5 Things To Do on Your Next Trip to Boston

With so many things to do in Boston, making a game plan when visiting can be overwhelming. If you’ve already visited before or aren’t interested in doing any of the tourist-y crap, you’ve come to the right place.

Kayaking on the Charles River with Views of Back Bay

Known as the City of Champions (sorry, I couldn’t help myself), Boston is filled with history, amazing opportunities, and the best sports teams. I’m so lucky to be able to call this amazing city my home, to be able to walk down the cobblestone streets, and to experience everything the city has to offer. If you’re new to the city and looking for some fun things to do, you won’t have to look far. From small boutiques and breaktaking architecture to amazing events and sense of community, you’ll never want to leave the city.

Heading to Boston? Here are 5 things to do on your next trip.

Stroll Through the South End

With the gorgeous brownstones, locally owned businesses around each corner, and delicious food, the South End is one of my absolute favorite neighborhoods in Boston to wonder around. And the community? Amazing. You will be greeted by the friendliest faces around each corner, be in awe of the neighborhoods beauty, and will be occupied for hours by simply stolling the streets of the South End.

My favorite South End spots: Barcelona, Olives & Grace, South End Buttery, Recycle Studio, Beehive, Niche Urban Garden Supply

Grab Margarita’s at Lolita’s

I went to Lolita’s for the first time this past spring but I am freakin hooked. With two locations (Back Bay and Fort Point), it’s always convenient to stop in to get a margarita. If you’re visiting during the warm weather, the Fort Point location has the absolute cutest patio situated along the harbor walk.

What to order: lolita margarita, hot queso dip, dry aged ny strip steak, los treos, spicy cucumber margarita, and of course, tequila shots (served with an orange instead of a lime – so good!)

Kayak on the Charles

Kayaking the Charles (or out of any of the locations around the city) is a great way to see Boston from a different vantage point. Grab a few friends, spend the morning wondering the shores of the city, snap some great pictures, and head to brunch once you’re done! Adult rentals start at $16/hour and if you’re not into kayaking, Paddle Boston also offers pedal-drive kayak, paddleboard, and canoe rentals.

Isabella Stewart Gardner Museum Garden

Visit the Isabella Stewart Gardner Museum

The museum, once known as Fenway Court, was the home of Isabella Stewart Gardner for many years and houses her personal art collection. The art collection includes European, Asian, and American art, paintings, sculptures, and more as well as some of Isabella Stewart Gardner‘s personal posessions. In 1990, thirteen pieces of art were stolen from the museum, which is still the largest unsolved art heist in history. These pieces of art are valued at over $500,000,000 today. When wondering through the museum, you’ll be able to view some of the frames that once had art in them. Very eerie.

WBUR and The Boston Globe have an amazing  podcast called Last Seen, which dives into the heist, what the FBI knows, and even interviews some of the individuals that have connections to the heist. I highly, highly recommend checking it out before heading to the museum!

Eat at Barcelona

I don’t know how I lived twenty-four years without experiencing tappas. As someone who gets full easily and opts for small meals throughout the day, it’s like tappas were made for me. With two locations (South End and Brookline) and a gorgeous (almost rustic) atmosphere, the wine bar is a no-brainer when planning a date night or brunch with the girls. Did I mention they have a bloody mary bar on the weekends?

What to order: charcuterie & cheese (duh), blistered shishitos, jamon & manchego croquetas, swordfish a la plancha, house marinated olives

What are your favorite things to do in Boston?

Leave a Reply


  1. 11.7.18
    Tori said:

    I’ve never been to Boston, but I had a friend who lived there for awhile and she LOVED it! I’m definitely going to add it to my list of places to visit. Crazy that they still haven’t solved that heist!

  2. 11.7.18
    Lexi said:

    This is awesome! Definitely bookmarking for our next trip.

  3. 11.7.18
    Brittany said:

    We went to Boston a few years ago & absolutely fell in love with the city! We didn’t do any of this, but I’m putting it on the list for next time! We ate at Antonio’s and I still claim it’s the best meal I’ve ever had!

    Brittany | http://www.pointed-north.com

  4. 11.7.18
    Jessica said:

    OMG I LOVE Lolitas! It is one of my faves. We used to live up in Boston and would go there all the time. I am also a HUGE fan of Estragon and Toro!
    xo Jessica

  5. 11.7.18
    Maria said:

    I went when I was young, so don’t remember much, so thanks for this. I would like to visit again some day before I get so old I won’t remember it either!

  6. 11.7.18
    Cathy said:

    This looks like such a fun trip! I’ll have to check these things out when I travel to Boston.


  7. 11.8.18
    Anabelle said:

    Boston is on my list of places to go! I definitely need to try all of these places. Such a good list!

  8. 11.8.18

    Amazing Boston travel guide, I live kinda of nearby so I’ll definitely have to check this out! https://mariannyc.com/2018/11/05/make-up-revolution-review/

  9. 11.8.18

    I need to add Boston to my list!


  10. 11.8.18
    Kileen said:

    These sound awesome! Definitely need to bookmark this for future reference! Makes me want to book a spontaneous trip!

    cute & little

  11. 11.8.18
    Rach said:

    Bookmarking this post! I really want to go to Boston and need all the recs I can get!


  12. 11.8.18
    Liz said:

    That museum is gorgeous!! I’d love to visit Boston!

  13. 11.8.18
    Laura said:

    That restaurant sounds soo good! These pictures are beautiful too!

  14. 11.8.18

    LOVE Boston! I actually have not done any of these things…love that they aren’t typical tourist things!

  15. 11.8.18

    I’m dying to go to Boston! Looks like you had an awesome trip!

    xo, Hillary | hillheady.com

  16. 11.8.18
    Jessica Camerata said:

    I need to go to Boston again! So much I didn’t get to see or do!

    xo Jessica
    My Style Vita

  17. 11.9.18
    Amanda said:

    I have not yet been to Boston but it’s been on my list. When I finally do go (hopefully soon!) I’ll have to check out some of these places.

  18. 11.9.18
    Katherine said:

    Perfect timing! My husband and I are planning a trip to Boston this winter. Pinning now for later!

  19. 11.10.18
    Rachel said:

    Old North Church, Skywalk Observatory, Ballet, Tea at the Boston Library, Tatte Bakery, walk down Beacon Hill! I have so many Boston faves!

  20. 11.12.18
    Greta said:

    I’ve never been to Boston but have always wanted to visit! Sounds like such a fun city!

  21. 11.14.18

    oh i love these! my husband went to school in boston so i’m sure we will be back visit sometime soon!!