Boston is my new favorite winter weekend
An easy getaway and a design-forward hotel that turns Boston into the perfect cold-weather escape
Ed. note: This stay was hosted by Four Seasons Boston. As always, I only share experiences that I genuinely love, and all opinions and recommendations are entirely my own. Thank you for reading and supporting my work!
There is a particular kind of wintertime trip that feels almost medicinal: low effort, high comfort, and close enough that you do not need to rearrange your entire life to take it. And each season, I find myself craving a getaway that does one thing well: make the season feel intentional. As a New Yorker, Boston was exactly that for me. I boarded the new Acela train on a gray December morning, stepping off a few hours later into a city that felt instantly—unexpectedly!—charming. And at the center of it all was Four Seasons Boston, a hotel that understands winter not as an inconvenience, but as a season to lean into with hospitality so warm you forget how frigid it is outside.
Exploring Boston
Some places do not require you to “find the magic” in the wintertime. It is simply there the moment you arrive. Boston was like that for me: twinkling lights, cobblestone streets made for wandering, weeping willows leaning over frozen ponds, bookstores that feel like film sets, and a rhythm that makes the cold feel charming instead of punishing.
This was my first time visiting, and I was instantly taken with how walkable and warm-spirited the city feels, especially in December. My home base, Four Seasons Boston, could not have been more perfectly placed. Set directly across from the Public Garden, it sits at the gateway to everything. A short stroll through the park leads you straight into Beacon Hill and its rows of brownstones, tiny shops, and idealistic streets that feel almost too pretty to be real.
I wandered into the Beacon Hill Bookstore to warm up and read a few pages of Eliza Clark’s new novel before continuing on. Lunch was a chicken pita at Tatte Bakery that was so good I returned the next day to have it again. Ice skating (for the first time ever!) at Frog Pond rounded out the afternoon: a little slice of old-school Americana framed by families fully committed to having a Hallmark-movie afternoon. I genuinely would not be surprised if I showed up as a background extra in some Christmas-themed rom-com next year.
Standout amenities you won’t find elsewhere
What sets Four Seasons Boston apart is not just the location or the service, but the amenities that feel genuinely one-of-a-kind in the hotel world. It is the first Four Seasons to debut its own in-house coffee shop, offering complimentary lattes and cappuccinos to guests each morning. As someone who considers leaving the hotel for coffee an act of violence, being able to start the day with a good coffee in hand—not lobby coffee, not powdered cappuccino, but an actual barista-made drink—felt like an indulgence disguised as convenience.
And then there is The Vault. Every floor has one: a complimentary snack closet stocked with chips, candy, popcorn, sodas—mini bars could never! It’s the kind of amenity that sounds simple until you experience it. No overpriced mini bar or rationing the one sad protein bar you brought from home. Here, you get a steady supply of salty and savory snacks available whenever you want them (which is constantly, if you’re me). I’ve stayed in a lot of hotels; this is a feature I wish every property would copy.
Little guests of honor
Another standout quality here is that children are treated as true guests of honor. During check-in (typically the most boring part of the hotel experience for kids), staff present them with a special golden key that unlocks a secret toy closet behind the front desk. They’re allowed to wander inside and pick out a couple of treasures to take home: everything from little wind-up animals to Slinkys to Four Seasons–branded rubber ducks. I love the intention behind this experience, and the magic the hotel is so intentional about creating for its littlest guests. Starting ‘em young as loyalists—love to see it!
Your winter weekend, perfected
What makes Four Seasons Boston special in winter is how deeply it commits to the season. It is not relying on the usual cold-weather shorthand: a lone fireplace, a cup of hot cocoa. Everything here is considered and actually fun, transforming the cold into something to savor rather than survive.
The spa is the hotel’s warmest embrace: a steam room, sauna, hot tub, and pool arranged like a miniature wellness village. After wandering snowy streets or skating in the Common, stepping into that heat is true luxury. It is the kind of amenity that changes the pace of a trip: you warm up, slow down, and all of a sudden, winter feels indulgent instead of exhausting.
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Instead of handing you a drink by the fire, Four Seasons Boston outfits you for an actual adventure. A picnic basket is delivered to your room filled with hot cider in a thermos, beanies, cookies, and hand warmers—a thoughtful kit for ice skating at Frog Pond just across the street. Afterward, you can thaw out at Coterie, the on-site restaurant, with their Apres Skate menu: beef bourguignon, poutine, and hot chocolate (boozy if you so choose).
What to pack
For packing, I kept things simple and warm: HeatTech base layers (don’t skip these!!), a cashmere sweater for layering and dinners, and a puffer jacket that handled the wind. Cashmere-lined leather gloves were the only thing that kept my hands warm while skating and walking through the Common, so I’d highly recommend a pair of these as well. Bring your walking shoes, too!
The bottom line
If you are craving an easy winter getaway from NYC, Boston checks every box: seamless travel, charming streets, warming food, and a hotel that leans into the season with real personality. Four Seasons Boston feels intentionally cozy and seasonal without ever sacrificing polish. And in a season that can feel overwhelming in every direction, there is so much luxury in a getaway that handles the heavy lifting for you. Just get on the train and let the weekend unfold.
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Tori Simokov is a Travel Writer and Graphic Designer/Strategist based in New York. To get in touch, email tori@v1projects.com. Want more? Check out Instagram, TikTok, or shop her curated favorites.
Thank you for taking me to Boston!
I was thinking Manitoulin Island, Des Moines, or Boise. Low key, hopefully low class, and probably people that do not give a damn about who you are or think you are. My kind of crowd!