A Beer Loving Boston Vacation

A Boston Itinerary Designed for the Beer Lover

This summer, I visited Boston, Massachusetts for the first time in nearly twenty years. With such a time gap and age difference since my previous visit, the developed itinerary was definitely that of a (essentially) first time visitor. I made sure to incorporate activities tailored to my specific interests plus some touristy must-dos. Below, I have detailed my exact itinerary of three days in Boston with details about what I most enjoyed, what I would do differently, and what I would like to do on a future visit.

Day One

We checked in early to our hotel: The Residence Inn Boston Cambridge located across the Charles River from downtown Boston in Cambridge near MIT. I am a Marriott Bonvoy Boundless credit card holder, which grants me both status with the brand, but also an annual free night award, which I applied to this reservation. This is one of their lower level cards with a $95 annual fee, which the free night award more than covers. Message me if you'd like a referral for this card (I would benefit from it).

For destinations like Boston where I will not be spending a lot of time at my hotel, I care about a clean, safe hotel with a convenient location more so than a more luxurious hotel or one with amenities. The Residence Inn Boston Cambridge absolutely fit these standards, and was only a 5 minute walk to the Red Line of Boston's subway system known as "The T", which goes right into downtown.

Acorn Street -- Beacon Hill, Boston, MA

First stop was Blackbird Doughnuts, which enjoted in Boston Common before exploring the historic Beacon Hill neighborhood. Acorn Street in particular is a must stop for some photos and to admire the charm of this area.

While in Beacon Hill, we visited Beacon Hill Books & Cafe, which is one of the most aesthetically pleasing bookstores I have ever visited. However, I was disappointed the selection was entirely new books because I greatly prefer shopping used.

From here, we fixed that and visited Brattle Book Shop. The quantity of books here is so large that they even have a whole lot's worth of shelves outside the shop. However, I found the selection to be rather dated without many titles I was interested in.

Brattle Book Shop

Lunch was enjoyed at Tora Ramen, a recommendation from my little brother living in Connecticut. I was surprised when it was cash only, so be prepared if/when you visit.

I love a post meal walk, so we strolled through Boston Common where I admired Trillium's Garden on The Common from a distance. I absolutely need to stop here on a future visit.

We then rented bikes using BlueBikes, Boston's citywide bike share system. An Adventure Pass with unlimited two hour trips in one 24 hour period is only $10. I always travel with my own helmet if we have plans to rent bikes.

Trillium Brewing Company - Fenway

We biked part of the 25.5 mile Charles River Bike Path heading west. At our halfway point, we detoured to visit Notch Brewing in Brighton, but we didn't check their hours and it was closed. Will plan better next time! The path was noticeably in better shape on the south side of the river. The north side of the river's path heading back into Cambridge was extremely uncomfortable, and I would skip it next time.

After dropping off our bikes and a quick shower at the hotel, we headed back into Boston for a Red Sox game. Despite being a diehard Yankees fan, visiting Fenway Park has long been on my bucket list as a true fan of baseball.

Samuel Adams Wicked Fenway IPA at Fenway Park

With some time before the game, I checked off a major bucket list brewery: Trillium Brewing Company at their Fenway location located a short walk to the stadium and next to TimeOut Market Boston. TimeOut Market will even deliver food to you at Trillium Fenway. I cannot recommend enough getting beers at this beautiful indoor/outdoor taproom before a game. The beers are cheaper and higher quality than those at Fenway. Trillium Fenway is not to miss even if you don't have baseball tickets!

And seriously, even if the Red Sox are your enemy, as they are mine, a game at Fenway Park is iconic. The stadium is like nothing else still in existence. Even I could appreciate the love these fans have for their team. Don't miss the whole stadium participating in "Sweet Caroline". Ignore the chanting of "Yankees Suck" no matter the opponent.

Day Two

Since we still were within the 24 hours of our BlueBikes Adventure Passes, we rented bikes and completed a section of the 16.1 mile Emerald Necklace bike loop ending in the Jamaica Plans neighborhood of Boston. This route had several interruptions and was quite disjointed. I would want to do either a different section of this ride in the future, or at a time when the route is more cohesive.

For lunch, we enjoyed the most delicious breakfast sandwich of my life at Mike & Patty's and then walked to the Samuel Adams Boston Brewery for a tour and some beers in their taproom.

Sam Adams Summer Ale in the brewhouse.

Sam Adams offers several different tour options. I selected their most basic Signature Experience for only $10 and I absolutely recommend it. At one point during the tour you basically get unlimited amounts of the Boston Lager and Session IPA easily offsetting the $10 cost right there. The guide was both friendly and informative, and even as someone with some knowledge of beer, I still learned a lot.

Don't skip visiting their taproom after the tour. I enjoyed a flight of some of their taproom exclusive beers, including some beer/wine hybrids, and was quite impressed. These beers are definitely a step up from what you typically see from Sam Adams elsewhere.

After the tour and taproom, we took the train to Newbury Street, a well-known shopping street in downtown Boston with local small businesses, larger chain stores, restaurants, and some higher end boutiques. I did not know this ahead of my trip, but clothing is exempt from sales tax in Boston on items up to $175. I enjoyed browsing stores that I had only ever shopped online like Sezane and Buck Mason. I enjoyed my first Two Chip Chocolate Chip Cookie from Levain Bakery, and I found my favorite bookstore in Boston Trident Booksellers & Cafe.

Trillium Brewing Company - Fort Point

Shopping was followed by more beer at Trillium Brewing Company's larger Fort Point location. This location offers small 5oz pours allowing you to try many options from their extensive draft list. We had so much fun drinking beers here that we cancelled our dinner reservation and ate here too. The mac and cheese was fantastic, but next time I do also want to make it to where our reservation had been: Row 34.

We closed out the night by visiting nearby Fort Point Market, which had a good selection of local craft beer, especially available to purchase as single cans. I was able to buy a couple of beers from breweries that we did not get a chance to visit on this quick trip. Read how I take home craft beer here.

Day Three

The Boston Athenaeum

Our last day visiting Boston was our most touristy day visiting and learning about this revolutionary city's rich history.

While very touristy, I really enjoyed our Freedom Trail tour beginning and ending at Boston Common. Led by a "patriot", the 90 minute tour was informative, entertaining, and just flew by. It still left us the majority of the Freedom Trail for us to cover on our own later.

But before we could complete the Freedom Trail, we had a much-anticipated Art and Architecture tour at the Boston Athenaeum, an over 200 year old members-only library housing over half a million books, including George Washington's private collection. This guided, 60 minute tour is the most affordable way a non-member can explore this beautiful and historic space. Be ready to take many photos.

Cannoli from Mike's Pastry

For lunch, we walked the Freedom Trail to the North End neighborhood, Boston's Little Italy, where we tested our luck walking in without a reservation to the much-recommended Carmelina's. I would absolutely make a reservation in the future, but we accepted the 45 minute wait and walked across the street to the famous Mike's Pastry for a cannoli snack. Both the cannoli and our Italian lunch did not disappoint, but I would be curious to try both Modern Pastry and Giacomo's on a future trip as these places were also highly recommended.

We walked off lunch by completing the Freedom Trail all the way to Bunker Hill. I highly recommend taking the ferry back to downtown afterwards to give your feet a break.

Distraction & Democracy Beer Garden

To further give ourselves a break, we stopped at the Distraction & Democracy Beer Garden. I had not known of this place before arriving, but we had walked by it on our guided Freedom Trail tour earlier in the day. With a view of Faneuil Hall Marketplace, this outdoor venue is a great afternoon break on a busy day of sightseeing. It also let me check off trying two more Boston breweries at once. We did stop in Faneuil Hall Marketplace afterwards, but I thought it was underwhelming and skippable.

For our last night in Boston, we visited Lamplighter Brewing located walking distance from our hotel in Cambridge. I knew little of this brewery beforehand, but instantly felt like this would be my hangout if I were a local.

Lamplighter Brewing - Cambridge

I sampled several beers on draft and took some home to enjoy in the future. This brewery also has some of the most beautiful glassware, and I couldn't resist one as a souvenir.

For my last dinner in town, I grabbed takeout from The Smoke Shop BBQ to enjoy at our hotel while packing up after a fun (and boozy) few days in Beantown. After this short visit, I know there will absolutely be future trips to Boston, now officially one of my favorite US cities.

You've made it this far, so please tell me, what did I miss doing on this trip? Any specific restaurants, breweries (I sadly could not make it to LongLive Beerworks, but did pick up some cans), or favorite activities? I'd love to even get outside of Boston next time and it make it to some of the breweries in the surrounding area.

Please share in the comments your best Boston recommendations for my next vacation.