My First Time in Boston

Tommy used to live in Boston, so I’m not sure he was 100% thrilled that his organization was holding their annual conference there this year. But as a new student at Harvard Extension School, I was eager to tag along and visit a new city.

Our first order of business was heading to Cambridge. We dropped our bags at our hotel, walked through the North End to the subway, and hopped on the orange line. When we changed trains to get on the red line to Harvard, I found myself getting a little nervous. I couldn’t believe I was actually going to see the campus… and that I was actually a student!


We walked through Harvard Yard and watched all the kids moving in and getting to know their surroundings. I still think it’s pretty funny that I’m twice as old as those freshmen, but I’m probably just as excited as they were to be there.

We grabbed a delicious lunch at Felipe’s (which was crazy packed) and then headed to the Coop so I could load up on Harvard merch. (Half of my closet is now crimson.) I made sure to get Harvard shirts for both my parents, and even #ToddlerGoodwin got a “Future Harvard Freshman” t-shirt. The best purchase, by far, though, was Tommy’s “Harvard Husband” shirt. (Which he made sure to wear on my first day of class later in the week.)


After my shopping spree, we dropped everything off at the hotel and changed for our evening outing. First, we walked down the Greenway to check out the Trillium Beer Garden, which had filled up pretty quickly even though it was only about 4:30 in the afternoon. We had a few glasses of rose and watched the people go by. Then we headed to Rowes Wharf for our sunset sail on the Schooner Adirondack III. If you’re looking for an easy way to see the harbor and want to make a romantic evening out of it, this is the way to go!

Afterwards, we strolled through the North End and popped into Lucca, looking for a good meal to fill our bellies. Lucca was amazing. We got a table right at the windows that open onto the street. The neighborhood was busy with preparations for the Feast of St. Anthony and the people watching was great.

The following morning, we went for brunch at The Sinclair Kitchen. (Brunch fries with chicken gravy, jalapenos, and cheese curds! A waffle flight – three different types of waffles! And an amazing cocktail that doesn’t seem to be on their menu anymore, but I bet anything you get there will be delicious!)


Then we headed to Fanueil Hall for a Freedom Trail walking tour. Being a former elementary school teacher and a bit of a history nerd, the tour guide’s commentary made for a nice stroll down memory lane as I recalled the Revolutionary War lessons that I used to enjoy teaching my fifth graders.

Later that evening, we returned to Fanueil Hall with my friend and college roommate, Judy, who made the trip down from New Hampshire to hang out with us. We enjoyed drinks and snacks outside at The Salty Dog before taking part in Clue Live – a scavenger hunt based on the board game/movie. Nearly twenty teams of wannabe detectives ran all around Fanueil Hall looking for characters dressed up as Professor Plum, Miss Scarlett, Colonel Mustard, etc. Once you found a character, you could ask them questions or “bribe” them with play money for more information. You could also take photos of certain landmarks and present them to Detective Wadsworth; for every correct photo, you earned another clue. Just like in the game, you had to use the process of elimination to determine who killed Mr. Boddy, in what room, and with what weapon. (It was Ms. Peacock in the dining room with the knife, BTW.)

After that, we hopped in an Uber to visit Eataly. We sat at a bar and the three of us split a huge charcuterie plate and a bottle of wine before grabbing dessert. The plan was to get Judy in a car and on her bus back to New Hampshire, but she ended up missing it. She came back to our hotel, we had a rollaway bed delivered to our room, and we shared a room again – just like old times!

The next day, friends of ours from high school (also from New Hampshire) came down to meet us for lunch at Legal Sea Foods before taking their three boys to the New England Aquarium. The high school reunion continued a little bit later as I met up with yet another friend who drove down from Connecticut. We walked through the North End and caught some of the St. Anthony’s parade before heading to Fanueil Hall where she and I had a drink and some snacks at an outside table at Anthem.

That evening, Tommy had an event for work, so I made another trip to Cambridge by myself. I went back to the Coop and bought a few more things, and then I walked around Harvard Yard, soaking it all in.


I met up with Tommy and his colleagues at Mija Cantina in Fanueil Hall and enjoyed some food and sangria before we split off from the group for one last stop; Tommy wanted to show me one of the places he had lived, so we went to the Back Bay area to check things out. We decided to head to the Top of the Hub (Prudential Tower) and scored seats at the bar overlooking the city skyline while we each had a glass of wine and I eavesdropped on the bartenders’ fantasy football draft. (Those accents!)

The next day, even though Tommy’s work was just starting to ramp up for the week, I had to head home. We got a coffee and walked to Mike’s Pastry in the North End to grab some breakfast. We took our box of cookies and treats back to the hotel and ate outside on the pier. I had a gob cookie for breakfast and I brought a florentine cookie home.

And then, when Tommy returned from Boston a few days later, we both went on a diet. (Not kidding.)

I had a lot of fun in Boston, and will probably have to head back for school at some point, so I look forward to more exploring! We had a whole big list of restaurants we didn’t get to make it to!

Stay: Battery Wharf Hotel
Eat: Lucca, The Sinclair Kitchen
Do: Clue Live (summer only)

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