“We’re here for a good time, not for a long time!” That was our motto during our recent trip to Beantown. When Southwest has a good deal, you must strike when the iron is hot! So without much of a plan, other than to sample the new Chase Sapphire Lounge in the Boston Logan International airport, we locked in our flight to Boston with little more time than a long layover to spend in the city.
Our flight left Baltimore at 7:40am and touched down at 7:40pm later that same evening. It left us about 8 hours with feet on the ground to eat and drink as many Boston staples as our bellies could handle.
Getting From the Airport to Downtown
There is probably no element more crucial than efficient transportation when it comes to leaving the airport on your layover. You want to be able to get out and get back in quickly in order to maximize your time in the city. The Boston Logan International airport is perfectly suited for a layover as it has easy access to the subway from the terminal.
You’re going to want to hop aboard one of the free buses that shuttle you to the nearest subway location – Airport Station. Once you arrive at the station, you can purchase a subway ticket for $2.40 (at the time of writing). We went ahead and bought round trip while we were already standing at the machines to save time on our way back to the airport. After your ticket is in hand, follow the signs for boarding the inbound train which will take you to downtown Boston.
For our itinerary which mostly centered around the north end, we exited the subway at State station.
Breweries to Visit on a Layover in Boston
Samuel Adams Downtown Boston Tap Room
No beer lover’s visit to Boston would be complete without paying homage to Samuel Adams, so we did our due diligence by stopping in for a quick brew. We arrived around 11:30am just as the doors were opening and grabbed two seats at the street-level bar. The bartenders, friendly and helpful, unlike what you might expect in most touristy destinations. As true beer fanatics, we would have rather gone straight to the source at the actual brewery, but during a layover, time is of the essence and the nearby tap room location delivered nonetheless. With a wide selection of exclusive beers on tap, picking just one was the toughest part of our day. For me, a sour and for Matt, a coffee porter. When your beer is derived from fruit and coffee undertones, it makes justifying your pre-lunch indulgence that much easier.
Trillium
After a short walk across the Evelyn Moakley Bridge we found ourselves in the South Boston Waterfront neighborhood. The walk alone would have been fulfilling, but it was Trillium that had our cups overflowing with goodness. Unlike Sam’s, it was obvious that this brewery was one that also attracted the locals. Downstairs was a bit rowdy but upstairs, the seated bar was a quiet spot to enjoy conversation with your date. With an extensive beer list we did our best to not overindulge. Matt was happy with his hoppy selection as I savored my sour. We “wowed” as plates of food were dropped off to our neighbors at the bar and if an entire sea of mollusks and crustaceans weren’t already taking up residence in our stomachs, we easily could have been enticed to order an app or two.
Before we asked for our check, we caved and selected a barrel-aged brew to share. It would have been easy to sit and sip the afternoon away, but planes don’t wait for anyone, especially not tipsy travelers.
Harpoon
This one was on our list, and if we had another hour or so, we probably would’ve popped in for a quick pint. If you have more time for brew hopping during your long layover in Boston, consider adding Harpoon Brewery to your itinerary.
Must Have Bites During a Layover in Boston
Coffee & Pastries
You simply can’t go to Beantown and not include beans in your itinerary. That would be foul play. Neither one of us wanted to sacrifice precious seafood space for baked beans, green beans or even jelly beans – so we did what any good caffeine addict would – we justified coffee as our checkmark for beans. There are no shortage of places to sit down and grab an espresso, a cappuccino or a good old-fashioned Americano in the north end of Boston.
Time was already ticking and we had to pick just one and so we wandered into Caffe Vittoria, where we were enamored with the displays of old-fashioned coffee grinders as much as the aroma of coffee that spilled out from its doors. Knowing there was much to eat in our near future, we passed on the pastries, but doing so was a challenge with Boston cream pie and tiramisu on the menu.
If you arrive just a wee bit later in the day than we did, you can sip on one of their specialty adult coffees mixed with a variety of liqueurs. Or better yet, pop into the cigar lounge and order up an amaro.
Whole Belly Clams & Raw Oysters
Once we were fully caffeinated, we made a beeline to the nearby Boston Public Market. We walked at a pace that might have suggested we were on some kind of Amazing Race, the feed-your-face edition. Matt was ready to slurp back some raw oysters and the indoor market filled with artisanal vendors was one of the first in the area to open its doors to the hungry Saturday morning crowd. Unfortunately, while the donut stand was up and running and the coffee machines were in full swing, Red’s Best – the seafood counter – didn’t open their kitchen until a little later in the day. With no time to waste, we frantically circled the market, soaking in the sights and hoping somehow time would match our step. It didn’t and so we did the next best thing. The tourist thing.
I quickly searched for anything else in the vicinity shucking the shelled creatures to appease my husband’s now rumbling stomach. The answer was Union Oyster House – America’s oldest restaurant, which is located on the Freedom Trail. Inside, we grabbed the last two empty stools at the very angular raw bar.
When Matt questioned the unusual geometry that required a stack of coasters to level out his plate, the bartender happily obliged us with a bit of history. The tilt of the bar was for the then much shorter men passing through to belly up to while they enjoyed their meal. The angle allowed for any resulting debris to tumble onto the floor, away from the oysters, where it could easily be swept up later. While we were sitting there, we placed an order for whole belly clams, checking another item off our Boston wish list. If you’re on a budget, make sure to ask about the market price. Our bill was a bit pricey, but the clams were decidedly one of the best bites of the day.
War of The Cannolis in Boston
Long gone are the days where we ran the streets of Florence like little feral tourists in search of the best bites, but chowing down on cannolis in the north end of Boston transported us right back to our summer in Italy. Mike’s vs. Modern – it’s the cannoli conundrum each sugar-starved shopper is faced with. Which to choose? Depending on who you ask the answer is sure to vary. There were reports of a crunchier shell or a creamer filling. One was geared towards the tourists while one better served the locals.
After trying both and wiping the sugar rims from our lips, we determined there was no clear winner. Mike’s cannoli was noticeably larger, but we paid for the difference in size at a whopping $7.00 for just one. Modern’s rang up as $5.00, a more modest fee for the comparably petite roll. Our vote – go for whoever has the shortest line when the craving strikes.
Lobster Roll & Clam Chowder
Quincy Market. Did we lose you? Okay, okay hear us out. We know this doesn’t have the best reputation. As far as food halls in the city go, this one is probably the most frowned upon. Over the years, it has fallen from its original concept. BUT! When we were researching on where to eat a lobster roll (a must-have when in New England – at least for these Maryland foodies) the BEST and top-ranking rolls were severely out of our budget for our quick layover in Boston. So that’s how we ended up in the tourist frenzy of Quincy Market.
We found Walrus & Carpenter Oyster Bar online which offered an affordable combo of the lobster roll and a bowl of clam chowder. Both of which were high on our list of things to try. The reviews were mostly positive so we plugged the coordinates into our GPS and off we went. Unbeknownst to us, the restaurant we had chosen was in the market. Not to be deterred, we saddled up to two empty stools and ordered what we set out to feast upon. The clams in the chowder were slightly chewy, but overall a decent bowl. The roll, however, was a hit! We deliberated over a hot buttered or a cold with mayo before finally deciding on the hot. Ultimately, we were happy with our decision to save a few dollars without sacrificing much taste.
If your pockets run deeper than ours, Row 34 was high on our list of desirable places to sample this staple of the northeast.
PW&A Hot Tip : If you’re sleeping on Southwest points, it’s not too late! We have the Southwest credit card and often accumulate enough points for city breaks like this one. Generally, we let the Southwest sales decide where we are going based on the cost of points to get there. It’s like travel roulette for the budget backpacker. Only these days, we’re mostly sans backpack.
Final Thoughts On How to Spend a Layover in Boston
There is probably no wrong way to spend a long layover in Boston, except for maybe settling into a boring seat without beer in the main terminal – beanless and sad. That would be a waste of an opportunity for adventure. We hope our itinerary inspires you to get out there and fill your bellies with the best that Boston has to offer. Did we miss one of your top eats? If so, let us know in the comments what we’ve got to try on our next visit to the city!
Cheers Friends,
Megan + Matt
