The Best Weekend Travel Guide to Boston, Massachusetts

In between Christmas and New Year’s, I spent a weekend in Boston, Massachusetts.

Wanting to tick off another state before the end of 2019 and of course, see another city that I’ve always wanted to see, I chose to hop on a four hour bus to the very Irish-American city of Boston, MA.

Home of the Red Sox and Boston Celtics, I’ve always wanted to visit as a lot of my family have been before with one family member having lived there for over ten years.

With a free weekend and no plans between Christmas and the New Year, I thought it a good time to explore another part of the US and to see a new city and what it had to offer.

Since Boston was only a bus journey away, and a few of the other interns had already been, that’s where we chose to go.

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You can view my most recent trip to Boston on YouTube below:

Table of Contents

How we got there & where we stayed

I took a half-day from work on the Friday and rode the 2.30pm Greyhound bus from Port Authority to Boston. The bus journey was long and cramped and took us over five hours with traffic. It was late when we arrived so walked from the bus station to our hotel in darkness, but one thing about Boston is that all of the street lights are in lanterns which made it very cute.

We stayed in the Revere Hotel in the Theater District of Boston, in the Downtown area of the city. To me, Boston was a little confusing with all of its different areas but our hotel was a ten minute walk from the bus station and a fifteen minute walk from Boston Commonwealth.

The hotel itself was very modern, trendy and our room had a huge bed that would have fit six people in and an amazing view as we were on the 21st floor.

I had a cocktail in the hotel lobby bar before making our way out for dinner on the first night which was just what I needed. That’s a strange thing about New York – they aren’t big on cocktails. What I would give to have a Pornstar Martini back in my life.

Where we ate

On the Friday night we headed to the North End district. It was recommended by a lot of people for having the best authentic Italian restaurants in the city. We were recommended to try one in particular, Giacomo’s and even though we arrived at 10pm, they still sat us for dinner.

The food was incredible and it was very, very authentic Boston-Italian. The restaurant itself was tiny with around fifteen small tables maximum and seemed to be a family-run establishment. I had seafood pasta (when in Boston you have to have seafood, right?) washed down with some white wine.

For breakfast on Saturday morning we headed to The Friendly Toast which had also come recommended, but when we got there it was almost a two hour wait for a table and we were quite hungry. We stumbled across City Table which was a more up-scale place for breakfast as it was attached to the Lenox Hotel next door. The food was great and a very nice spot for some Saturday morning breakfast and coffee.

When we had arrived on the Friday we had walked through Chinatown to get to our hotel. There were queues forming for a lot of the restaurants on the Friday night so we said we would come back and try it.

We ended up in Gourmet Dumpling House which has fed the likes of Kate Hudson, Michael Douglas and Anne Hathaway. It’s also another very small and cramped restaurant with the owners not speaking much English so you get the full authentic feel of being in China for a while. We only ordered two items as the portions were huge and of course tried the dumplings.

What to see in Boston, Massachusetts

On the Saturday morning we roamed about the city, taking a walk along Boston Commonwealth (somewhere I wouldn’t mind living), through the park and around Acorn and Chestnut streets.

Around the park is also the Cheers bar where we went and had a pint in the TV set bar which is shaped like the bar from the TV show itself. There’s a bar downstairs where the idea originated from, but for the actual Cheers TV experience, I would recommend heading upstairs to the main set bar.

We took a walk from the Cheers bar around different parts of the city center, stopping at different monuments and statues along the Freedom Trail as it led us into the city. There was also an Irish Famine memorial in the middle of the city center which gave a great insight to me about how the people of Ireland were treated when they first started emigrating to America. Thank God it isn’t the same today and is quite the opposite with every American claiming to be at least 5% Irish.

We then ended up around the markets area. Taking in Quincy Market and Faneuil Hall Market where I would definitely recommend grabbing some food. We sampled some clam chowder (I think that’s a big thing in Boston) and it was pretty delicious. We then strolled along the marina from here while the sun was setting and made our way to the Envoy Hotel for their Lookout rooftop bar.

The rooftop bar gives stunning views of the city’s skyscrapers, especially at night. It was pretty chilly but they have heaters by each sofa so we weren’t cold for long. Plus the gin helped to warm us up.

Visiting Harvard

It’s super easy to visit Harvard University if you’re visiting Boston. The university is only a 20 minute train ride outside of the city center in Cambridge, Massachusetts.

To be honest, there’s not much to see at all. The town of Cambridge is rather nice if you want to grab a coffee or stronger drink. There are a lot of tourists and merchandise shops in the area. But the university itself is nothing unlike Queens in Belfast. Trinity College in Dublin would probably be nicer to visit.

As it was the Christmas break there weren’t any students around. So the place was quite deserted and just busy with tourists. Of course, I got my Elle Woods photo. But wasn’t keen on queuing behind 50 people for a photo with a statue of John Harvard himself.

A trip to Salem

Probably the most exciting part of the trip for me and one that was least expected, was getting the train out of Boston at 9am on the Sunday to visit the town of Salem. The trip took 45 minutes in total and was very easy to get to.

When I was younger (and now, who am I kidding?) I was so interested in witches, magic and ghosts. Hocus Pocus is one of my favourite movies of all time. I always had this intrigue in what happened with the Salem Witch Trials all those years ago.

Visiting Salem was something I was able to tick off my Life Bucket List. Something I never actually thought I would ever do. It wasn’t as creepy as I expected it to be. After all, it is 2020 and we don’t live in those times. But most everywhere was witch-themed and there were lots of trinket shops dotted around.

It’s a very small town so we visited the Tourist Office and the Salem Witch Museum. I’d really recommend the tour to understand the actual history. And then on to visit the Witches House and Witch Village.

We ended grabbing a pint and some Irish stew in an O’Neill’s pub not far from the Witches House. Watching the Liverpool game with some traditional Irish music being played in the corner. When in Salem, eh?

Boston, Massachusetts: yay or nay?

I would definitely recommend Boston as a place to visit, but I probably wouldn’t go for longer than a weekend. Since Harvard and Salem are so close by, I would also recommend giving them a visit too. Even if to just see more of Massachusetts.

One thing to note about Boston is to bring your passport for ID in bars and restaurants. It’s a very student-orientated city, they don’t accept drivers licenses as ID as they can be easily faked.

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