Boston Itinerary

My Husband and I road tripped our way from Indiana to Boston (then on to Bar Harbor, Acadia, Quebec City, and Niagara Falls before returning to Indiana) to experience the city, but also the world cup (Scotland vs Haiti). We left Indiana and stopped halfway in Hershey Pennsylvania before going the rest of the way. Our route was perfect and leaving around 7:30am allowed us to miss a lot of work related traffic on a Friday. We passed the New York City skyline and entered Boston around 4:00pm allowing us the evening to start exploring.

Indiana to Boston Route

Full East Coast Route

Day 1

Accommodations: Due to the World Cup, accommodations were extremely expensive. We had this trip planned before it was announced as a hosting city and we kicked ourselves for not booking our accommodation before the World Cup was announced. But we found an Airbnb to stay at and made do. I will, however, not be sharing any information on the Airbnb. It was clearly someone just renting out their own place to make some extra cash. The place was disgusting and looked like it hadn’t been cleaned and to top it off the private outdoor balcony had a dead animal decaying on it. Luckily the only time we spent in our Airbnb was to sleep and shower so we were in and out very quickly. This location was just very dirty so after that experience, I will not be sharing the link.

Our general location was in South End. We really enjoyed this area as it was quiet plus close to shops and restaurants, but far enough away from the incredibly busy city center. We parked in a garage and did not move our car again and walked on foot everywhere. Parking in Boston is no joke so be prepared to go in circles or find a garage and stay there. We clocked close to 20 miles in walking just in our 48 hours in the city.

Food & Drinks: We had a dinner reservation at Saltie Girl at 7:30PM so we changed out of our roadtrip clothes and got our of our Airbnb as fast as we could. We stopped for a drink at Clerys on our way and felt the energy of the upcoming game buzzing everywhere. We continued on to Saltie Dog and came across a city square with game festivities and a massive FIFA ball. We stopped and listened to some live music while taking in the buzzing city.

We arrived at Saltie Dog and started with some fresh oysters. They were probably my favorite of the trip so I recommend going even if you just get oysters! I ordered the Lobster Roll and out of all the rolls I had on the trip, this was my least favorite. It was bland and lacked in the fresh lobster flavor. Kramer ordered a fish sandwich though that was incredible! So I do recommend this spot, but don’t waste your tastebuds on a lobster roll. 

After we finished here we headed to Fenway to see Fenway Park and watch some of the Red Sox’s game from the Bleachers Bar. The bar is in Fenway Park and has a window into the field so without a ticket you can watch the game. We aren’t baseball fans (in fact the only reason I got a Red Sox cap was for Survivor player Boston Rob) but we felt it was appropriate to stop in before the US kicked off their first match. 

To watch the US we headed across the street to the Irish pub, The Lansdowne Pub, to watch the USA match. Great vibes and great drinks! At intermission we headed to The Bepop (halfway back to our airbnb) and listened to some live music before finishing the match at Clerys.

Day 2

Excursions: Up bright and early for a long day of walking and exploring! We knew from the get go we wanted to walk at our own pace and see the city doing our own walking tour. So we started our morning walking to Boston Commons Visitor Center to pick up a Freedom Trail walking guide and start our tour there. However, before starting our tour we hopped down the alley to Brattle Book Shop – one of the oldest and largest used bookstores in America. One of our favorite movies is The Holdovers so if you’ve seen it, then you know there’s a scene actually featured at this bookstore. We looked around a bit and decided to buy, ironically, one of the biggest coffee table books there on The Beatles.

Freedom Trail: We then began our Freedom Trail tour. This Freedom Trail digital tour covers almost everything, but I highly suggest swinging in the Boston Commons Visitor Center to snag a physical book ($9). There were also tons of tours going on so if you don’t feel comfortable taking yourself on the tour there are loads of options to choose from. 

Here are the stops on the Freedom Trail:

• Boston Commons
• Robert Gould Shaw Monument
• The State House
• Park Street Church
• Granary Burying Ground
• King’s Chapel
• The Old Corner Book Store
• Old South Meeting House
• The Old State House
• Boston Massacre Site
• Faneuil Hall
• Paul Revere House
• Old North Church
• Copp’s Hill Burying Ground
• USS Constitution
• Bunker Hill Monument

The Boston Tea Party Museum Experience: We made it through to Old North Church before having to head to The Boston Tea Party Museum and Experience. This is an interactive experience with characters, videos, and a small museum section. We really enjoyed this experience and the history with it. I highly suggest booking this if you are interested in history! 

While we walked around, there were loads of different vendor shops lining the streets selling their craft. We took many breaks to look and see what they had and escape the sun. Speaking of the sun, the heat there really is no joke in the summer so I suggest keep a water with you at all time and curating your itinerary to include air condition stops. 

Originally we were going to attend the FIFA Fan Fest downtown, but we ended up opting for a local pub on Marshall Street to watch the game in and we are glad we did. Being shoulder to shoulder with Scotland fans watching the match and celebrating the goal made us feel like we were back in Scotland. And in the end Scotland won and the celebration carried out onto the streets with everyone feeling alive and cheering Scotland on! It was truly electric and something we will never forget. If you ever have the the opportunity to attend a city hosting the World Cup, I highly recommend it. 

Food and Drink: We got coffee first thing in the morning at Cafe Nero (we aren’t big breakfast people so we just needed something to get the morning going. We then stopped at Ziggy’s Coffee Bar (which loops into Beantown Pub) and got another cup of coffee with some pastries. If you stop here, you have to try the French Toast Muffin. One of my favorite pastries from the whole trip!

We had a lunch reservation at Union Oyster House and if you don’t want to wait in long lines, i highly suggest making reservations when at all possible. Obviously the World Cup was going on so it was a bit more busy than usual, but the last thing you want to do is wait when you’re hungry. We enjoyed oysters and lobster rolls. The Oysters are served by the half and full dozen and were delicious. But maybe an unpopular opinion here, I preferred Saltie Girl’s oysters and sauces. The lobster roll was fine, but truly didn’t hit it out of the park for me. We were originally just stopping for a snack of oysters and an appetizer before getting a late lunch of lobster rolls at Neptune Oysters, but time moves too quickly and we just didn’t have enough time to do it all! Next time we will stop here, but be warned it is a busy local favorite and they do not accept reservations. 

We had a dinner reservation for Aria, but after being in the heat all day we really weren’t feeling a heavy or long Italian dinner. So we cancelled our reservation and made way for some El Jefe’s Taqueria tacos at Uncommon Corner. Tacos were fine enough and it was nice to be in a breezy, shaded space with live music. 

We then went to Beantown Pub to watch the first match of the evening and escape the heat while we waited to make our way to Marshall Street for Scotland. We ended the night watching Scotland vs Haiti at Hennessy’s and it was electric! Everyone was watching, the speakers were blasting the match, and the unity of everyone cheering Scotland on was something out of a movie. 

Final Thoughts

Our time in Boston flew by, but we will be back! We loved the city and how beautiful it is. There is so much to explore and there is something there for everyone. A few places I had on our list that we passed, but didn’t have time to explore or simply didn’t get the chance to see  include:

• Public Garden
• Beacon Hill
• Fan Pier Park
• Faneuil Hall & Quincy Market
• Esplanade
• Boston Public LIbrary
• Newbury street –  home to some of Boston’s best local shops.
• Prudential Center

We can’t wait to go back to Boston one day!