Discover the Magic of a Boston Winter Getaway
When the temperature drops, Boston transforms into a picturesque, snow-dusted wonderland that captures the true essence of New England charm. Stripping away the heavy summer crowds, winter reveals a cosy, intimate side of the historic city. From glowing cobblestone streets to world-class indoor warmth, Boston in winter is the ultimate seasonal holiday.
Start your morning strolling the gas-lit streets of Beacon Hill. The snow-covered brick townhouses and historic alleys offer a postcard-perfect setting. Just a short walk away, you can lace up your skates at the iconic Boston Common Frog Pond. Gliding across the ice, surrounded by twinkling holiday lights and the city skyline, is a quintessential Boston tradition.
When you need to escape the crisp winter air, Boston’s world-class cultural indoor institutions offer cosy refuge. Spend a warm afternoon exploring the stunning, Venetian-style courtyard at the Isabella Stewart Gardner Museum, or admire the masterworks housed in the Museum of Fine Arts. For a truly unique seasonal experience, you can even book a heated Boston Harbour Cruise to view the majestic city skyline while sipping hot cocoa from the comfort of a warm observation cabin.
Winter is also the prime season to experience the city's legendary sports culture. Feel the electric energy of local crowds by catching a thrilling Boston Bruins hockey game or a Celtics basketball game at the vibrant TD Garden.
No winter holiday is complete without incredible food. Warm up in the historic North End, Boston's famous Italian neighbourhood, where you can indulge in hearty, handmade pastas and world-renowned fresh pastries. For a modern twist, head to the bustling Seaport District to explore Snowport, a festive winter village packed with local craft vendors, interactive games, and unique culinary treats.
Whether you are looking for a romantic weekend escape or a fun-filled family holiday, Boston delivers a magical winter experience like no other. Pack your favourite winter coat and discover the historic charm, seasonal cheer, and unforgettable warmth of this classic New England city.
Boston Winter Wonderlust Package
Winter City Break
Return direct flights to Boston
Arrival & departure Boston private airport transfers
3 Nights at the 5* Intercontinental Boston
From £1,149 Per Person based on 2 sharing
Other packages, hotels and durations are available, call us on 0844 80 444 80 to book
How to spend your weekend City break in Boston this Winter...
Day 1: Historic Beacon Hill & Frostival Lodge
Morning:
Stroll the Snowy Common & Beacon Hill
- Start your morning at Boston Common. Grab a warm beverage and walk through the historic park before heading into neighbouring Beacon Hill.
- Wander down the gas-lit, cobblestone alleys, making sure to snap a photo of Acorn Street, which looks uniquely beautiful framed by winter snow.
Lunch:
Hearty New England Comfort
- Warm up at The Dubliner Pub near Government Center for a buzzing, authentic Irish atmosphere and hearty comfort food to fuel your walking.
Afternoon & Evening:
The Frostival Lodge
- Head into Back Bay to experience Copley Square, which transforms into an immersive winter playground for Frostival.
- Spend your afternoon and evening inside the Frostival Lodge (Open daily 11:00 AM – 9:00 PM; Free admission). Furnished completely like a ski chalet by Wayfair, you can hang out in cosy lounge areas, play giant board games, or try outdoor curling and fire pits. Grab dinner right inside the lodge.
Day 2: North End Food & Frostival Ferris Wheel
Morning:
Italian Comfort Food in the North End
- Walk off the winter chill by exploring Boston's historic Italian neighborhood. Stop at iconic pastry shops like Modern Pastry or Mike's Pastry for cannoli.
Lunch:
Classic Italian Fare
- Sit down for a classic, cozy lunch at Massimino's in the North End for exceptional chicken parmigiana.
Afternoon:
Quincy Market & The Rose Kennedy Greenway
- Walk over to Faneuil Hall and Quincy Market to browse the indoor stalls.
- Next, head to the Rose Kennedy Greenway for Frostival’s second major winter installation: the 75-foot Frostival Ferris Wheel. For just $4 per ticket, ride the wheel to get breathtaking, crisp winter views over the Boston skyline and the harbor waterfront.
Dinner:
Fresh New England Seafood
- Keep to the coastal vibe by heading down the street to The Banks Fish House for high-end local seafood—their lobster dishes are a must-try.
Day 3: Ice Skating, Museum Magic & View Boston
Morning:
Ice Skating at Frog Pond
- Embrace the classic Boston winter tradition by going ice skating at the Frog Pond on Boston Common. It's a picturesque winter scene right in the center of the city.
Lunch:
Quick Grazing at Time Out Market
- Take the Green Line T transit over to the Fenway neighborhood and head to Time Out Market. It’s an indoor food hall perfect for grazing, featuring everything from local tacos to craft burgers under one warm roof.
Afternoon:
Indoor Cultural Escape
- Escape the cold inside one of Boston's world-class museums. Choose between the expansive Museum of Fine Arts (MFA) or the breathtaking, Venetian-style winter courtyard of the Isabella Stewart Gardner Museum.
Evening:
Views from the Top
- Cap off the night back in Back Bay at View Boston, located at the top of the Prudential Center. The 52nd-floor indoor observation deck gives you panoramic, 360-degree night views of all the areas you've explored.
Day 4: Seaport’s Winter Wonderland
Morning:
Discover the Seaport District
- Spend your final day exploring the trendy, modern Seaport District. Walk along the Boston Harborwalk if the weather permits, taking in the crisp maritime air.
Lunch:
Farm-to-Table Luxury
- Enjoy a cozy, waterfront lunch at Woods Hill Pier Four, known for its high-quality farm-to-table dining and spectacular pier views.
Afternoon:
Snowport Winter Village
- Tie your trip together by visiting Snowport, the Seaport's massive seasonal winter village footprint. While its holiday market winds down earlier in winter, the space continues to offer winter games, outdoor iceless curling lanes, festive photo backdrops, and large heated tents with local food vendors.
Evening:
Cosy Farewell Drinks
- End your winter getaway by toast-ing your trip with creative cocktails before heading to the airport to take your flight home.
Embrace the Magic of Winter at Boston Frostival
Late November - February
Forget hibernation—winter in Boston has been completely reimagined!.
If you are seeking the ultimate cold-weather getaway, look no further than Boston Frostival. This spectacular, season-long celebration transforms the historic city into an interactive winter playground, blending classic holiday traditions with thrilling new attractions.
The magic kicks off in the skies above the iconic Boston Common, where dazzling, holiday-themed drone light shows illuminate the night. From there, the winter wonderland spreads across the city's most famous public spaces. Wander over to the Rose Kennedy Greenway to soar above the skyline on the breathtaking, 75-foot Frostival Ferris Wheel, offering panoramic, snow-dusted views of Boston Harbor and the historic North End.
When you are ready to warm up, head straight to Copley Square to step inside the cosy Frostival Lodge. Beautifully furnished by Wayfair, this immersive hub acts as the perfect communal living room. Gather with friends or family around crackling firepits, challenge locals to trivia nights, try your hand at curling lanes, or catch live winter sports watch parties while enjoying delicious food from Eataly.
No winter holiday is complete without exceptional culinary experiences. Frostival perfectly captures Boston's vibrant food scene, culminating in Femme Fête—a premier wine festival spotlighting talented women-owned wineries and sommeliers from around the globe. Best of all, Frostival seamlessly ties in beloved local staples like Snowport in the Seaport District, ensuring endless craft vendors and hot cocoa stops are always within reach.
