A Boston Winter Weekend

Boston with its cobblestone streets steeped in American history, its compactness and its small-town feel is the heartbeat of New England. It’s a city to fall in love with on sight and to fall in love with over and over again as it slowly reveals its secrets. It’s almost perfect to visit anytime of year, all right, I’ve heard you shouldn’t go to Boston in February and after the winter the city is having that’s probably good advice. But even if you find yourself in Boston while it’s snowing there’s still plenty to enjoy in the iconic American city.

One of the many benefits to a wintertime visit to Beantown is having your choice of hotels at their cheapest. The city’s compactness makes finding a centrally located hotel easy; all you need to know is which neighborhood you want to spend your nights in.

In the South End, Boston’s up and coming neighborhood, stay at the Seaport Boston Hotel and World Trade Center. Located near Logan International Airport the hotel is just as popular with families as it is with business travelers and if you drive up in your Tesla or hybrid, valet parking is free for a night. Across the street is the convention center where something is always happening, just over a mile away is Faneuil Hall, which even in the winter is not a bad walk and in between are the galleries and restaurants that are sprouting up in the South End.

For a weekend emerged in Boston’s architecture stay at Loews Hotel Boston near Copley Square. The limestone building that once housed the Boston Police Headquarters has the Back Bay neighborhood as its backdrop and is just a short hop to the shopping on Newbury Street and historic sites such as the Old South and Trinity Churches.

For the troublemakers that my feel out of place in the rule abiding former police building a stay at the Liberty Hotel in Beacon Hill is for you. Panoramic views of the city, close to public transportation and you can soak up history from inside the hotel. In another life it was former jail, ask for one of the rooms that used to be a cell.

Wherever you stay pick a hotel close to the T and you’ll be happy.


If you’ve been to Boston as a child it was probably during a field trip to one of the city’s many historic sites. Visit a few again, you’ll enjoy and appreciate them more. Start at Faneuil Hall Marketplace. It makes a good base to plan out what to see on the 2.5-mile freedom trail that hosts 16 historic sites. Unless you’re really into history, in which case you can take tour from a National Park Service Ranger, pick two to three places to visit such as the Paul Revere House, the Old North Church, or Granary Burying Ground on Tremont Street to name a few.

Those staying in the South End should start with the morning with a walk around the once considered dangerous neighborhood that has become an enclave for artists and foodies. Stop at Flour Bakery for breakfast, then enjoy the art at Fort Point Arts Community and/or the Institute of Contemporary Art and if you’re looking for history and it’s not too cold pay a visit to the Boston Tea Party Ships and Museum.

The city’s other currently and always-hot neighborhood that’s worth at least an afternoon is Back Bay. Stroll the shops on Newbury Street and use ducking in them to warm up from the cold. Then discover the antique finds along Charles Street in Beacon Hill.

Image: Flickr Creative Commons/Igor Motov

Boston is a food paradise for both seafood and Italian lovers. For more history and delicious seafood, including an ice, cold and fresh raw bar, the Union Oyster House near Faneuil Hall is both the oldest restaurant in Boston and the oldest restaurant in continuous service in the US. Those more in the quick meal lunch mindset can have their pick of the places at Quincy Market. The cross between a mall food court and Singapore Hawker Center boasts 36 food vendors. Those seeking Italian can’t miss Mamma Maria in the North End. Rustic Italian food using local ingredients is served in a restored townhouse.

Insider Tip
Let a true Bostonian plan your trip, perhaps even a famous one. Boston.com’s Walk This Way features Bostonians sharing their favorite hometown spots.