I only spent two nights in Boston, and one of the nights included seeing a hockey game, so I’m sure there is lots more you could explore! But, I would also say that Downtown Boston is totally “do-able” in a long weekend. I really enjoyed the city and everything it had to offer – I loved being able to walk around and see so much, and I had nothing but amazing food the entire time I was there! So, here it goes!


  • Freedom Walk – walk the red brick starting at Boston Common (2.5 miles one way); it will help you explore all of Downtown Boston! One of my favourite things by far (granted, I like walking)
  • Boston Common – if you do the Freedom Walk, you’ll make your way to the Common, so you can spend some time there. There are often things going on, performances, skating, that you might want to check out, day or night
  • Harvard – Harvard Square is classic. Run or walk Charles River by there
  • Boston Harbor – once again, if you do the Freedom Walk, you’ll pass the harbor. If not, you may want to enjoy a meal out by the water
  • Markets – lots of cute markets to check out, mostly with food (so, winning…). All the markets are set up super cute around Christmas time. They include: Quincy Market, Boston Public Market, and Faneuil Hall Marketplace
  • Fenway Park Tour – buy tickets ahead of time!
  • Hockey Game – if you can, see your favourite team take on the Boston Bruins!

Other activities that I didn’t get a chance to do, but were recommended and/or researched:

Now to the Food…


  • The Friendly Toast (fun, diner-style spot for breakfast, with vegan options)
  • No. 9 Park (the chef’s six course tasting is so lovely for a dinner date!)
  • Spyce (salad/bowl spot, with the majority done by machines/robots. Quick lunch & unique experience)
  • Tatte Bakery & Cafe – café and quick lunch by Harvard Square (warning: will likely be crowded with students)
  • Cheers – go for a beer, if you’ve seen the show (try to go to the original one on Beacon Hill for the full experience)

Other Restaurants that I didn’t get a chance to try, but were recommended and/or researched:

Enjoy Boston and all it has to offer!!