I love the thought of New England in the fall or early winter, so I decided to make that trip happen for my 28th birthday. I picked a weekend close to my birthday, made sure my family could go, and we were off for a long weekend in Boston! Planning our itinerary was actually more difficult than I thought it would be; between juggling all of our different likes and dislikes, trying to be frugal, and the fact that what I really wanted to do was just be there and observe everything, I think I did an alright job!
Thursday night we landed and got settled into our AirBnB in Brookline. Heads up – Brookline looks far on a map, but it was surprisingly close to everything. We Ubered or walked everywhere, so I can’t vouch for proximity to public transit. I saw it close by, but can’t speak from experience.
Our Long Weekend in Boston
Friday
Friday morning we headed off to Sam Adams for a brewery tour around 11 am. The tour was actually better than I expected; the guide was just corny enough, it was just educational enough and we got to drink a considerable amount of free beer! Upon recommendation from the tour guide and a local, we headed to Doyle’s Pub straight after. They have an agreement where you get a free Sam Adams official pint glass with your brewery tour ticket! Fortunately, the food was also delicious. We ordered lobster mac n cheese, lobster rolls and clam chowder. When in Boston, you know?
Full and ready to explore, we made our way to the Boston Common Visitor Center to start the Freedom Trail tour. Between one thing and another, we decided to go the self-guided route, with a map and guidebook. At the beginning, I would guide us with the map while my sister Karla would read us the guidebook. It’s a really long tour though, so that ended after about stop 10. I love history and don’t mind walking, so I would recommend the tour. The booklet and map cost less than one guided ticket, so it’s definitely worth the savings. That said, it’s a ton of walking and at some point, your brain stops absorbing information and the statues and wall plaques kind of blend together.
We took some small detours and ended up in Charlestown at sunset, after about four hours of walking…and we didn’t even technically complete the whole tour. After lots of family photos at Charlestown Navy Yard and enjoying the view, we grabbed drinks and food at a local pub and headed home.
Side note: since Middle School I have been extremely interested in learning about The Holocaust. I love reading about it, watching documentaries and visiting museums. I try to go the Holocaust Museum in every city I visit, so as soon as I found out they had the Holocaust Memorial in Boston, I made sure we walked past it. It’s actually along the Freedom Trail as well, but I’ve included photos separately since it’s not part of the trail. Considering the space they were given, I think the memorial is beautiful. The way they memorialize the different camps, all the lives lost and the symbolism up to the sky with beautiful glass was gorgeous.
Saturday
Another heavy walking day, we first stopped at Fenway Park to walk around and explore. Full disclosure – we are not baseball fans. Nothing against it, but none of us follow baseball. So while Fenway is obviously an institution, we voted and skipped the tour. Instead, we walked around, going into the famed Bleacher Bar to see the field and walking all the way around, seeing the statues and Yawkey Way. There was a game another day we were there and driving by I could tell that whole experience was awesome. I’ll have to do it next time!
We grabbed brunch at a locally recommended place (nothing special) and then went off the Cambridge for the Hahvahd Tour! Led by current students, the Hahvahd Tour includes actual facts and funny, random anecdotes you may not get on a school sanctioned tour. It was nice to see from a student’s honest perspective and of course, it’s a beautiful campus! I will say, the undergrad campus didn’t have the grandeur I expected, probably because Cambridge has become more city than college town?
From there, we headed to South Boston (admittedly a bit of a trek) to visit Boston Harbor Distillery. They’ve been distilling local spirits that couldn’t be classified as rums or whiskeys due to some regulations. They now have moved to making some [read: STRONG] whiskeys, rums and some delicious liqueurs. I genuinely don’t remember how I came across BHD, because it was hard to find and our Uber drivers had never heard of it. I love supporting local business and trying new booze, so it was a win-win! If you’re ever looking to host a small event in Boston, their location would be ideal!
We headed to Union Oyster House in Haymarket for dinner. Thankfully we got there early-ish (and before we were hungry) and only had to wait about 45 minutes. We’d anticipated the wait, so we grabbed some drinks at the bar and watched a football game. We ended up being seated across the way from JFK’s old personal table, which they still seat! Then when the food came…there are not words. Fish chowder. Clam chowder. Lobster ravioli. Mussels. Fried calamari. Oysters Rockefeller. Some really yummy cornbread. Y’all. Seafood normally doesn’t fill me, but it happened. Honestly, the best fish chowder and clam chowder I’ve ever had in my life. They brought my Boston Cream Pie for desert and sang Happy Birthday, but it turns out Boston Cream Pie isn’t my thing. Sorry, not sorry. Still though, best overall dining experience (because fam) I’ve had in a very long while. [Terrible lighting though. Apologies in advance for these photos.]
Sunday
Sunday was a bit of a lazier day, as it was gloomy and raining. We started with brunch at Earl’s Kitchen + Bar in the Prudential Center, mostly because we have an Earl’s in Miami, so we knew it would be good, and that way we could walk around during the rain. I hadn’t really eaten before that, so my brain wasn’t fully on, otherwise I would’ve taken pictures of the restaurant. It opened recently but oh my gosh. I’ve never found a restaurant so cool, modern, and aesthetically pleasing. It was like someone took my design style and created a restaurant just for me. [Go look at their Instagram.] It didn’t hurt that the food was delicious, but mine wasn’t a photogenic dish, so there’s no visual proof. Sorry!
Once the rain cleared, we walked around Copley Square, went into Boston Public Library and continued making our way through Newbury Street, to Boston Public Garden. Despite the muggy day, it was really an easy, lovely walk. We made several remarks about how if Karla lived here, she would run here with her dog. We walked north out of Boston Public Garden over to Beacon Hill, a neighborhood known for its older buildings and some cobblestone streets, particularly Acorn Street. This is what I always imagined Boston would look like!
It started to drizzle a bit again, so we headed to Harpoon Brewery to try their beers and hang out. We didn’t do the tour, but they have a really big bar and seating area, so we settled into the bar with some beers and a delicious pretzel! For those who aren’t aware, Harpoon also makes UFO beers, so we were able to try a bunch of their different hefeweizens. They were also amazing. From there, Erika had to head to the airport, so the rest of us walked over towards the harbor. Somehow we decided we wanted to walk to Whole Foods for dinner, so we trekked past South Harbor, through Chinatown and the Financial District to get there. After that, it was another quiet night in.
Monday
It’s a good thing we got all the major stuff done the first few days, because Monday was rainy, muggy and gloomy all day. We walked over to Tatte Bakery in Brookline for breakfast and got drenched walking back to the AirBnB! It was worth it though, the place was adorable (and packed at 8 am on a Monday), the food was delicious and the walk over was nice too. [Note: the picture below is their Shakshuka, which my mom and sister ordered. I ordered a challah bread breakfast sandwich which was yummy but not pretty.]
After freshening up, we went to the Fall Opening (meaning free entrance!) to the Museum of Fine Arts. Admittedly, we aren’t really museum people, but it was a neat thing to see since it was free. The range of art they have is huge and a bit random, but impressive. Lunch for the day was at Joe’s American on Newbury Street. It was a little more upscale than we’d expected, but good nonetheless. Their soups were delicious! We ended the day walking to Blackbird Doughnuts, because they came highly recommended. Full disclosure: the location was cute but the donuts were just fine. Not great. Then again, I’ve been to Salty Donut in Miami, Doughnut Plant in NYC and Five Daughters in Nashville, so my standards are pretty high. It ended up being the perfect rainy evening to hang out and watch a movie (or two).
Tuesday
Tuesday was our last day, so we walked to Brookline Village for breakfast. There was a very cute, picture-perfect coffee shop we’d planned to visit, but the menu wasn’t great and we were in the mood for real food. A block further was Martin’s, a traditional-style, hole-in-the-wall diner. It was delicious! After breakfast, we packed up and headed to town. We ended up perusing Target and making our way to Long Wharf, sitting at the Joe’s there for a beer before heading to the airport. We had time to kill, but were lugging our suitcases around, so we couldn’t really do too much.
Fortunately all our flights were within an hour of each other, so nobody had to linger too long at the airport! Looking back on the trip, I feel like we did a lot, but it was definitely a different experience than when I travel alone. We slept in and took our time in the mornings and took more time to spend together as a family in the evenings rather than stretching the days and really squeezing everything into them. It felt more like a family vacation, which I’m incredibly thankful for. As with most cities I visit, I left wanting to come back, but there’s so much more to see! I think I squeezed enough out of Boston for the time being, but who knows! Maybe I’ll visit again sooner rather than later. One long weekend in Boston isn’t enough!
Long Weekend in Boston: Overall
The more I travel, the more I realize I absolutely love older, historic cities. Boston was that and more. It’s also definitely a city worth visiting during every season, I could do a long weekend in Boston four times a year!
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