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How To Get the Most Out of Your Weekend in Boston

Updated: Apr 5, 2021

I’ve never been a very spontaneous person. I’ve tried to say that I am, but when it comes down to it, I like to lay my clothes out every night and book my plane tickets at least a month or six in advance. With that being said, I booked a weekend getaway with Anthony to Boston… set to leave the next day! I was so proud of my “yolo” screaming (in my head) self, I could barely contain my excitement.

It was pretty much fate that Anthony and I were going to Boston. It was the perfect flight at the perfect price and even included a hotel (which was pretty much free if I think about it. Thank you JetBlue!). What it failed to include was any layovers… honestly that was what sold me. I simply can’t say no to a nonstop flight. Literally everything was easy peasy. I could not have been more grateful… or ecstatic. So without further ado…

Where we stayed:

The hotel I picked through the JetBlue vacation package was, very properly named, The Revere (yes, like Paul Revere… “The British are coming”), located in the Boston Common. The reviews were typical, but when our Uber driver dropped us off we could not have been more happy with the place. Outside it didn’t look like much, but once you went inside it was completely decked out (tastefully, so very tastefully) with American Revolution art.

My favorite part was probably the light fixture above the lobby check in desk that was covered in old lanterns (“one if by land, two if by sea”… I know you got that without my explaining, I was just too excited). The hotel was a lot bigger than it looked when we first pulled up to it also (or we weren’t paying attention).

It had 25 floors, a nightclub, a pool with cabanas and a rooftop bar (surprisingly enough, if you google best rooftop bars in Boston, The Revere’s tops the list… TMYK). We probably would have gone and checked it out if our room wasn’t 6 floors above it on the same side…. did I mention our view was legit? Because it was. We hadn’t even made it out of the hotel and I was already loving Boston.

Where we explored:

While waiting for our flight, I stumbled upon the GoBoston Card, and was so glad that I did. With it, you pick how many days you want the card to be good for and you receive a list of places around Boston that accept said card. You can do as much as you want, the only stipulation is that you can only visit a place once a day; which was fine for us since we were only there for two and a half days. It was $79.99 a person for the two days, which does sound expensive at first thought. However, on the way home I calculated the cost of everything we did, and we would have spent $113 a person without the card. We barely even put a dent in the list!

The Mapparium –

Located at the Mary Eddy Baker Library, The Mapparium is a three-story, stained glass globe showcasing the world in year 1935. It was unlike anything that I’ve ever experienced. While there isn’t a whole lot to actually do, you kind of just stand there, it is still breathtaking. The globe is so vibrant and the acoustics were insane; you could hear a whisper across the room as if someone was talking normally. We, sadly, weren’t allowed to take any photos or videos of this experience, but you can read about it more here, if you’re interested.

The New England Aquarium –

This one is definitely geared more towards children and families… and it was the most crowded out of all of the places we went. But it was still very cool. They had a lot of marine life, from penguins to octopuses, jellyfish to seals. It was a lot of fun! And it’s right on the Boston Harbor, which is gorgeous.

Charles River Boat Cruise –

This was the most exhausting for us physically. We didn’t realize how long of a walk it was until it took us almost an hour straight to get from where we were at the Boston Harbor over to Cambridge. Got my FitBit steps in that day! The boat ride was great though. We got a commentary of the history, but it was really the view that did it for me. You take the turn out from where you meet at the CambridgeSide mall and see the Boston skyline and it was pretty much the whole reason I came to Boston (not really, but kind of). The cruise sails down the Charles River and stops at Harvard (Hahvahd) before turning back. The seats are a bit uncomfortable, so I’d suggest just standing the whole time. It’s a 70 minute ride, but it goes really quickly in my opinion.

Aside from that and visiting a few other places, we walked around a lot and tried to just see as much as we could. We walked the Freedom Trail without even knowing it,we made it to Fenway Park, the Public Gardens and saw the statue of George Washington. We visited the Old State House, the Old North Church (where Paul Revere hung the lanterns!), Faneuil Hall, The Boston Tea Party ships… I mean we really saw so much, it was incredible. And after all of that we still had time to fit in a show at the Improv Assylum, which was very entertaining.

Where We Ate:

When I think of Boston, there are certain foods that I feel like you need to try to get the authentic taste of being there. These were the items on the “Boston Bucket List” we didn’t even know we had: – Sam Adams Boston Brick Red – New England Clam Chowder – Lobster – Boston Cream Pie – A Fenway HotDog – Baked Beans

In no particular order of course.

We enjoyed (correction, Anthony enjoyed, I tried it but don’t have a taste for beer, ever) the Sam Adams Boston Brick Red at the famous Cheers bar. It was, naturally, very crowded but still a must to stop into on your explorations.

The Oceanaire

We were wanting to try the Lobster and Chowder at this restaurant called Neptune Oyster, but they are slammed all the time (makes sense, they come up everywhere for the best seafood in Boston) and don’t take reservations. So if you want to get a spot you need to go stand in line and get on a wait list when they open.

That was too much work for us since we didn’t have a lot of time, so we found our Lobster and Chowder at this place called The Oceanaire. It was actually recommended to us by an insanely nice couple we met at Emmetts Irish Pub. It was a bit pricey, but that is what I expected anyway.

The clam chowder was to die for. I could have eaten their whole pot. It came out at the perfect temperature and was so insanely flavorful. For dinner, I got the Mixed Grill which included Lobster, Shrimp, Scallops and asparagus. It was seasoned very nicely and everything was cooked perfectly. I’d definitely recommend checking out this place if you can’t get into Neptune Oyster. The Oceanaire also had a very local vibe and wasn’t crowded at all when we went, which was nice.

Mike’s Pastry

Mike’s Pastry is the place to get just about anything sweet that your little heart desires. It is slammed all the time and reminded me of the chocolate babka episode on Seinfeld (I don’t actually know why, it was a completely different situation). Anyway, this is where we got our Boston Cream Pie and oh my goodness, that shit was bananas. The custard was falling out of the pillowy cake layers and the chocolate on top was near perfection. I think I might have died and gone to Boston Cream heaven. Go to Mike’s, you won’t be disappointed.

Bleacher Bar

Being in Boston, we had to go to Fenway Park, even though Anthony is not a sports ball fan of any kind.

The Red Sox were out of town so we couldn’t catch a game (next time), but we did go into their eatery, Bleacher Bar, where you can look out into Fenway through a fence built into the bar. We enjoyed a couple of beers (cider for me… DownEast, which is their home brewed brand and wicked awesome! Check it out.), a hot dog that came with onions and nacho cheese on it (yum!), and we actually made it right as the Red Sox game started on TV. So that was a pretty cool alternative to making it to a game in the Park.

Boston Burger Co.

The last item on our list was baked beans. Apparently, from what I researched, not many places make authentic baked beans anymore. People tend to just cook them up in their own homes. However, our first night in Boston we went to this burger joint called Boston Burger Company, and they had some crazy ass burgers. Well baked beans came as a side, so naturally, that is what we chose. Anthony and I split the Whiskey Tango Foxtrot burger, which was messy, but good. I’m not sure how home cooked the beans were, but they tasted like it to me. Overall, I would call it a check off the list since they were the only ones we found.


All in all, Boston was one for the books and a really great “spontaneous” experience.

So tell me, what are you favorite places to go in Beantown? Is there anything out of the ordinary you can recommend for our next time there? Tell me in the comments!

And feel free to follow my adventures and come say hi over on instagram.

Looking to extend your trip in the North East? Check out my budget guide to New York City below.

Want help planning your own Boston getaway? Schedule your complimentary vacation planning call with Belest Travel Co here.




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