Two days in Boston, Massachusetts

Here is the insider’s scoop on things to do and see in Boston.

I recently spent two days with my dear friend Olivia, a Boston local, showing me her favorite spots around the city. We had the BEST time, so here are some places to add to your travel bucket list.

The Isabella Stewart Gardner Museum

Isabella was an eccentric art collector, inspired by her travels (AKA everything I want to be). She built the museum (which she later lived in) and spent her time curating an art collection, which now includes 7,500 paintings and sculptures from around the world. The museum was featured on Netflix’s documentary This is a Robbery: The World’s Biggest Art Heist, which outlines the details of 13 stolen pieces of art worth $500 million. You can see the empty frames from where the art was stolen. The museum was one of my favorite things we did in Boston.

Time Out Market

Located within walking distance, Time Out is the perfect place to grab lunch after visiting the museum. Like always, I opted for the tacos.

Harvard University

I can now officially say I went to Harvard University, and now I have a sweatshirt to prove it. We walked Harvard Square and visited The Coop for a souvenir.

Giacomo’s and the North End

The North End was probably my favorite area in all of Boston (close to Beacon Hill). We had dinner at a well-known Italian establishment, Giacomo’s. After walking the North End, we grabbed drinks at Modern Undergound, a bar below Modern Pastry, and coffee at Caffe Vittoria, an Italian coffee shop.

Swan Boats in the Public Garden and Boston Common

You HAVE to take a walk in the Public Garden and go for a ride on the swan boats when you visit Boston. It might be cliche, but it was probably one of my favorite things we did in Boston. We also took a stroll through Boston Common, a park running adjacent to the Public Garden and the oldest city park in the United States.

Acorn Street and Beacon Hill

Acorn Street is one of the most photographed streets in Boston, known for its historic colonial vibe. We grabbed cappuccinos and lattes at Tatte Bakery before taking a walk through Beacon Hill and snagging a photo of the famous street.

Massachusetts State House and Faneuil Hall Marketplace

En route to lobster rolls, we stopped by the Massachusetts State House and Faneuil Hall Marketplace, two touristy sites to check off the list.

Boston Harbor Hotel

Is there anything more beautiful than seeing that huge American flag hanging in the 60-foot archway at the Boston Harbor Hotel?

Lobster Rolls at James Hook

This is the part of the blog post where all the Boston people hate me. I do not like lobster, and I discovered that in Boston while eating the infamous lobster roll. I can assure you (like a bad breakup) it wasn’t the lobster, it was me. So try it – it’s a must when visiting. And when you try, visit James Hook for the full experience.

Shopping on Newbury Street

If shopping is your thing, look no further than Newbury Street. So. Many. Stores.

Banyan and the Beehive in South End

Banyan and the Beehive are located right next to each other in the South End, perfect for dinner and a show. I opted for the Thai chicken cabbage wraps at Banyan and they were to die for. After dinner, we grabbed drinks at the Beehive and stayed for the blues. I’m a sucker for live music.

A Tatte Bakery Beach Picnic and Castle Island

On the last night, we grabbed dinner to-go at Tatte Bakery and headed for the beach in South Boston. We made the loop around Pleasure Bay to Castle Island, the perfect way to end our Boston excursion.