Trip to Boston in December
- Kimi's Travel Thoughts
- 4 days ago
- 10 min read
As 2025 came to a close, I had the opportunity to take a work trip to Boston, Massachusetts. This is a trip that I likely would've never taken on my own because I try to avoid traveling north during cold weather months. However, I was going to a conference that I was super excited about and decided that braving the cold would be worthwhile and it would be nice to have some time to explore an area of Boston that I hadn't ventured around before!
For this blog post, I'll break things down by sharing some of the travel logistics followed by a day-by-day recap before wrapping things up.
Weather
I'm not one to travel north during the winter months, but I figured it would be okay for this work trip. The weather started to change for, in my opinion, the worst. There was a winter storm on the way and I don't really own clothes for that type of climate. To stay as warm as possible, I wore a ski jacket, a scarf, and a beanie. I decided to dress in layers which helped with packing and bought a pair snow gloves before my trip because my $5.00 knit gloves from H&M were not going to get the job done. I also wore fleece-lined boots. When I arrived in Boston, I noticed that the locals were wearing similar articles of clothing with one key difference -- a parka. That longer coat is important for staying warm if walking outside a lot and was something I would have greatly benefitted from wearing if I had one. If you decided to travel to Boston in December or anywhere north during winter, bring a parka.
Flights & Lodging
I booked my flights and hotel during the Fall 2025 U.S. government shutdown, so I decided it was best to book everything through my company's travel agency in case there were any changes to my travel plans. During that time, I had a lot of concerns about potentially traveling during a shutdown and determined that would be a less stressful option.
My outbound flight was on Delta and it was my first time flying with this airline. I decided to create a rewards account because there are always added perks when flying by doing so. In this case, being a rewards member gave me access to free WiFi on the plane! My return flight was on Southwest and the weather caused some delays with my original flight, so I was rebooked for flight that was set to takeoff about an hour earlier. There were delays with that flight as well and the plane landed at the same time my connecting flight in St. Louis was supposed to takeoff. Fortunately, Southwest held the planes for those of us onboard because there were several connecting flights leaving around that same time and it would've been a lot of work trying to rebook a lot of passengers from my flight.
Pro Tip: Sign up for the rewards programs with any airline that you fly. Delta and Southwest offer free WiFi for rewards members at the time this post is published and other airlines have perks that come with being a rewards member. Also, I recommend downloading the apps on your smartphone for airlines that you fly because it's very helpful getting immediate notification of updates related to your flight along with access to your digital boarding pass.
Getting Around
My primary mode of transportation was walking. Boston is a very walkable city and wanted to take advantage of that while I was visiting. In my previous trip to Boston, I actually took the public transit to get around. I wasn't going to have time to explore as much of the city during this trip, so I opted to walk around the Seaport District where I was staying for the conference and used Lyft to get rides to locations that were just outside of a reasonable walking distance.
Trip to Boston in December by Day
Since this trip to Boston was for work, my time was primarily spent at the conference. However, I had some time each day to explore the Seaport District which is the area of Boston where the conference was hosted. I was committed to making the most of this trip with the time I had!
Day 1: Faneuil Hall & Quincy Market
I flew to Boston the day before the conference was set to start due to availability of flights. That worked in my favor because of a winter storm happened to be making its way from the Midwest to the Northeast during my trip and I had some additional time to checkout the city before conditions worsened. My hotel room was ready just as I got off the plane, so I went directly to my hotel room to settle in, check my email for work, and then determine where to go for sightseeing and dinner before it got dark. After checking out the GPSmyCity app for some inspiration and seeing one of the recommendations that my colleague also gave me on the travel articles I was reviewing (shout out to my fellow travel bloggers), I decided that Faneuil Hall Marketplace and Quincy Market would be the perfect location!
I caught a Lyft to Faneuil Hall and immediately took photos of the beautiful Christmas tree outside. Then, I began to walk around to scope out the shops and came across Pepper Palace -- a business specializing in hot sauce. If you have been keeping up with my blog, you know that I love hot sauce and have referenced it in my travel from home tips and even wrote a post dedicated to my first time attending the hot sauce festival in Austin. I couldn't resist going into the store and I was warmly greeted upon entering. Hot sauce fans are passionate people and want you to find a sauce that you can appreciate. I began tasting a variety of sauces in the store and used their buy 3, get a fourth item free deal. The best part? They offered a $5.00 USD flat rate shipping fee which means they were able to box up and mail all the sauces I purchased! Pepper Palace knows they get a lot of tourists and were prepared to make it easy for everyone involved to complete transactions.
Then, I went inside Quincy Market to find something to eat. This food hall is gigantic and there were so many options to choose from. I walked in knowing that I wanted fish and chips, and came across The Fisherman's Net. Their fries were as delicious as advertised and my fish was hot, flaky, and paired perfectly with the tartar sauce. After eating, I looked through some of the vendor stalls before going to a new pop-up bakery location called Lizzie's Pop Up Bakery and got a slice of snickerdoodle cake before getting in a Lyft to return to my hotel. Sunset begins around 4:00 PM in Boston during this time of year and I was ready to wind down after a long day.
Day 2: Conference Begins & Legal Sea Foods
My second day in Boston was the first day of the conference I was attending. Lunch was on our own this day, so I walked to a nearby Dunkin' for a breakfast wrap, hash browns, a hot latte, and some blueberry glazed Munchkins that I planned to have as a snack later on. I couldn't be in Boston for multiple days and not go to a Dunkin' for coffee and donuts!
I collected a lot of items and opted to walk back to my hotel before going to a group dinner at Legal Sea Foods. It had been raining all day (Boston wasn't quite cold enough for snow from the winter storm) and I ended up walking back in less than ideal weather. After drying off and warming up at my hotel, I opted to catch a Lyft for a 2-minute drive to Legal Sea Foods - Harborside where I met up with my dinner group. For dinner, I ordered the sole and opted for lemon butter with capers as the finishing sauce and chose crispy potatoes and broccoli for my sides. This was my second time eating at Legal Sea Foods (I ate lunch at a different location during my first visit to Boston many years ago) and the food was once again delicious. Boston is a place with access to fresh seafood and I made it my mission to enjoy fish for my meals as often as possible.
Day 3: SNOWPORT Holiday Market
The third day of my trip to Boston was a busy one with all day programming set for the conference. We wrapped up in the early evening and I was trying to decide on what to do for dinner. I kept hearing people mention that the SNOWPORT Holiday Market was within walking distance of the conference center and something to check out. One person I met at the conference told me she was going there as she was on her way out the door for the afternoon. I realized that the evening would be my last opportunity to check it out before I had to return to Texas, so I made the short walk in the frigid temperatures after attending a final session for the day. It's a good thing one of the vendors had hand warmers as their giveaway items because I certainly needed them that night!
I walked around the giant marketplace and appreciated the photo spots, the variety of vendors, and the signs at each vendor's stall that included the hometown of the artisan or business. I saw some businesses from Faneuil Hall (including Lizzie's Bakery) and came across a stall for a local non-profit called More Than Words which focuses on empowering local youth and providing them with education and resources that set them up for a sustainable future. They had many books for sale, and I chose to buy a copy of The Night Before Christmas because the one they sold was illustrated by Hayden Goodman, who is a Black illustrator from Massachusetts. That was a great opportunity for me to support multiple local entities and people in a single purchase.
It was dinnertime and I was getting pretty hungry, so I walked to the other side of the market to check out the food vendors. Once again, there was great variety and it was pretty tough to make a decision on where to get food from. It was literally freezing outside and the wind chill made it feel like it was probably in the teens or low 20s and that made me want some comfort food. There was a food truck called Cheese Louise which serves up gourmet grilled cheese and that matched the type of comfort food I was in need of. I got the baconator grilled cheese with a side of chips. It was warm, gooey, and light enough so that I could get food from another vendor. I walked over to the Dumpling Daughter stall and got the pork and scallion dumplings. After eating my dumplings, I walked around the market for a few minutes and took some additional photos. Then, I took a longer, scenic route back to my hotel so I could walk around to see more of the Seaport District at night.
Note: I have a dumpling series on Instagram where I post photos of "pocket food". Be sure to follow Kimi's Travel Thoughts for that content and more exclusives so you can see all the photos that don't appear in this blog post!
Day 4: Exploring the Seaport District by Foot
I had another early start for the last day of the conference which would conclude at lunchtime. So, I dropped my luggage off in the luggage storage at my hotel and set out for the conference center where breakfast was being served. After the conference came to a close, I had a few hours to spare before I needed to leave for the airport. It was still really cold as it had been all week, but I grabbed some extra hand warmers and decided to just walk around the Seaport District with the time I had left in Boston. As I was riding back from Faneuil Hall earlier in the week, I saw some great locations to visit and take photos that I noticed were within walking distance if I ever had some extra time for the journey.
It was too cold to have my hands exposed and my gloves were a bit difficult to use with my phone, so I ended up walking around without using navigation to guide me. Instead, I just occasionally checked the map on my phone to see what streets were nearby and play some Pokémon Go along with way. I ended up outside the Boston Children's Museum and took some photos of the skyline from the boardwalk. I also took photos of the iconic Hood milk bottle building and photos of the Boston Tea Party Shop and Museum before making my way to the other side of the boardwalk to walk back into the Seaport District. I stopped in a neighborhood market for a bottled smoothie before returning to my hotel to grab my luggage and work on a couple of items for work before going to the airport.
Wrap-Up
Getting home was a bit chaotic with the flight delays and rebooking, but I was happy to return to Austin after a fun, busy, and exciting week in Boston! During my trip to Boston, I got to learn new things, see different areas of the city, and experience activities that you can only really do in Boston in December. I ate delicious seafood and and settled into the colder environment. It never got above 40 degrees Fahrenheit and the wind chill kept the "feels like" temperature at or below freezing each day. Needless to say, returning to Austin at night where it was about 43 degrees actually felt on the warmer side and I was comfortable only wearing the liner of my ski jacket rather than the full set.
Traveling north during the winter is tricky because winter storms are always a possibility, but I got really lucky during this trip and the snow never appeared in Boston until I was on the plane preparing for takeoff to return home. However, there's something so special about traveling to cities up north during the holiday season and it feels magical! I never saw myself taking a trip to Boston in December, but I'm glad I did because it was truly a great experience.
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