Boston or Bah-sten, however you want to say it, was a dream!
Last week my husband and I had the chance to visit the amazing city of Boston, Massachusetts, and we had an absolute BLAST. From the food to the people and sites, everything was perfect for our quick weekend getaway. And I do mean quick; we were there for just 72-hours. But, nonetheless, we had the best time visiting friends and celebrating my birthday.
I’m excited to tell you all about our time there and hopefully inspire you to add Boston to your list of places to visit.
Here’s everything we did along with pointers for putting together your own itinerary.
Day 1 in Boston
We took an afternoon flight from Chicago and arrived in Boston Friday evening. The flight was only an hour and 45 minutes, which I was thankful for because the last place we went was London, and that was an 8 hour flight (soooo long).
As soon as we landed we found out the Boston Celtics were playing that night, so what did we do? We bought tickets as soon as we picked up our luggage from baggage claim! We HAD to see them play!
Actually, fun fact about Peter and I. We try to go to an NBA game in every city we visit. So far I’ve seen the Lakers, Celtics, Hawks, Nuggets, and Jazz. Our next goal is to see the Knicks play in New York. Hopefully that happens in 2024.
The game was great and of course the Celtics won. They played the Knicks, so the energy within the stadium was insane. Everyone knows Boston vs. New York is a classic match up. We saw Jaylen Brown get ejected, for no reason in my opinion, made it on the jumbo-tron, and witnessed a screaming match between a couple Yankees and Redsocks fans. I’d say that was a successful first day!
Itinerary tip #1
Plan to attend a live sporting event. Boston is home to a variety of sports teams and the people of Boston are passionate about their teams. Especially the Boston Red Sox! Once you decide when you’re going to visit take a look at what games will take place during that time.
Day 2 in Boston
We started our day with a relaxing morning in our AirBnB and ordered breakfast from a local spot on DoorDash.
At 1 P.M. we headed to Fenway Park for a tour that Peter booked for us. You guys. It turned out to be one of the best tours we’ve ever done. Not kidding! Fenway Park has so much history behind it that I wasn’t aware of and our tour guide delivered the information in a fun and engaging way. I felt like a true Bostonian once we were done. Thanks, Xavie-ah! (His name was Xavier, but he said there’s no R’s in Boston LOL).
After our tour we got lunch at Lobstah On A Roll in the Back Bay area. Now THIS lobster roll was the food highlight of the weekend for me! Peter can’t eat seafood because he’s allergic, so I enjoyed it for the both of us. My main goal for the weekend was to get a lobster roll and I’m so glad I was able to. I ordered mine warm and it came with a side of butter on freshly baked bread. It was worth every cent of the $24 that was spent!
That evening we met up with our friends and within a couple hours we’d seen the whole city. Thankfully, Boston is very walkable! It was nice seeing all of the Christmas decor, especially on the North End. We also stopped in to Umbria Steakhouse for dinner that night. I had to have more lobster, of course, so I ordered Lobster Ravioli with Caviar.
Itinerary tip #2
Book one historical tour and one walking or bus tour. Boston is one of the 13 colonies, so of course it’s rich with history. There are a ton of historic tours to choose from. We chose to tour Fenway Park, but there are plenty of others out there! For example, you could tour the Freedom Trail or visit the Boston Tea Party Museum.
I also recommend booking a walking or bus tour via Viator to explore the city in its entirety. Lucky for us, we had our friends to show us around, but a walking/bus tour would be a great way to see the city in a short amount of time.
Day 3 in Boston
Our last day in Boston was the best because we actually celebrated a national holiday! MY BIRTHDAYYY!
The night before my husband set out my gifts in the living room of our AirBnb, so when I woke up I saw my card and everything. (SO CUTE!!!)
To kick off my birthday celebration we started the day with Brunch at Buttermilk & Bourbon. We had a great time of course and I felt so special and loved. Random observation, but our last day there is when I realized that a lot of the restaurants in Boston are underground for some reason. I’m not complaining, just not sure why that is.
The rest of the day was spent 54 floors up in the air in the Prudential Building with 360 views of the city. We honestly felt so boujee and I loved it. We spent the day at their rooftop bar, watching football and having good conversation. It was the perfect way to bring in year 27, especially since I LOVE watching football. We had a blast!
Itinerary tip #3
I recommend taking it fairly easy your last day in Boston. Leave room for your schedule to change. There’s so much to do in and outside of the city, so leave room to explore and go where the wind takes you. Trust me, you won’t regret it! For example, we didn’t have the Prudential building planned, but I’m glad we did it. We ended up having a great time and made some cool memories!
A weekend well spent
All in all, Boston was a great time. It’s the perfect weekend trip destination, especially if you’re looking for good food, walkable attractions, and beautiful views. We’ll be back in October and we can’t wait!
I hope you feel inspired to plan your next weekend getaway to this amazing city. Let me know if you have any questions!
