Boston Commons Carousel in the Park

Bleisure-ing in Boston’s North End

/bl-ei-sure/noun – the act of adding vacation days to the front- or back- end of a business trip. Business + leisure.

I attended the ZoomInfo Summit in Boston September 2017. I had been in Boston one other time, on a 6-hour layover with my friend Kate, so I jumped at the chance to land in Boston a few days early and explore.

Boston’s Little Italy (The North End)

BenCotto, my favorite Italian restaurant in Little Italy
Pesto linguine with house red at BenCotto.

I used Airbnb, as per usual, to find a spare room in a cute little apartment in Little Italy. It had to be The North End, aka, Little Italy, after all. It is part of the heart of Boston’s historical center and it holds several of the major stops on the famous Freedom Trail. I arrived with just my backpack and found my host to pick up the keys after one easy ride on the metro.

The streets of the North End were narrow, crowded, and lined with Italian restaurants, making me nostalgic for Rome. During the day it was still quite warm out, and the trees were just beginning to turn and shed their leaves. I wasn’t sure what to expect from Little Italy, but I was pleased to hear a fair amount of discussions between shop owners and passersby in Italian. Inflections were different, but I could get the gist of their meaning.

I had a list of things I wanted to do over the next few days, but as I like to do for the vast majority of my first travel days, I mostly just wandered until I found a restaurant that looked appealing (not difficult).

With one and a half days to myself before the conference started, and I think I did a pretty decent job of seeing as much as I could at a leisurely pace. I’ll admit, I hung around Little Italy as much as I possibly could to get in some Italian listening practice.

Boston Commons Carousel in the Park

Places to Eat in Little Italy

BenCotto – 361 Hanover St, Boston, MA 02113 – I ate here three times in six days. Every single time was delicious. Their house red wine went well with my pesto linguine and the fresh breeze blowing through the open dining area.

Mike’s Pastry – 300 Hanover St, Boston, MA 02113 – Would this be a legitimate list without Mike’s Pastry? Go, eat a cannoli (or three), and thank me later. Also, make sure you have cash.

Caffe Vittoria – 290-296 Hanover St, Boston, MA 02113 – It was late-ish one night when I realized I was the closest to Italy I’d get for the next 8 months… And googled “tiramisu near me.” I was not disappointed with my dessert or the atmosphere.

I Am Books Italian American Bookstore

Things to Do in North End and Beyond

Freedom Trail – There are plenty of officially- and self- guided tours along the Freedom Trail… All you have to do is follow the red brick road around the city! The trail will take you out of Little Italy and is a great way to see more of Boston.

I Am Books – 189 North St, Boston, MA 02113 – This is a little independent bookshop dedicated to Italian and Italian American authors and works. They hold Italian classes and have a great children’s section! The inside is very cozy and friendly. I purchased a pretty Italo Calvino paperback to practice my Italian reading and spoke to the woman behind the counter about my Italian progress. She was learning too!

Boston Commons – Boston Commons is a large park that has had many uses over the years. From meeting space to military training ground, the commons has seen a lot. Now it is a peaceful break from the busy city with ponds, paths, and even a carousel.

Old State House in Boston, MA
The Old State House is where the Declaration of Independence was first read aloud.


  1. Little Italy?! This is so interesting; I had never heard about this area before! I have yet to visit the States so this is one more reason as I live Italy and I have been there over 30 times! Linguine pasta type is one of my favourites too 🙂

  2. I love the “bliesure” term! My mom has been doing this all her life (which often meant I got to go on work trips with her). I’ve never been to Boston and didn’t know they had a little Italy, but now I definitely need to go!

  3. I haven’t been to Boston in a couple years, but it’s such a fun place to visit (and so many tasty places to eat)! I walked the Freedom Trail the last time I went too!

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