massachusetts: a quick boston guide

Cup Of Jo


Today I’m curating a quick little guide to some of my personal favorites from a city that I’ve adored and loved with all my heart- Boston. Can you tell I’m feeling a little reminiscent?

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Boston is a city that I’ll always place on the highest pedestal because thats what this city deserves. From growing up visiting to packing up my life and moving there, I cherish everything about this place. All that it’s done for me and the memories captured, it’s my little niche. So today I’m very excited to share some rudimentary things to know about the city, spots to eat at, sights to see, and things to do- all the goodies. Little disclaimer, I’m writing this with the notion that you’re visiting post COVID and everything is happy-go-lucky business as usual. 


My favorite thing about Boston is that it’s the perfect walking city. If you really wanted to get some steps in you could easily walk to each area of the city and still see all the best things in one day. I highly recommend walking but if that’s not your thing the T is a great alternative solution. Find a full guide to the MBTA here.

Screen Shot 2020-06-24 at 6.39.27 PM TIP: If you’re not staying directly in the city, my recommendation would be to drive to the nearest train station and take the T into the city. Parking is a pain and expensive as heck once you’re physically in the city.

Food & Drinks

Okay my true list is on a 10 foot scroll but I’m going to find the strength to narrow this down to 5 of my favorites.

Bostonia Public House– From brunch to charcuterie boards to drinks this is a great place for good eats and nice ambiance.

Toro– Feeling some Spanish flavor? Toro has my favorite Mexican street corn and a ton of delicious tapas- you’re going to want to try them all!

Luke’s Lobster Back Bay– Want to grab a quick lobster roll but you’re not near the Boston Harbor or Seaport, do not fret. On Newbury Street you can find lobster STUFFED to the bun brim here. So delicious.

The Barking Crab– Speaking of seafood lovers, this super casual outdoor bench style seating seafood restaurant right on the water is a must go-to. Right in Seaport, get you some fresh seafood and a great view.

The North End– For my Italian cuisine lovers…I got you. Head over to the North End and have your choice at the best Italian restaurants. There’s truly so many good ones to choose from so you can’t go amiss. Not only will you leave with dinner but you’ll for sure walk away with a cannoli too (check out Mike’s Pastry or Modern Pastry)!

What To See What To Do

Beacon Hill- A stroll through cobblestone roads and beautiful picturesque Victorian brick homes and popping into cute boutique shops and restaurants, you’ll fall in love with this little area the moment you lay eyes on it. TIP: Acorn Street is a popular place to snag some selfies! And hit up Charles Street for shops and eatery.



Boston Harbor- One of my favorite spots to go on a nice summer day and conveniently next to Faneuil Hall, it’s a stellar place to wander. I love walking through the Christopher Columbus Waterfront park and continue along the water making my way towards the Boston Aquarium. TIP: I love catching a sunset here!



Boston Commons @ Park Street & Public Garden- The miniature version of Central Park, as I like to call it. Want a place to people watch, work out, hang out, then this is your spot. I love aimlessly wandering the two parks and it’s small enough to walk the entire thing which is convenient! The Common’s has Frog Pond that turns into an ice rink in the winter. And in the Public Garden be sure to walk over the foot bridge for some really great views.


Shopping- Need to get your retail therapy on? Yeah, me too! Newbury Street consists of the well known name brand stores like Cartier, Valentino, Tiffany’s. But you can also find Victoria Secret, Nike, H&M and a ton of cute boutique shops to check out. If you want more of an indoor setting than head to the Prudential. You can find stores like Kate Spade, Barnes & Nobles, Lululemon, Pandora, check out the directory here.  Downtown Crossing  has Primark, Bath and Body Works, Forever 21, and more. At Faneuil Hall you can find Abercrombie, Sephora, The Black Dog, see the whole directory here.

Fenway and/or TD Garden- Sports buff? Go see the Bruins or Celtics play at the TD Garden. Got tickets to the ball game? It’ll be off to Fenway for you.


Harvard/Cambridge- One of my favorite spots to hit up is Harvard University in Cambridge. Hit up the Red Line on the T and jump off at Harvard. I’m all about the leisure strolls and if you are too, aimlessly wandering through the University is a sweet treat. And if you find yourself out on the main streets you can find a plethora of bars and restaurants to choose from.


I could go on an on about this city but to not overload this post we’ll keep it at this. If you need more astute navigation on anything, don’t hesitate to leave a comment below or reach out to me directly. Always happy to help 🙂 Love you all.


xo, JJ

2 thoughts on “massachusetts: a quick boston guide

  1. LOVED reading this guide! Your love for this city really shined through sweets! How you feel about Boston is how I feel about New York. It changed and shaped me and I am so grateful for that!
    I know I have told you, but I only really started to explore Boston as an adult, (despite living three hour from there!) and while they it will always be my rivals in sports, it is a gorgeous city that I have come to adore. The waterfront especially is one of my favorite places. And I LOVE the Harbor Islands! They are the best! Thanks for sharing this sweets! Your pics are stunning! ❤

    Liked by 1 person

    1. I love that we both have had similar life changing experiences with our cities- being able to look back and reminisce gives me ALL the feels ❤ Oh gosh I still need to get over to the Harbor Islands I can't believe I haven't gone yet but I know that if you loved them then I will too!! ❤


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