36 hours in Boston

Read all about our 36 hour trip to beautiful Boston, MA.

Boston, a city full of charming people, rich history, winding trails and mouth-watering dishes. Boston is a city full of little surprises waiting to be discovered. When you compare cities like New York or Chicago, Boston is in a category of its own. With some buildings dating back to the 1600’s, this city is living proof that its rich heritage is still very much alive.

From the 36 hours we stepped foot into Boston, our minds were filled with history and our bellies full of delicious cannolis and hearty dishes.


As we had settled in after our flight, we wasted no time in venturing out. We first wandered over to Beacon Hill, since our choice of stay was at Omni Park Hotel, this neighbourhood was just a 5-minute walk over. We wandered through cobblestone streets, strolled down beautiful alleyways and stood in awe at every beautifully-decorated windowsill in the neighbourhood.

We were a bit hungry from the flight, so our first stop for food was at Tatte Bakery. Serving up meringues the size of your head and rosebuds filled with freshly piped chocolate, this was the perfect sugar rush we needed to get back on our feet.

We found the one street we were purposely looking for – the infamous, Acorn Street. This one street leading uphill has the perfect setting for a picture under the American Flag.

After my photo op, we both felt that a visit to Cheers was the perfect drink to officially welcome ourselves to Boston.  We wandered over to the original Cheers location and ordered ourselves a beer and if you’re thinking, did anyone know our names? No, nobody knew our names.



After our pints, it was off to Boston Common where we wandered through the park, stared at statues and took in the beautiful city skyline. After a few photos and taking our time walking through the park, we decided to head back to our hotel to dress for dinner.

Dinner was at Sweet Cheeks Q. This BBQ joint serves up some serious lip-smacking bbq with your choice of meat, one hot side and one cold side. I went for the tender beef brisket, coleslaw and macaroni and cheese. If you end up going, make sure you start with their warm biscuits and housemade maple butter. You will not stop at one – trust me on this.

The next day, we decided to do what typical first-time visitors do and explore the Freedom Trail. We started at Boston Common and worked our way through the State House, Kings Chapel and Burying Ground. We wandered our way up following the trail to the Faneuil Hall and Quincy Market. I imagined Faneuil Hall would have been larger but in fact, it’s neighbour Quincy Market was quite large and impressive. Here, your choices of food and portion sizes were endless. Lobster rolls, clam chowder, falafels, pizzas and giant baked goodies were all ready for our hungry stomachs. After touring the halls, we got back on track and made our way to Boston’s North End.

North End is a beautiful neighbourhood with a lot of character. Here, Little Italy is located right in the middle of this neighbourhood. We stopped in for Boston’s best cannoli at Mike’s Pastries – this did not disappoint. A fresh cannoli sprinkled with chocolate chips was the speciality. Of course, if you’re not a cannoli fan, their chocolate eclairs and giant cookies were all ready for us as a backup.  As you can imagine, we dove right in without waisting any time.


To work off all those cannolis, we wandered over to Paul Revere’s House and gazed in. Unfortunately, a lot of these historic marks ask for payment and can be pricy at times to wander through, so we stood outside and poked our heads through the gate. We then weaved in and out of Little Italy and realized we needed to get back on the Freedom Trail to continue our journey.

Our last stop on the trail was Copp’s Hill Burying Ground. You can still see the bullet grooves on some of the graves from the Revolutionary War. This was truly a magnificent cemetery full of history. We noticed so many young girls and boys who had lost their lives before and even during the war that were buried here.


After all that walking – we worked up a serious appetite. We decided to head over to the Harbour Walk for some real authentic Boston seafood. Boston Sail Loft and Café was recommended by a friend and it was a great place to stop for lunch. This charming little restaurant sitting on top of the water served up Clam “Chowdah” in a classic mug with Oyster crackers. The soup was thick, creamy, and delicious. Definitely a filling choice. And to wash it all down? A Boston lager from a local brew pub, of course.


After lunch, we wandered around, passing Ripley’s Aquarium and other tourist hotspots. We somehow wandered into the  Financial District where we stood in awe of the architecture of some of these buildings. There was so much history around us – it felt like we needed to read every plaque on every building. We found it interesting when the buildings were first erected and what they were built for.

Our feet were in serious need of a break, so we ducked into an Irish Pub just down the road from our hotel where we enjoyed an ice cold beer and listened to a local band playing in the corner. After our beers, we both felt a little nap was in order to get us ready for Boston’s nightlife.

The restaurant we planned on going to for dinner was called Bostonia Public House. This restaurant served up pub food with a twist. Options such as hot or cold lobster rolls, lobster mac and cheese and fresh oysters were the main favourites. Of course, we tried all three!

After dinner, we wandered through the streets of Boston. Walking down different roads and on the main area for big shops and brand names. We then came across a neat little outdoor skating rink and watched as people from all ages skated around. We contemplated renting skates and taking a turn for ourselves but we both agreed the day of walking literally exhausted our legs. We took our time wandering back to the hotel where we seriously crashed.

Since we only had the morning to wander before our flight back to Toronto, we decided to pop into the cutest bakery that was only steps away from the hotel. Sweet Bakery was this charming little cupcake shop that served up delicious and uniquely flavoured cupcakes with cappuccinos and espressos. We tried the macaron cupcake and the blueberry buttermilk pancake cupcake (try saying that 5 times fast). The decor of this place matched the charm of the cupcakes. Pink tufted benches and marble tables lined this bakery.


We both agreed the bakery was sweet but we needed an actual breakfast, so we wandered around the corner to Paul and had a little taste of Paris before we left.

As we made our way back to the airport with our luggage in hand, we both knew we would be returning to this historic city. The people, history and food are what made our stay so enjoyable. With the time we had, we were impressed with the amount of ground we covered. Of course, we will make our return in the summer so we can see Cambridge and Cape Cod.


Where we stayed:

Omni Parker Hotel

Where we ate:

Sweet Cheeks – serves up BBQ

Bostonia Public House – pub fare

Boston Sail Loft Cafe & Bar – great for classic clam chowder and a few of the water

Tatte Bakery – Cafe and dessert

Sweet Cupcakes – Cupcake bakery with pink tufted chairs and marble countertops

Mike’s Pastries – Best cannoli in Little Italy

Paul – French pastries

Cheers – The original is in Beacon Hill

Where to wander:

Acorn Street – Famous street and shot you can’t miss

Map of the Freedom Trail

Harvard University – We didn’t get to visit Cambridge, but we plan on coming back for a day spent here

Blackbird Doughnuts – This cafe serves up the most uniquely flavoured doughnuts


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1 Comment

  • Reply
    Sharon Sloan
    March 18, 2017 at 8:34 am

    Having visited Boston already, it was as though we re-visited with the writer. We loved the Boston drawl. So upper-crust, you know!!

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