Hey! This post is about my amazing trip to Boston in June 2016. I’m totally obsessed with the city now and I absolutely can’t wait to get back!

My best friend, Anna-leigh, lived there for a year while teaching at Merrimack College. When I saw her at Christmas 2015, she had been living up there for about 6 months. She was talking about how much she loved it. I just couldn’t understand. All I could think was, it’s the north, it’s cold, it’s got to be bad. When I went up to visit last June, I completely changed my tune! (nice rhyme, huh?)

I’ll be honest, I knew exactly zero about Boston before going, and I expected it to be like any other city. I’ve been to Atlanta, St. Louis, and Chicago, and I fully expected Boston to be exactly like these cities. Boy, was I wrong! All I can keep saying about Boston was that it was clean! Haha, I have no idea why that’s what stuck with me, but I was so impressed with how clean it was! I also learned that Boston is, in fact, more north than New York City! I had no idea! I guess I didn’t pay much attention to geography for the north east!

My trip up to Boston was a little rocky. I scored a killer deal on a direct flight from Nashville to Boston for $200 round trip! I was super excited about this! I got on my plane, we taxied away from the gate, and then the pilot came over the speaker and said we’d be going back to the gate because there was a potential problem. After sitting at the gate for 30 minutes, we’re told to de-board the plane. After sitting in the waiting area for another hour, we’re told the flight has been cancelled! I was freaking out because this was my first time flying by myself!

Never fear! I eventually got on a different airline’s flight up to Boston and made it there that evening! I was so excited when I landed and Anna-leigh and her husband were waiting for me! Her husband had made a dinner reservation for us at one of the Italian restaurants in the North End. Who knew that Boston had their own Little Italy? I didn’t! It’s called the North End! Dinner was SO good!

After dinner, we walked over to a place called Mike’s Pastry that served cannoli’s. Anna-leigh and her husband were trying tell me that it would be packed with people and you just kind of have to make your way to the front and tell them your order. No lines, no organization, just chaos. It truly was just like that, and I loved it! Note: if you’re going up to Boston plan to go to Mike’s Pastry they’re cash only!!

The next morning, we decided to do a downtown Boston day! We parked in the parking garage underneath the Common. Which was basically the coolest thing ever! Picture walking up the stairs and coming out in this huge park!! I loved that area! We walked around the Common and the Boston Public Garden. We rode the Swan Boats around the garden. That was such a neat experience and so much fun!

From there we walked through downtown by the brownstones and to Commonwealth Avenue for a nice walk. I saw this girl walking a bunch of dogs, she must have been a dog walker, but the coolest thing was that she had like 3 goldendoodles with her!! I was freaking out about that! Then we shot over a couple streets where they had these cool shops and restaurants in the old brownstone buildings. We had lunch at this awesome burger place called Shake Shack where I got some Boston dog treats for Kingsley!

Next we walked around downtown for a bit and looked at some of the cool architecture. Boston was cool because there would be this super old building and right next to it a skyscraper!

I’m a big baseball fan, so of course I couldn’t miss a trip to Fenway Park! We walked over to Fenway, which was a good little walk, but we had a nice time chatting and catching up! Since the Red Sox were out of town, we got the full tour! We went on the field, in the stands, in the visitors’ clubhouse, in the press box, and on top of the Big Green Monster! I had a great time, even though it was the Red Sox home!!

Then we walked back to the Common and started the Freedom Trail. The Freedom Trail is a red brick line built into the sidewalks and streets around Boston that leads to all of the historic sites. It’s completely free, but you can hire a tour guide if you want. Anna-leigh and her husband had played host to so many guests during their time in Boston that they already knew all of the tour guides information and fun jokes! In a cemetery, I saw Sam Adams grave. Across the street there is a bar, which is the only place in the world that you can drink a cold Sam Adams while looking at a cold Sam Adams! Haha, thank you Anna-leigh!

Along the Freedom Trail I saw Park Street Church, the location of the Boston Massacre, and Paul Revere’s house. Then we participated in Anna-leigh’s death march (aka walking faster than humanly possible) to Old North Church. It was about to close for the day, so we had to be sure to get there!

After that we decided to take the long walk across the bridge and over to Bunker Hill. This was a really nice walk through a super cute neighborhood! Bunker Hill was also really cool! We had great views of the city too! We took a break here to rest our feet before our walk back.

We decided to have dinner at the Union Oyster House, which is the oldest continuously operating restaurant in America. There was a wait, but it was definitely worth it! I had scallops and they were delicious! Of course, the night wasn’t complete without another trip to Mike’s Pastry!

My last day there I flew out in the afternoon, so we decided to head back into the city for a morning and lunch in Boston. Which of course, I was all for!! We parked again in the super awesome parking garage under the Common, that I was just as impressed with the second time! We decided to start walking along the Freedom Trail again to see some of the smaller sites that we missed the first time during “Anna-leigh’s death march”.

We knew that the USS Constitution was one of the sites along the trail, so we thought we’d try to go see that. We ended up near the water, and found a way to get onto a dock and see the water, but we couldn’t see the USS Constitution. From there, we got lost…

Earlier in my trip, Anna-leigh had been telling us that she read this article online that listed the best pizza in every state, and that the best pizza in MA was in Boston. She said that the restaurant opened at a certain time every day and only stayed open until they ran out of pizza! She wasn’t sure where it was though. Lucky us, while we were lost, we stumbled upon it!

This place was run by Italians that hardly spoke English. It was cash only, and pizza was $1 a slice! They also had these other Italian dishes that we couldn’t pronounce and didn’t really know what they were. I tried one that was some dough with ground beef, pizza sauce, and peas inside with cheese on top. It was really good! Anna-leigh tried another that was a rice ball with the same ground beef mixture inside. She said hers was good too! We are also fairly certain that we ate lunch next to the mob, haha!

After our lunch, we were heading back to the Common and we found a Holocaust Memorial. At first we didn’t know that’s what it was. It was these really tall, clear glass statues. People were around looking at it. They were also along a sidewalk. We thought we’d check it out, and it ended up being a memorial. It had quotes from survivors and military men. It was really cool! I’m glad that we stumbled upon that.

Sadly, it was then time for Anna-leigh and her husband to take me to the airport so I could go home. I had an amazing time!! I think my favorite part of the trip was our days in Boston! I just really love the city, and I can’t wait to go back!! Be sure to look out for my post about the rest of my trip where we explored small New England coastal towns and touring the mansions in New Port, RI!

Have you been to Boston? If so, what was your favorite thing? Do you have a city that you’re obsessed with too? What’s your favorite place?


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