How to Spend 4 Days in Boston

Last summer my best friend and I took a much needed girls trip to a place that was new for both of us: Boston, Massachusetts. We originally picked the destination based on concert tickets (because let's be honest, you take what you can get these days…thanks Ticketmaster) but by the end of the week we both wanted to stay forever. 

In the four days we were there (it was supposed to be five…thanks Microsoft for that one) we covered a lot of ground! Check out the details below:

DAY 1: Back Bay

After landing at Boston Logan International we headed to our accommodation at Copley House, a collection of guest houses in historic Back Bay. We settled into our room, freshened up from the flight and headed out to explore. When picking our hotel we prioritized location, putting us within walking distance to tourist hot spots. 

Our first stop was the Boston Public Library for happy hour cocktails in their Map Room Lounge. From there we walked around the block to see Trinity Church, Old South Church and Boston Commons. On our way back to the hotel we found a sushi spot with an empty table, a nearly impossible feat at any other restaurant nearby (make those reservations people). With full bellies and happy hearts we turned in early to rest up for a packed day two. 

Tip: Before our trip we purchased the Boston CityPASS, giving us access to all of our activities. This was a great investment saving us both time and money. 

DAY 2: Fenway

Our second day started with breakfast nearby to fuel our trek to the Fenway area. As a big baseball fan touring the iconic stadium was high on my to-do list. Bonus points for the ability to scope out our seats for the concert later that night. The tour was fantastic with knowledgeable tour guides and a fun group of fellow tourists. We stopped by the team store for souvenirs and walked to our next destination. 

The Isabella Stewart Gardner Museum was my favorite activity of the trip. Before we went I had little knowledge of Isabella or her extensive collection of art and historical artifacts. We saw everything from personal correspondence with authors and artists, to the infamous empty frames of the museum's 1990 art heist. If you are planning to add this to your itinerary, which I recommend you do, make sure to set aside plenty of time to go through each exhibit (and don’t forget the audio tour). 

Determined to see every piece of art in the Boston area we took a short stroll to the Museum of Fine Arts. Double the size of Isabella’s we left much of the museum unseen due to time. The extensive collection covers works from ancient empires, the Italian Renaissance, the age of Impressionism, and so much more! I even saw my first Monet! 

We rounded out the day at Saltie Girl (where I tried oysters for the first time!) before catching the subway back to Fenway our main event: the Noah Kahan concert! It was hands down the best concert I have ever been to. Plus, finishing with Sweet Caroline in Fenway? Iconic. 

DAY 3: North End and Beacon Hill

Our third day was full of historic landmarks. We started with the Boston Tea Party Ships and Museum where we participated in the dramatized reenactment of the events. We even got to toss some tea into the harbor ourselves! I was surprised to learn during the tour that the last crate of English tea from the tea party was last seen in Knoxville, TN where I was living! 

From the ships we walked towards the Boston Harbor checking off Paul Revere’s House and Quincy Market. Once at the harbor we booked a city cruise using our CityPASS to give our feet a break while still enjoying the city! After the cruise we headed to Little Italy for dinner, squeezing into the highly recommended Giacomo’s. It was worth the hype and I still have dreams about their mussels and pasta. Fueled up from all the carbs, we made our way back to Boston Commons to meet up with the Haunted Boston History & Mystery Walking Tour which, you guessed it, was also included in our CityPASS. While I enjoyed learning more about the city, this activity would be one I consider optional. It was more historic and less haunted than I was expecting. If ghost tours are something you really interest you I would recommend checking out other companies for this one. 

Since we were already out late we grabbed a beer at Sam Adams brewhouse near Quincy Market and watched the Red Sox play (I mean come on, if you're in town during the season you have to watch them somehow!).  

Tip: If you have dinner at Giacomo’s, and I recommend you do, make sure to have cash! If you forget, there is an ATM on site. 

DAY 4: Downtown and Seaport

We started our last full day with breakfast at the Friendly Toast - an eclectic all day brunch spot popular throughout New England for their eggs Benedict and mimosas! Then we headed off to the JFK Presidential Library. Both of us are government and history nerds so it was a must for us. It took us a lengthy subway ride and a long walk but it was so worth it.

I have a special fascination with the Kennedy’s so it was exciting to see everything from the First Lady’s dresses to a replica of Robert Kennedy’s attorney general office. 

We spent most of our day taking our time through the library but with plenty of daylight left we decided to check off the USS Constitution - or “Old Ironside” - the world’s oldest commissioned warship! My brother requested photos from the so of course I had to comply as we explored the ship.

After the museum we took a break from touring to do a little shopping and resting. The one part of town we hadn’t seen yet was Chinatown so we landed there for dinner where I got to live out my childhood dream of having hot tea with my meal.

DAY 5: Drive home

The next morning we woke up to every traveler’s worst nightmare: a cancelled flight. But not only was our flight cancelled, so were all the others. After a minor mental breakdown our knight in shining armor (my friend’s fiancé) found us one of the last rental cars in the city. We quickly packed our things, found some coffee at Blank Street (so good by the way), and headed to the airport to wait to claim our chariot. 

Once we were on the road we decided to make our 20 hour trip as enjoyable as possible. A few hours in we made our dinner stop in a small town in Connecticut for lobster rolls and coastal vibes. I wish we could have stayed longer because it was quite the charming town! The romanticism of our road trip didn’t last long into the night, however, because we were determined to get home. About 24 hours later we finally arrived in Nashville, Tennessee, tired but happy we did it. 

If you are planning a trip to Boston soon, and I recommend you do, check out my Google Map in the “Maps” tab above! Happy planning!