Boston is different in every season, which is a fantastic reason to come back and visit.

Heads up: the winter is very cold! But with snow on the ground and holiday festivities, it can be a winter wonderland. So, if you’re willing to bundle up, the city will have a fireplace lounge and a cup of hot chowder waiting for you.

If I had to choose one, fall is when Boston really shines! The weather stays warm through October, the tourists have left, breweries and apple orchards are in full swing and the New England foliage is spectacular.

Boston has the oldest public transportation subway in the country. The “T” is straightforward to use and especially convenient if you are traveling during rush hour or to/from a game.

My suggestion is to buy a roundtrip CharlieTicket from a subway vending machine to start. The fare cost is the same regardless of which stop you get off at. You can always add more money for additional trips.

Otherwise, this town was made for walking! The city is extremely compact and if you stay in a central location, most attractions are within a 30-minute walk. For nights out, Ubers and Lyfts are always available.


A landmark in Copley Square, the Fairmont Copley Plaza is more of an opulent hotel option. Though it may seem lavish, you’ll feel right at home after being greeted by the staff and hotel’s canine ambassador, Cori. The restaurant OAK Long Bar is also an excellent old-school setting with the best martinis in the city.

Hotel Commonwealth is located in Kenmore Square, just down the street from Fenway Park. The staff goes “above and beyond” at this hotel, and it is an especially great host location for meetings or special events.

The Liberty Hotel looks out to the Charles River in the historic Beacon Hill neighborhood. The Library’s claim to fame is that it was once a prison that housed incarcerated suffragists, WWII captives, and even Malcolm X. The unique architecture and prison cell remains add an edge to a beautifully designed hotel.

Keep an eye on their weekly events: fashion shows during the fall, holiday extravaganzas, upside-down Christmas trees in the winter, and events where you can mingle with the city’s elite.

The Envoy Hotel has a modern vibe and tends to skew younger. Located in the innovative Seaport area, there are restaurants and cafes, a movie theatre, a bowling alley, pop-up shops, and a marina to explore. Envoy’s rooftop bar overlooking the city is a definite scene.


You can usually find rooms at the Boston Park Plaza for under $150 a night. Located steps away from the Boston Public Garden, most landmarks are within walking distance. The hotel was recently restored and renovated so everything is very comfortable.

The rooms are on the smaller side, but you can always hang out in the expansive lobby space or top-of-the-line Lynx Fitness Club.


The Revolution is a new budget hotel in the trendy South End neighborhood. The rooms are small (bunk beds and communal baths are an option!) but are perfectly designed to accommodate guests. The lobby features really cool decor and street art that celebrates all of Boston’s “firsts.”