Road Trip: Massachusetts

Neither Alina nor I had visited Boston (pronounced: BAH-STAN) previously so we were eager to check it out and see what it had to offer. Finding affordable accommodation downtown is next to impossible on a modest budget. After lots of inquiries we finally secured an AirBnB room (with private bathroom) in the suburb of Watertown. We figured 4 nights would be just enough to see the sights but also to get a feel if this was somewhere we’d want to live.

But first we had to make our way from Vermont and find a hotel for the night along the route. While on the road we secured a last minute deal at the Fairfield Inn near the town of Sudbury which turned out to be a great choice. Not only was the hotel itself great, but it is located in a picture perfect neighborhood with tree-lined streets and impressively landscaped gardens.


Rockstar parking…


Tip: Consider using for finding cheaper hotel rates. Occasionally, it can offer much cheaper rates than,, etc.


As Sudbury is just 45 minutes away, we arrived into Boston before noon. We decided to check out Harvard University which incidentally is in the city of Cambridge – what Bostonian’s commonly refer to as ‘across the river’. The River Charles divides both cities as it makes its way to Boston Harbor.

We ditched the car and set off on foot to explore Harvard, MIT and everything in the middle. Despite having the ‘free’ breakfast buffet earlier in the morning it was impossible to resist the lure of eating ‘real’ eggs and pancakes at the Mass Ave Diner. We appreciated the reasonable student pricing so much so that we returned the following day too!


Being the weekend before Labor Day, the Harvard campus was buzzing with new students parading around in orientation groups and moving into nearby dorms. It was worth the visit if only to watch the super excited and proud parents walking around 10 feet tall and taking photos of everything on campus like crime-scene photographers.

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Let’s not forget MIT…



We checked into our Watertown AirBnB late in the evening and were given a warm welcome by our hosts Drew and Lisa who occupy the entire second floor of the building along with the huge deck. It’s a nice little neighborhood with good public bus links to both Harvard Square (to connect with the metro line) and downtown Boston. We learned that just 5 blocks from their home was the location where the Boston Marathon bomber was apprehended back in April, 2013 after a huge police operation.



We relied on public transportation for the majority of our stay and had no problems getting into and around town. It’s clean, safe, reliable and you can look up routes and schedules using Google Maps.


The rechargeable CharlieCard allows you to pay your fare at a discount without the need to carry cash.

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Free Walking Tour

Taking a walking tour is one of the best ways to orientate yourself in a big city but also to get some local knowledge before setting out to explore alone. Fortunately Boston is very much a walking city with few hills and changes in elevation.

Not only is Boston a big city, but it is also very rich in history despite being less than 400 years old. To that end, we signed up for two separate walking tours: Freedom Trail and North End/Little Italy.

Freedom Trail

The Freedom Trail is named for the 2.5 mile red-lined route that runs through the city marking 16 important historical sites. All of them are significant to the American Revolutionary War and independence from Great Britain. Of course one can freely walk this trail unguided but we chose the highly rated Free Tours by Foot and were glad we did.

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Our guide Brian was full of enthusiasm as well as knowledge; perhaps the best tour guide we encountered on our travels thus far. We learned that the letter ‘R’ is unwelcome in these parts and its use is totally FAHNED upon.

As you can see the weather was perfect…

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North End

The North End is on the tourist trail but it still feels like an authentic Italian neighborhood despite the obvious gentrification that is underway. Our tour guide took us around many of the famous historical sites but also took time out to point out and recommend some local businesses (okay, let’s be real: bakeries, cafes & pizza joints!) which we visited afterward. More on that later.


Faneuil Hall with Sam Adams brewding (!) outside…


In addition to being a nice building the Quincy Market has every food stall you could imagine: the quintessential tourist trap perhaps but there’s probably some great food to be had if you choose wisely.



The statue honoring Paul Revere. Most know him for the famous ‘Midnight Ride’ to warn of the British invasion in 1775 but there are many other interesting facts about him too.

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The interior of Old North Church where lanterns were lit in the steeple to indicate whether the British were going to invade by sea or by land. The militia were laying in wait for the the British when they finally arrived in Lexington and so began the American Revolutionary War.


Copp’s Hill Burial Ground with Old North Church in the background…

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Holocaust Memorial

We passed by the New England Holocaust Memorial as part of the walking tour but decided to come back afterwards to read more of the inscriptions. There are six glass towers each etched with numbers representing the tattoos assigned to victims at the camps. The number six is significant in that it represents the 6 main concentration camps, the 6 million murdered and the six years of war.

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Red Sox

Fenway Park is one of baseball’s most iconic parks and is home to the Boston Red Sox. With the team struggling in the standings, we had no problems securing a couple of bleacher seats for a game against the New York Yankees. While the game did not live up the billing, it was great to explore an old, albeit re-developed, cathedral of American sports.

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Boston Public Library

This is a stunning public library and is mostly definitely worth putting your head in the door for a quick look. You can find some temporary exhibits on the second floor in addition to a small cafe.


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Top of the Hub

The Top of the Hub is a restaurant located on the 52nd floor of the Prudential Building offering a 360 degree view of Boston. It’s the place to come all dressed up and reservations should be made in advance. Unfortunately we did neither and settled for a drink at the bar: water with lemon & hold the disdain please!

Charles Street Jail

The historic Charles Street Jail, located in Beacon Hill, was renovated and converted into the Liberty Hotel back in 2007. It is a listed building of national significance and thus retains much of the original architecture and materials. It’s very much an upscale hotel today but don’t let that put you off from having a drink in the lobby or listening to some free live music like we did. In fact the band, Hot Sauce, gave us a CD to take with us on our road trip.



Where to Eat

Polcari’s Coffee

Polcari’s is the best coffee in town by many accounts. The owner was super friendly and even offered to take take pictures of us behind the counter and tell us some stories about his Italian neighborhood. He then pointed us to the only location where we could taste his coffee as he didn’t have a license to sell drip coffee himself!

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So off we went to Prince Postale where we had another chat about the neighborhood, drank some of Polcari’s coffee and learned where to find the best slice of pizza. The guys here were divided on the pizza question so we were duty-bound to try both of their recommendations.

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First, we devoured the tasty pizza square at Parziales Bakery and then we headed around the corner to Monica’s Mercato which was just as good, but different!

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Maria’s Pastry

The tiny Maria’s Pastry shop is a wise choice for tiramisu but especially a cannoli: the filling is added AFTER you make your selection so you can actually taste it at room temperature. Think about that the next time you have a frozen cheesecake at the Cheesecake Factory!

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Mike’s Pastry

There is a much bigger selection of pastries to choose from at Mike’s Pastry so it’s unlikely you will leave empty handed.


Sam La Grassa’s

Oftentimes the highest rated places fail to deliver but fortunately Sam La Grassa’s didn’t disappoint. It was encouraging to see the place packed with locals on their lunch break. Of course it helps to have a pay check when the cheapest sandwich runs close to $14.

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Cape Cod

The Cape is a few hours south of Boston and is a popular summer destination for tourists, celebrities and wealthy families alike. We arrived just as high season was ending and therefore had the benefit of cheaper accommodation and less crowded beaches.

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Again we turned to AirBnB and we were rewarded with a perfect 4 night stay in the small town of Hyannis. Our hosts Mitchell and Kera provided us with bicycles to ride down to the nearby Craigville beach and also a permit for the more restricted Dowses beach. There are so many visitors that many beaches restrict parking entirely to permit holders.

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For two days while the sun shined we enjoyed the beaches…

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And when it rained we took a trip to Provincetown to see the town but also to visit the Cape Cod National Seashore and eat our way back home!

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In the town of Orleans, we stopped by Sunbird Bakery & Café for a very tasty breakfast sandwich…

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Ice-cream was enjoyed at the Hot Chocolate Sparrow which Alina assures me was very good…

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We didn’t spend too much time in this seaside town due to a torrential downpour but we did take time to eat at Chatham Fish ‘n Chips. Quelle surprise!

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The fish was likely brought ashore at this Chatham pier (or Costco!)…

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Cape Cod Brewery

A small brewery with just 20 full-time staff, tours are provided Monday to Saturday at 11am. They only distribute within a 6 mile radius so it will be some time before they are acquired and destroyed by Anheuser-Busch InBev or Heineken.

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Boston is a terrific city: wonderful architecture & history, good public transportation, big sports teams, lots of great restaurants and for 8 months of the year some great weather. With Cape Cod and indeed the rest of New England nearby, it certainly surpassed our expectations and somewhere we’d have no hesitation in returning to.

Next Up

Our college tour circuit continues with a trip to Brown and Yale!

  • Michelle Garcia

    Have a friend from college living in Sudbury & she loves it . . .
    Funny you wrote “water with lemon & hold the disdain please!” about the Bahstan Prudential Building : )

    • Kieran

      It’s a nice place for sure and great proximity to Boston or even the mountains for skiing.

    • It’s a nice place for sure and great proximity to Boston or even the mountains for skiing. Thanks for reading in depth and not just being mesmerized by pictures 😉