Welcome to one of my favorite city travel guides I have done: Boston, Massachusetts!
This city is filled with history, so many food/beverage options, and amazing water views. I fell in love at first sight of the city by the water.
We filled our long weekend with tours, walking around, and good eats. I felt like we needed a second visit just to see everything because there are truly so many things to do and see in Boston that we did not get to on our trip.
The activities we did and sights we saw are perfect for Spring, Summer, Fall, or Winter!
Here is the Ultimate Travel Guide to Boston!
Day 1
We obviously booked our flights through Expedia! We were traveling with friends so we opted for an Airbnb instead of a traditional hotel.
We landed earlier so our Airbnb was not ready for check in.
As soon as you land, it was easiest to take the Subway from the airport to any of the stops in downtown Boston.
We headed towards Quincy Market.
Travel Tip for Boston: Get the subway pass instead of buying a one way ticket each time.
Quincy Market had food and shopping options. Since we had not checked in, we had our luggage. This was not ideal when walking the cobblestone roads.
We then walked around toward the water front and saw the Christopher Columbus Park. The statue and greenery overlooked the water. It was a perfect, sunny, winter afternoon.
After checking into the Airbnb, it was time for some food. The travel hunger was setting it so we picked the closest Mexican restaurant that was walkable.
One thing about Boston, you can walk just about everywhere!
Fajita’s and Rita’s for lunch. Food hit the spot and had a nice margarita to go with it. Not exactly your go to type of food when in the NorthEast but we were starving.
Right next to our Airbnb was Boston Common. One of my now favorite spots we went to in Boston, it had so many amazing historical statues throughout a large park area. It is the oldest park with a walking trail, bridge over a large pond, and many benches or grass area to sit and enjoy the scenery.
The Freedom Trail Walking Tour I believe takes you through all of this but we did it ourselves.
That was enough for the day so we took a power nap and then got ready for our evening on the town.
We wanted to spoil ourselves to a dinner on the harbor and let me tell you it was an experience! We chose 75 on Liberty Wharf and sat in a bubble by the harbor. Order the wine, scallops, and filet! It was to die for! Amazing food, view, service, and overall atmosphere.
After our boujee dinner, we walked next door to a local bar and had a beer while watching the end of a Celtics game (if we had the time and money, we would have went to an actual game but still enjoyed being around the fans in the local bar!)
Day 2
Tatte for breakfast which you will notice was a repeat spot on this trip.
The best iced lattes, breakfast sandwiches, and pastries! The atmosphere is adorable too. There are locations all over Boston.
We really wanted to see the Universities while vistiting so using our subway pass, we went from downtown Boston all the way up to Cambridge.
We stopped at MIT, wandered the campus and also walked along the harbor. The campus so pretty and had amazing buildings. School was not in session so it was not super busy.
Back onto the subway, we rode all the way through Cambridge up to Harvard University. This has been on my bucket list to see, the old brick buildings and the surrounding area were so cool.
We walked to George Washington’s House which was so cute and was walkable from the University.
Taking the subway back to downtown early afternoon, we had brewery tour plans.
Samual Adam’s Brewery Tour. A very affordable activity and get a few drinks obviously. The tour guide was super fun and we truly enjoyed our walk through the brewery. This was our first brewery tour so we learned a lot.
Day 3
First stop: Tatte. More lattes and breakfast to start the day.
We grabbed an Uber and headed to Fenway Park. We had a tour scheduled in the morning.
Because we came in January, there were unfortunately no games playing. But, you have to take a tour if you have never been to Fenway.
The history and structure of the park is amazing to learn and see. This was one of my favorite parts of the trip.
Now onto one of the best stops in Boston: North End! North End is basically Boston’s version of Little Italy. The streets are lined with bars and restaurants that are all Italian styled.
We spent the afternoon grabbing wine, italian subs, and cannolis for dessert.
You definitely need to make a stop at the Holocaust Memorial that is close to North End. It was very sad yet special to walk through and read the stories that were displayed.
Walking further towards the water, we wanted to see TD Garden. Since we did not see a game while we were visiting, we wanted to at least see the place. It was in a cool location too being near the water.
We walked around ChinaTown for dinner because it was near the Airbnb. Nothing crazy to see here, we were starving so we were not picky on where to eat so we chose the closest option.
Day 4
Morning Tatte clearly was repeated because it was so good. So, morning coffee and breakfast here.
Sadly this was our last day to we did not have any planned since our flight was late morning/early afternoon.
We walked from Tatte to Beacon Hill which is on the other side of Boston Common.
Beacon Hill was so charming, the beautiful brick apartment/condo complexes and all the shops below was adorable. We loved popping into the local shops and looking around.
On our walk, there is a Cheers Bar right off Beacon Hill. We did not walk in but I believe it is just a pub bar! We walked past in since my dad loves that show, had to text him a picture!
We took our last subway ride to the airport and that concluded our Boston trip!
