Long Weekend in Boston

I’m not sure if there’s anything that I love to do more than traveling to different cities, exploring all that they have to offer for food/drinks and fun, and doing it with my SO and two of our best friends! On our recent trip to Boston, we got to do just that! Jeff had never been to Boston before, despite being a Red Sox fan, so I knew when we couldn’t go see The Carters when they came to Chicago, selling him on going to see them at Gillette on a weekend the Sox were in town wasn’t going to be too hard. Neither was talking our friend James (top left), who used to live in Boston, into coming with us! Or encouraging our friend Anooj (top right), who lives in NYC, into coming to meet us. All the pieces for a memorable trip fell right into place.

Except for our flight to get out to Boston.

We were supposed to depart from Milwaukee on a Thursday at 1:10pm. After a few delays for our flight to Baltimore and our connecting flight to Boston, eventually our first flight was cancelled. That day Baltimore was just getting pounded with storms, so our first option to be rescheduled was not until after 10:30pm that night. Which meant that we missed our first planned event for the trip – being able to see Shaq as a DJ (yes, Shaquille O’Neal). So that was a bummer, but we recovered well. Friday night was Sox game night, so we got into our gear and head out to explore a bit before the first pitch.


Inevitably, our first stop was to Cheers to grab a beer and a pic and to see if everyone knew our name. They didn’t, but we did end up meeting a lovely older couple from West Bend, not too far from the city we call home in Wisconsin. After our beer at Cheers, we found a pop-up beer garden right along the river, and enjoyed a few more cold brews before the impending afternoon storm showed up. Once safely in our Lyft and on our way to lunch, we found ourselves at Legal Sea Foods. I’m not a huge seafood fan, meaning I don’t venture too far away from the shrimp options and it’s always fully cooked, but I very much enjoyed my fried shrimp and sangria for a nice light lunch!

After lunch, we visited another pop-up beer garden in that neighborhood that featured a few delicious sour beers that I loved! Trillium Garden on the Greenway was an awesome stop for our day and the Peach Fated Farmer Wild Ale and Free Rise Saison were delicious options to keep me cool on a particularly hot summer day in Boston. After the beer garden, it was time to head in the direction of the stadium to get ready for the Red Sox game! Jeff is a big Red Sox fan, so being able to see Fenway Park, the Green Monsta, and the neighborhood around the stadium was an awesome experience for him! It helps that we got to see a pretty interesting game and, most importantly, a Red Sox win!

With all of that excitement under our belts, it’s hard to believe we had a few more days left on our trip! Saturday started out as all of my favorite Saturday’s do, with brunch. We headed over to Jamaica Plain for a bite at Canary Square! I enjoyed a typical mimosa, brunch fries, and their fruit/yogurt bowl. It was the perfect mix of salty and sweet to satisfy my brunch cravings. After brunch, we didn’t have to travel too far to get to our next destination. Being that it was International IPA Day, we thought an IPA tasting at Sam Adams was the perfect way to celebrate!

We were able to sample a few new innovations they’ve developed, being that their brewery where they hold tours is mainly where they’re trying out new styles and flavors. For International IPA Day, we sampled…

  • Samuel Adams New  England IPA
  • Samuel Adams Rose Brut IPA (my favorite)
  • Samuel Adams Mango Guava IPA

After the tasting, we took a trip to a swamp to sample a few more beers and wait for the rain to pass. At Turtle Swamp Brewing I enjoyed their FINE. beer, which was a delicious sour. They had a lot of seating which made it perfect for our group to relax, drink some beers, and enjoy some games. The perfect rainy Saturday in my book.

And that brings us to SUNDAY! Not to say it was the main reason for the trip, but it’s what I was really looking forward to the whole time. Jeff and I were the only ones planning to go to the show, so we said goodbye to our friends and made plans to get ourselves from Boston to Foxborough. It may have been easier to rent a car for this venture, being that Gillette Stadium where we were going to watch the On the Run II Tour is about 40 minutes away from Boston, but we made it work.

Thankful for the ease of trains for commuting on the East Coast, we took the commuter train towards Providence, got off in Mansfield, and took a Lyft over to the stadium. There was a special train heading from Boston to Foxborough, but I am sure it would have been pretty packed and it didn’t arrive until about 30 minutes before the show was about to start. Knowing that this was a new stadium for both Jeff and I, and there was an entertainment district near it, we wanted to arrive a little earlier so we could grab a drink and not have to rush. Thankfully we did…

As we were going through security and ready to head up to the nosebleeds, we were asked by a woman what section we were in. As I was fumbling to remember if it was 301 or 310, she simply said “these are better” and handed me two ticket stubs. She directed us to go back out of security and find the gate for Field Seating. WAIT, WHAT???? Did she know it was our anniversary? Jeff’s first time to Boston? How long it was going to take us to get home after the show? All I could think was who was this woman, how am I getting scammed, or did she really just say Field Seating when I told her we were supposed to be sitting at the highest elevation in this stadium?

But this time it was no tricks, just treats! Our tickets scanned correctly and they let us onto the field. We weren’t the only ones who got the upgrade, but damn did we feel pretty special walking on the same surface as Tom Brady does many times in the Fall, feeling like we could reach out and touch The Carters when they took the stage, and looking all the way up to our purchased seats from the ground! It was just the icing on the cake, because The Carters didn’t disappoint at all! They were amazing. Still speechless. As usual.

After the show, we opted to take a Lyft back to Boston to avoid the crowds heading back to the train. Despite sitting in the Lyft, in the parking lot, for an hour, we made it back with only a small hole burned in our wallet. At least compared to some riders who may have been taking an Uber. When I was able to get the Uber app to load, a fare estimate I received was for $130+ from Foxborough to Boston. When Jeff was able to get the Lyft app to load, and probably due to less people trying to use Lyft, we jumped at an estimate for $45. It ended up being a little bit more, but still half of what we would have paid for an Uber. Just saying. It may be our last trip to Gillette since it’s not the easiest of stadiums to get to and to leave.

Being exhausted from the previous day’s events, it was nice that our Monday consisted of sleeping in and a day spent doing whatever our hearts desired before our flight back to Milwaukee later in the evening. This allowed us to get our tourist on, get a state capitol pic for my bucket list, and enjoy some tasty eats! First stop once we slowly rolled out of bed – Mike’s Pastry! I probably shouldn’t mention that we didn’t get a cannoli, but the dessert for lunch that we had was amazing! And large. We definitely shared it once we saw the size of the delectable desserts and pastries.

After Mike’s, we enjoyed our time walking around the city! We did a bit of walking along the Freedom Trail, made a stop at Faneuil Hall Marketplace, and explored Boston Common. It was a gorgeous (but toasty) day in Boston, and we were thankful for the sunshine! One of our last stops before we needed to head to the airport was Giacomo’s Ristorante in the North End! Thanks to some key advice from a coworker, we arrived at Giacomo’s right before they opened at 5:30pm, got a table in this small, but fantastic restaurant and enjoyed a great meal! Within 5-10 minutes of our arrival, all of the tables were full and a line was starting to form outside. We opted to split a penne pasta dish with chicken, broccoli, in a vodka cream sauce. It was ahhhh-mazing! Would definitely recommend, and if the opportunity arises, I would definitely go back!

It was a crazy busy couple of days, but one amazing adventure and some great memories! Tons of delicious food and drinks tasted, great views, a Red Sox win, and just a ton of fun with a few of my favorite people!

Have you been to Boston? Any other tips and recommendations for when we go back, because I know Jeff will need another trip to Fenway!

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