city guides: boston

city guides: boston - taking you on a virtual tour of all my favorite stops in boston! // cait's plate

When I travel I absolutely love to explore the area as the locals would.  I think there’s something so special about seeing a city the way those do that live and work in it every day.  Before I travel, I tend to do pretty extensive research looking at blogs and different travel sites to figure out what those spots might be.

I love visiting and exploring cities and getting to share my experience with other people in the hopes that it enhances their trip there a little bit!  I’ve done posts on Greenville, Charleston, Ocean Isle BeachThe BahamasSan Francisco and Vermont like this but decided it might be fun to make these City Guides (if you define the term “city” loosely!) a part of the blog showing you what I had fun doing, where I ate and slept for different cities!

Someone recently requested on Instagram that I put together a bit of a Boston City Guide.  And while a full-blown Boston City Guide would be about 15 pages long and take me years, I wanted to make sure I put together at least something for them!  I’ll be sure to add to it as I uncover new places!

Where to Eat:


city guides: boston - taking you on a virtual tour of all my favorite stops in boston! // cait's plate

  1. Tatte Bakery – Great for breakfast or lunch!  Amazing food and coffee.  Check out the newest Beacon Hill location – it’s beautiful!  For a little more space, try their Third Street location in Cambridge.
  2. Gracenote Coffee – I actually haven’t been to this one yet but I’ve heard wonderful things and it’s on my list!
  3. Render Coffee – They have amazing coffee and delicious breakfast sandwiches
  4. Thinking Cup – They have several locations, but my favorite is the Boston Common location – it makes for the perfect warm up after exploring The Commons and The Public Gardens!  They have delicious food for breakfast, brunch or lunch!
  5. Caffe Nero – Delicious food, amazing pastries and great coffee
  6. Pavement Coffeehouse – Tons of locations around Boston.  Go for their bagel breakfast sandwiches and lattes.
  7. Appleton Cafe – Friendly service, good coffee and delicious lunch food!  I recommend their m&m cookie – one of the best I’ve had by far.
  8. Cafe Madeleine – Another one I haven’t been to, but it’s on my list!  Rave reviews from all my most trusted coffee-loving friends 🙂
  9. Neighborhood Cafe – Delicious crepes and coffee!  Also has some great lunch options.
  10. South End Buttery – One of my absolute favorites.  Their food is to die for and they have amazing pastries and coffee.

I could go on and on here but I’ll cap it at 10!


  1. Cantina Italianadelicious Italian food in the North End
  2. The Painted Burro – Awesome chips and guac, margaritas and tacos!
  3. Union Oyster House – You can’t beat their cornbread!  Plus it’s a National Historic Landmark so it’s worth going to alone to see the inside 🙂
  4. Eastern Standard – Delicious food no matter what meal you go for – breakfast/brunch through dinner are all highly recommended!
  5. Barcelona – My sister and I fell in love with Barcelona for the first time in Atlanta and were so excited to see they opened one in Boston when we moved here!  Great wines, amazing food (tapas style) and friendly service!
  6. Dorado Taco – Pretty low-key place; less of a restaurant feel but absolutely amazing food!  Highly recommend the Dorado taco, the chips and guac and their house-made sangria.
  7. Picco – Specializing and pizza and ice cream, this has been one of my favorite places for YEARS!
  8. Lolita – A little hole-in-the-wall place serving delicious Mexican food with a really cool atmosphere.  They also serve cotton candy with pop rocks at the end of the meal!

I would also recommend this article – a lot of favorites are listed and they’re much more eloquent in their descriptions 🙂

What to Do:

city guides: boston - taking you on a virtual tour of all my favorite stops in boston! // cait's plate

One of the best things about Boston is that there is so much that you can do for free.  Truly just walking around and exploring the city is amazing in and of itself because there is just so much history to it.

  1. Faneuil Hall & Quincy Market – Cutest little shops and eateries with the absolute best holiday decorations (complete with horse-drawn carriage rides!)
  2. Beacon Hill – This is one of my favorite neighborhoods to explore in Boston.  Form their hidden little alleys and streets (including the infamous Acorn Street!) to their beautiful doors and holiday decor, it’s definitely worth spending some time here.
  3. Boston Public Library – It’s worth checking out for the architecture alone.  They also have a great kids area!
  4. The Boston Common The Public Gardens – These basically run into each other (close to Newbury Street and Beacon Hill!) but are definitely worth checking out.  This is where you can take the infamous Boston Duck Tour!
  5. The North End – A cool little neighborhood with a lot of history – definitely worth taking a walk around (if only for a stop at Mike’s Pastries!)
  6. Newbury Street – Regardless of whether you love shopping or loathe it, Newbury Street has a little bit of everything for everyone!  From food to bakeries and cafes to TONS of shopping, it’s a great place to explore while in the city.

No matter what you choose to do, this city has something for absolutely everything and visiting in the winter is magical.  Feel free to leave your recommendations in the comments!



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