We spent a summer living in Boston and traveling across New England, so making recommendations for a weekend on the east coast brings us back to a lot of fun memories. We thought we’d kick off a series on our weekends in New England and how to make the most of them. First up: the city that holds a piece of both of our hearts. 

Historic Charm in a Busy City

When you first arrive, Boston can be a little overwhelming. I imagine the hustle of the trains and crowds of people downtown migrating through hundreds of tourists is similar (though likely on a smaller scale) to New York City. However, Boston doesn’t have the constant big city feeling. Wherever you are, you’re most likely standing on history. Tall buildings stand around smaller, historic places, like the Old South Meeting House where the Boston Tea party was organized or Faneuil Hall, the site of historic speeches by Samuel Adams and Fredrick Douglas.

One of my favorite places in Boston is a little neighborhood called Beacon Hill. Brick row houses with cobblestone and narrow streets take me back to the 1800’s. It’s quaint, filled now with sports bars and unique stores, boutiques and consignment shops. It’s so nice to walk into the Beacon Hill neighborhood and feel like you’re out of the city and out of this century.

I couldn’t skip a post about Boston without mentioning its beautiful preservation of nature. The Boston Harbor is a beautiful place to see the ocean and the sailboats bopping up and down in the wind (It’s also a great place to grab food to go and set up a picnic dinner, which we did frequently.). Another treasure is the Boston Common and Public Garden, which are home to beautiful beds of flowers, open greenery and the infamous swan boats.

Foodies Unite

You cannot go wrong with food in Boston, specifically Italian food. Little Italy is home to some of the best Italian food I’ve ever had. Looking for something a little less expensive? Try out Quincy Market, which has something for everyone.

Italians in Boston also love their cannolis. Mike’s Pastry is the go-to if you want to try one out. I swear every time we walked down the street, we saw someone carrying a Mike’s Pastry box.

If you’re not a big cannoli fan, check out the “World’s Best Ice Cream” shop in Somerville just outside of downtown Boston. Declared so by the New York Times, Toscanini’s Ice Cream is worth the 45-minute wait in line. Savor every scoop. (If you’re not so keen on the 45-minute wait, J.P. Licks is another one of my favorite ice cream shops).

Easy to Get Around and Out

You’ll notice I didn’t say it’s easy to get into Boston – because it’s not. Traffic and parking can ruin your weekend, so if at all possible, rely on the T, ride share services, bikes or walking to get around. Public transportation was a breeze for us to figure out; you can pretty much get anywhere you want to go within an hour.

Freedom Trail is an easy 2.5-mile walking tour through sixteen of Boston’s most historic spots – plus, it leads you through downtown, where you can easily venture off the trail for a quick detour or bite to eat. The best part? It’s totally free. You can pay for a tour guide if you want, or you can take the trail at your own pace, reading the information as you arrive at each spot. In summary: bring your tennis shoes and ditch the expensive tours.

If you eventually have a chance to rent a car, don’t be afraid to spend a day going out of the city – Cape Cod, New Hampshire and Maine are all just a few hours away. While traffic can get heavy, it’s such a treasure to be able to drive a short distance, get out of the city and experience something different while still staying in magical New England. Don’t miss out on all that it has to offer – from the rich history to the white (green) mountains to the cold Atlantic Ocean.

Until next time, Boston. Cheers.

Boston Recommendations

Don’t Miss: Walking Freedom Trail, Fenway Park, Boston Harbor, Boston Common, Beacon Hill.

If You Have Time: Walking around Harvard, Little Italy for dinner, Toscanini’s for dessert.

Skip: Cheesy history tours. Freedom Trail hits the historic points for the right price (free)!