feature, guests can choose from a pillow menu, too. 

The Seaport Hotel is also one of the greenest hotels in Boston with on-site apiaries and herb gardens. Even dogs are pampered here—there’s a grassy lawn area for traveling pets.

Winter in Boston means warming up by the fireplace at the hotel’s TAMO restaurant and digging into Boston’s bests like a bowl of New England clam chowder. Guests can also relax in the heated indoor swimming pool at the hotel’s Wave Health and Fitness—the largest hotel fitness club in Boston with saunas, steam rooms and fitness classes. This hotel is a great Seaport spot to take in the falling snowflakes during the cold winter months in Boston.  

For nearly a century, the Ritz-Carlton Boston has been the epitome of luxury, charming Boston Brahmins with unparalleled service for most of the century at its former address on the corner of Newbury (where the Newbury Hotel now stands). The Ritz moved to its current spot on Avery Street near the Theater District about ten years ago.

The Ritz’s guest rooms were $15 per night when the hotel first opened in 1927, and although that rate is a bygone era, the refurbished hotel’s guest rooms and suites show a level of opulence that make the price increase worth it. Suites boast expansive views that overlook the Boston Common—which is a popular spot in winter in Boston for sledding. And guests have privileges at the adjoining Equinox Sports Club if sledding doesn’t suit your fancy.

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The Ritz-Carlton Club® Level (concierge, breakfast, hors d’ oeuvres, spirits, sweets) is a respite on a winter day in Boston. The retro-chic, dimly-lit Avery Bar, is the spot to warm up after a day of exploring the snow-covered parks and cobblestoned streets of the Freedom Trail. Classic cocktails are served in front of the marble fireplace in the spacious room off the lobby—toast the 1920s with the signature 1927, a cocktail poured with El Dorado 12 Year Rum, RitzCarlton Custom Iced Tea Blend and lime or indulge in the Avery Vesper made with Avery Gin, Absolut Elyx, Lille Blanc and lemon.

Winter in Boston the Mandarin Oriental Hotel

Diamonds and stars define the elegant Mandarin Oriental Boston, and guests receive a lovely Boston winter greeting at check-in—a cup of the luxury hotel’s signature tea. The 148-room/suite Mandarin, with its perfect Back Bay address and exceptional service, is a skip from the toniest of Newbury Street boutiques where Boston winter strolls are magical.

The guest rooms, a mix of Art Deco and modern influences, feature plush lounge seating in front of huge windows with pretty garden or city views. The hotel has been awarded AAA Five-Diamonds and Forbes Five-Stars, and the spa is one of the reasons. One perfect Boston winter warmup treatment is the popular lava stone therapy inspired by Native American rituals using heated stones to create energy.

There’s also celebrity chef Gordon Ramsay’s namesake street-level restaurant, where he turns up the heat and is popular with locals and visitors—the perfect sip for Boston winters is the One Last Kiss, poured with Tozai Snow Maiden Nigori Sake! Campari, Lychee, Moscato d’Asti, lemon, raspberry and Peychaud bitters. 

The Boston Harbor Hotel is a 232-room/suited Forbes Five-Star & AAA Five Diamond beauty with impressive window views that frame the Boston winter scenes—like sea smoke rising from Rowes Wharf on Boston Harbor on frigid days or clear winter sky views of the city skyline and the Rose Kennedy Greenway.

Rowes Wharf Sea Grille is where the hotel’s ICONIC grand afternoon tea is served—vanilla bean scones, warm gruyere fondue and the signature prosecco-laced green tea sparkler are special winter-in-Boston treats—and afterall, it is this harbor that is celebrating the 250th anniversary of the Boston Tea Party, so let the tea steep. 

Winter in Boston also calls for slinking into a leather chair at the hotel’s Rowes Wharf Bar, ranked by Forbes as one of the best hotel bars in the world. The Champagne Cocktail is a special sip created with a brown sugar cube, soaked with bitters and set afloat in Moët & Chandon Champagne. 

There is also something special about a swim when it’s snowing outside— the hotel has a warm 60-foot indoor pool, as well as a state-of-the-art fitness center with a sauna and eucalyptus-infused steam room, perfect antidotes to cold winter days in Boston.

Eat 

There are many worthy A-list restaurants in Boston. As the culinary scene continues to evolve in a town known for its lobster, chowder, baked beans and Boston cream pie, here are just a few don’t-miss spots.

Winter in Boston, wood hill pier 4

Woods Hill Pier 4 is the splashy Seaport District’s pearl is this refined waterfront restaurant, a sprawling space with floor-to-ceiling windows for watching bundled-up passersby strolling along the Boston Harborwalk. Expect gorgeous dishes of organic, non-GMO and locally-sourced products, fresh-caught seafood and meat from a partner farm, the Farm at Woods Hill in Bath, New Hampshire. 

Winter menu standouts include Crispy Lamb Ribs with Urfa Pepper and Red Wine Glaze, Sprouted Sunflower Seed Risotto and Woods HIll Farm Glazed Pork, Squash, Sassafras, Spigarello. Even the cocktail menu splashes light on the restaurant’s commitment to local ingredients: The Farmers Whim is a rotating cocktail featuring local products—this winter, it’s the farm’s elderberries that star in a cocktail made with Sipsmith Lemon Drizzle Gin, a housemade Elderberry Cordial, organic cane sugar, fresh squeezed lemon juice and egg white.

Also, a celebratory winter in Boston dish served here is the Pier 4 Caviar Service served with warm popovers and a side dish of sherbet sunsets over the harbor. 

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France meets Boston at this joie-de-vivre ICONIC restaurant, Bistro du Midi, across from Boston’s Monetesquè Public Gardens—so again, you don’t have to travel to Europe to experience the continent’s wintry best and refined elegant French service.

A bowl of the Winter Squash Soup and Vanilla Bean Crème Brûlée are perfect après-skate treats. The lively and popular street-level bistro is perfect for a casual meal (Croque Monsieur, Moules Frites, Seared Tuna Nicoise…) while upstairs in the dining room is a more sophisticated eating experience with gas fireplaces and Southern French cuisine (Bouillabaisse du Midi, Wild Mushroom Tarts, Foie Gras Torchon….).

Make sure to snag a coveted window seat for warm views of quintessential winter-in-Boston scenes in the frosty Public Gardens. 

Yvonne’s is a high-end social dining spot with a modern supper club vibe. Every proper Bostonian knows that it is the reincarnation of much-loved Locke-Ober restaurant which debuted in 1901 and had quite a following. Today, it is still the place to see and be seen and popular with the celebrity crowd.

The reimagined space, which opened in 2016, is all about moody lighting, chandeliers and banquettes. Yvonne’s is a hybrid of the Middle East, the Mediterranean, Europe and local cuisines like a gorgeous plate of Moroccan hummus and baked Duxbury oysters with lobster porcini cream.

Finish the meal with a showstopper, the  classic and adored Baked Alaska that’s starred on menus at some of the country’s best restaurants for over a century. The cocktail scene here features large formats like the Heartbreakers, a cocktail made with spicy tequila, mezcal, pomegranate, orgeat, lime and angostura is perfect for winter in Boston visits.

The Circus Charlie, a cocktail with brownie-infused Bourbon, coffee-infused Punt e Mes and marshmallow will satisfy your sweet tooth after a hearty meal. 

Play 

Where do we begin to tell the story of the love for Harvard Square in the winter, just across the Charles River in Cambridge. When the snow falls, reenact the ICONIC scene out of Love Story where Ryan O’Neal and Ali McGraw play in the snow and make snow angels and snowmen in the Harvard Yard. Visit Henrietta’s inside the smart-looking luxury Charles Hotel for breakfast or lunch, and hit the book stores and shops that are in Harvard Square, always a busy spot with students and professors.

Winter in Boston, Frog Pond

Bundle up, it’s time to skate at Frog Pond in the beautiful Boston Common, with the city skyline peeking through the snow-dusted tree branches. The setting is intimate and romantic and is pure Boston charm. You’ll want to wait until the sun sets for a night skate under the dazzling skyline.

The pond closes at 10 p.m. on weekends and 9 p.m. on weekdays. And even if skating isn’t in your repertoire or skill set, you’ll want to visit to experience Boston’s beloved winter tradition. 

Boston’s newest attraction is the View Boston Observation Deck that crowns the top of the Prudential Tower. It gives visitors indoor and outdoor panoramic views of the city, has an open-air roof deck and a pair of restaurants, too—and on a clear day you can see forever.

There’s a 22-seat bar that faces the windows for a cocktail and stunning views. For a perfect taste of winter in Boston, order the One Night in Boston sip, a nice nod to the city, made with Baijiu Tequila, Cointreau, Orgeat, Campari, orange juice, lime juice and coconut water, pair that with baked clams and a lobster roll, of course.

To escape the cold, and for an ICONIC Boston treasure, visit the Isabella Stewart Gardner Museum. The Isabella Stewart Gardner Museum opened in 1903 and is home to some of  the most sought out pieces of art and features  incredible interior and exterior gardens and greenhouses—glorious on a winter day—and a lovely Courtyard.

The museum is also a spot for musicians and performers throughout the year. If you’re craving a bite to eat, Cafe G is the perfect spot for Warm Banana Bread Pudding and Local Clam and Chorizo Rigatoni.

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