Tales of a Digital Nomad: How We Spent Two Months Living in Boston

Our best friend is obsessed with Boston. For the past four years, he has started sentences with, “When we all live in Boston one day…” more times than I can count. After four years of Boston’s biggest hype man talking it up, living with Landing gave us the opportunity to see what Boston is really all about so we could finally tell our friend whether his dream was ever going to come true.

Here’s how my husband Ivan and I spent two months diving into the history, food, and other fun things to do in Boston! 

History in Boston

One of the most iconic things about Boston is, of course, its history—namely the fact that it has a very long one compared to most cities in the U.S. Walking the historic streets and taking in the architecture sometimes made us feel like we were in Europe!

Our favorite ways to experience the history in Boston were taking the Freedom Trail, a 2.5-mile trail of 16 nationally historic sites, and taking a Duck Boat tour (these are iconic in Boston and are a fun way to get out on the Charles River). And, since we were in Boston for the Fourth of July, we even saw the Declaration of Independence read from the same balcony where it was read in 1776 for all of Boston to hear! 

Learn more about Boston’s history in our video:

Food in Boston 

Food is one of our favorite ways to truly understand the culture and people in a city, and there is no shortage of food culture in Boston! Our favorite way to spend our lunch break was grabbing an arancini from Galleria Umberto, followed by a cannoli florentine from Mike’s Pastry. People will tell you these places aren’t worth the lines and to go to a different shop, but I truly believe those people are sabotaging you to keep the lines shorter for themselves. We did try others, and these are hands down the best! 

Boston is also known for its seafood, so you absolutely must find your favorite lobster roll while you’re in town. Ours was from Neptune’s Oyster Bar. It was so simple and classic, but absolutely perfect (and their oysters were pretty great, too!). 

I was surprised to find out that Boston has a claim on being where the roast beef sandwich was invented. Our favorite was from Cusser’s. It is so juicy and flavorful. Honestly, this sandwich alone is one of the top reasons our friend wants to move here. 

Learn about Boston’s most iconic foods in our video:

Fun things to do in and around Boston

1. Fenway Park

Boston runs on Dunkin’ and sports, so going to a Red Sox game is a pretty great way to fully embrace the Beantown lifestyle (and there is actually a Dunkin’ in the stadium!). We loved going to Bleacher Bar, built into the famous Green Monster wall in Fenway Park, before the game. And, of course, we had to eat a Fenway Frank as we enjoyed a game in this historic stadium! 

Learn how to make the most of your day in Fenway here:

2. Cape Cod

Cape Cod (“The Cape”) is such an iconic vacation spot that we felt we had to go! Our favorite things we did there were visiting lighthouses, eating the fresh fish at the Chatham Pier Fish Market, and spending time at Chatham Pier watching the fishing boats come in while seals swarm the boats waiting for their share of the spoils!

Learn more about visiting the Cape on a budget here:

3. Feast Season

There is a time in the North End known as “Feast Season” where there are festivals almost every weekend honoring different Catholic saints, and we were there for the start of the season, the St. Agrippina di Mineo Feast! It was so fun to watch the procession through the street and join in the celebrations! 

Check out all of our favorite things to do in the North End here:

We really enjoyed our time in Boston. It has a great atmosphere, beautiful parks, delicious food, and the feeling that history is all around you. While I totally understand the appeal of the city, I don’t think we share our friend’s dream of “When we all live in Boston someday” after all. We’re so glad living with Landing gave us the flexibility to figure that out without the commitment. We will love visiting our friend if he moves to Boston, but for now, we’re moving on to New York City! This will be my very first time there and I can’t wait! 

Big Apple, here we come!