Blogmas Day 16: Holiday Getaway, Santa Takes Boston

This pre-Holiday Boston trip went through so many different stages, I can’t even remember what the original plan was. As it ended up happening, we dressed up like Santa and crawled our way from pub to pub, bar to bar, one Saturday afternoon and took in the festive Holiday vibes of the city. This was a much needed getaway and the last time we could probably afford to travel before the holidays. I say “we” but I do mean me. It’s almost time to be baking non-stop at my house!

Let me start off this blog by telling you about the Monday before our trip. Now, if you have ever driven to Boston, you know that there is no such thing as free parking. You either no someone or you try and park at one of the T stations outside the city for between $8 and $13. Well, the hotel we stayed at advertised a free parking package if you stayed between now and March 2018. I called them up to ask about this package only to find out that our reservation wasn’t on the books. Of course, this sent me into a small panic. I was looking at my reservation while talking to the woman on the phone. What happened? She explained that never updated the reservation on their end and we were listed as a “no show” for December 2nd. This sent me into a full panic because “no show” usually means you get charged anyways. Luckily, I didn’t. All of the issues had nothing to do with me. In a full panic now, I tried to keep calm and work with the woman at the hotel. We were able to get everything sorted but boy oh boy was that an issue I was not planning on dealing with on a Monday. Happy it happened a few days ahead of time though and not when we got to the hotel.

A few days later, it was finally the day of our trip.

Friday Night

Friday night, we got into Boston around 6:30pm. We lucked out and traffic was only bad immediately outside the city we work in. Getting onto I-84 from Hartford is always a mess. It was a nice ride up though, and much more relaxing than if we had tried to drive up Saturday morning. We checked into our hotel and relaxed for a few minutes before heading over to my cousin’s house to park the car for the weekend and spend some time with them.

While visiting, we got to play with their puppy, Wiley, and try out some local beers– I think I found a new favorite: Rose Ale.


The rest of the evening was relatively quiet and relaxing until Tim and I decided to head back to our hotel. We had a nice night time stroll through Harvard, joking about what kinds of people go there. After a couple of transfers on the T, we finally made it back our home for the weekend. We spent a bit of time trying to make the TV work before finally just falling asleep. Saturday was going to be a long day.



We started off the morning slow. We weren’t meeting up with friends until after 1pm so there was no need to rush around. We made our way to South Street Diner for some breakfast (so worth the wait!) before making our way to Government Center and Faneuil Hall for some pre-bar crawl exploring.

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Hot chocolate with fresh whip cream from South Street Diner

After our filling breakfast of the “Diner special” and Belgium waffles, we wandered around Government Center. There was a beautiful Christmas market set up outside City Hall that was made even better by the falling snow. We wandered through the dozens of shops, full of locally made items that would be perfect Christmas presents for anyone. Eventually, we stumbled across the ice rink at the center of the market. It had been set up to be a oval loop around some Christmas decorations with a tent near by where you could rent skates for a half hour. Near by, different companies set up little warming huts and charging stations for those attending the market. We grabbed a hot cider from one of the food vendors and then went to warm up in the Uber hut for a while. They had a cute set up with a fake old TV playing old videos of families in the winter with a “fireplace” to keep shoppers warm. Next door was one manned by Xfinity that housed a heater, comfy chairs, and a big screen TV. Not too bad, if I do say so myself.

After warming up for a bit in the hut, we walked through the snow over to Faneuil Hall to browse some of the shops. Window shopping is always a good time. Especially this close to Christmas! The displays are always so beautiful and interesting. Plus, being in Faneuil Hall meant getting to see their massive Christmas tree!

From Faneuil Hall, we decided to start heading over to the bar for check in. We found a street market on the way full of fresh fruit, fish, and other foods. There was something kind of magical about walking though in the snow and picking out fresh apples from a seller.


Street Market in Haymarket

After a while, it was finally time to meet up with everyone and check in for the bar crawl. Now, the deal with this crawl was that it was Santa themed. That meant that everyone participating all 2,600 people, were given Santa suits to wear. We donned our jackets, hats, and beards (the beards didn’t last too long. They were SUPER itchy and very smelly) and tried to see how many bars we could make it to. We started off at The Causeway while waiting for everyone to arrive. Tim and I helped ourselves to a few beers while watching others dance and scream along to whatever music was playing. Once everyone arrived, we moved to a bigger table and everyone downed a beer or margarita while we made a game plan.


Just a couple of Santa, drinking some Downeast Ciders and local beers.

Now, if you’ve never done a planned bar crawl, let me tell you something. Never make a plan. It won’t work, trust me. You can plan out what bars you want to go to and what you’re going to get well in advanced. That is great. I usually try and make a plan because I don’t want to stress about it later. This time though, any plans were going to be completely destroyed by the sheer amount of people and the snow. With 2,600 people and only certain hours you can be at certain bars, the lines were insane. The first bar wasn’t so bad just because we showed up towards the end of their scheduled time. The second bar was a much different story. We waited in line (and in the snow) for about twenty minutes before finally getting in. Inside was a sea of people. There was no way to get around without being pushed into another group of people. We made a valiant effort but gave up after just using the bathroom there.

The next bar was much more calm. We showed up, again, at the end of their scheduled crawl hours. That meant that the place was pretty much empty but the deals were still pretty good. We grabbed a couple of tables and a few drinks. We did some Ho Ho Ho shots and grabbed the drink special along with some dollar appetizers and relaxed for a bit. After the last bar and walking through the blizzard, we needed to just chill. I have to say though, the food here was incredible. Koy is a Korean fusion restaurant and for their specials, they included dollar cheesesteak dumplings, spicy wings, shrimp tempura, and pork dumplings. Everything was SO good. I’d go back any time!

From Koy, we headed back to Faneuil Hall since there were bars there that were a part of the crawl. We all pretty quickly decided that we didn’t want to wait in lines any more though and instead went on a hunt for food. Now, if you’ve never been to Faneuil Hall, let me explain it to you. The main building, known as Quincy Market, is full of different food stalls and little kiosks to buy souvenirs. It is a great place to go if you’re visiting Boston and everyone you’re traveling with wants to eat something different. They have chowders, Indian food, Italian food, Chinese food, state fair food, regionally themed food, ice cream, baked goods, and everything in between. If can be a little overwhelming honestly. But everything is so good.

The group split off to grab what we all wanted. A few of the guys went to get some seafood mac and cheese; Callie and I wanted cheesy fries and corn dogs; the other girls went for chicken tenders and fries (can you tell we had been at a bar crawl?). After filling up on our random foods, we headed off to explore around Faneuil Hall. We ended up at the Pepper Palace where the boys did something a little extreme. Now, the Pepper Palace lets you try out their sauces before you buy. You can get a chip and put some sauce or salsa on to try out. They have one sauce though that is so hot that you have to sign a waiver in order to try it. The boys did.

Everyone who was in the shop stopped to watch Tim and Noah try out this sauce. Watching them both immediately start sweating and turning red in the face was enough to make everyone laugh but also show some mild concern. Being a good girlfriend, I bought Tim his favorite chocolate ice cream afterwards to soothe his mouth since I didn’t think that licking snow was going to be a great idea….

The night finished with some ice cream and photos at the Christmas tree. It may have been an early close to the evening, but it had still been a fantastic day.


Sunday was another chance for us to explore the city. After dealing with some issues trying to get an Uber that morning, we made it to Somerville to drop our stuff off in my car. With everything dropped off, we headed into Harvard Square to grab a bite to eat. On the recommendation of my cousins, we went to Felipe’s for lunch. Everything was so incredible. Tim got a chimichanga, I had a quesadilla, and we split some churros with dulce de leche. It was all so good!

From the restaurant, we made our way to the Museum of Science. Tim and I both love science and museums, in one form or another– I even work at one. We arrived around 2pm, just in time to check out the lightning show in the Theater of Electricity.


We continued to explore, taking in the science of mental health; the wonders of the human body; and the science behind football. If you’ve never been, I have to high suggest this museum if you love getting to interact with science and how the world works.

At the end of the day, as the sun set, it was time to finally head home. All I can say is that I can’t wait to be back!


Let me know about your holiday adventures in the comments! Where is your favorite city to be in during Christmas time?



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