If there has been one American city I’ve wanted to visit over the years, it’s Boston. Especially when I’ve been told over and over how pretty a city it is (architecture), its walkability and of course the good food and drinks!

So, it was time to make a trip to see Boston a reality. When a seat sale presented itself, I coordinated the weekend with family & friends (who live 1 hour outside of the city) and we booked it!

Me and my Mom flew Air Canada via Toronto to Boston – which was pretty painless and easy, although with the time change, it was an all day affair. The Boston airport is relatively simple so we arrived, and you can be literally 10 min. to a part of Boston or 45 min. depending on traffic. We were the latter ;).

Night 1:

We enjoyed dinner in the North End at a quaint little Italian joint called Massimino’s Cucina Italiana Restaurant. The staff are characters, there’s no fuss and the pasta was delicious. Some house made, some not, but fresh ingredients, a decent wine list, and unbeatable ambiance. At our table we enjoyed the special homemade pasta with rose cream sauce, scallops and prawns; Linguine with local clams in light white wine and garlic sauce; and Limoncello as our dessert! There was a nice selection of wines, I chose a Barbera d’Alba (although not the perfect match for what we ordered, we didn’t care 😉 which was a wine to suit everyones palate.

Massimino’s

From here we walked a few blocks of the North End to where the busier streets were, full of quaint eateries, bars, pubs and pastry stops. All around us were brown stones and old English style architecture of homes and apartments. And of course we had to stop for a Cannoli at the legendary Mike’s Pastry that is big enough for 4 people (I’m being serious)! This cash only spot has four lines inside and out the door, but it goes fast as its cash only. Choose from nutty pistachio to oreo chocolate, with more traditional flavours in between. We opted for a traditional chocolate cream one. Delicious but HUGE!

Canoli!

Day 1:

We began the day at Cafeteria on Newbury Street for brunch, a chic street to walk the day away, eat and shop. The menu was simple with a bright atmosphere and nice staff.

From here we walked to the Skywalk for a birds eye view of the city and to get our barring. They offer complimentary voice tours via walky talkies (definitely worth doing). Great views and a great way to understand how the city is laid out!

view from the Skywalk

Then we walked to the famed Boston Common (oldest city park in America) and took in the autumn colors, the city ambiance of locals enjoying their city and of course the Ducklings. A true story of a family of ducklings who held up traffic on Charles St. years ago, and everyone fell in love with them so created bronzed statues of the family within the park, aptly named “Make way for the Ducklings”. This is also where you can start to walk the Freedom Trail. So we set out to stroll the city by way of the trail, passing the Massachusetts State House, The Park Street Church, Granary Burying Ground (where Samuel Adams is buried) to Faneuil Hall. Where we stopped for lunch. A fantastic indoor/outdoor “market” of sorts full of shops, places to eat and drink.

This is where I enjoyed my first Lobster Roll at Boston & Maine Fish Co.! It was yummy. and a very ‘local’ thing to do. We also had some freshly shucked oysters and Clam Chowder (with beer of course ;). We took in buskers singing and the whole atmosphere of this marketplace. So much fun.

fresh seafood at Faneuil Hall

Night 2:

From here we walked to the harbour and as it chilled down for the day, and we began to fade, we landed ourselves at the Boston Sail Loft Restaurant/Bar (a local favourite) for an afternoon snack and drink. We caught the low hanging moon over the water before returning to our hotel by taxi.

 

a few pictures from the day

Our dinner was later and close to the hotel at The Salty Pig. Fantastic, casual atmosphere with delicious pizzas, pastas and more. We shared a charcuterie board, some wine (I had the 2015 Mas de Libian Vin de Pétanque) ( chilled ) and I enjoyed the Fettucine Nero made with wild boar ragu. Great menu here, the food was great!

charcuterie & cheese board at The Salty Pig

Day 2:

As if Day 1 wasn’t enough!!! We made this day a bit simpler. We walked over to the Mapparium found at the Mary Baker Eddy Library. Fantastic for families and all ages. You stand inside a stained glass map of the world at 1935. Lots has changed since then, so its fun to discuss quietly what you see. The acoustics are amazing, so the slightest whisper can be heard by everyone in the room (or globe) – so don’t talk about the tour guide out loud (even if she was in a walking coma)! Highly recommend a visit here.

The Barking Crab

From here, we checked out of our hotel, and drove the car to The Barking Crab at the opening of the Fort Point Channel along the water. What a spot! We had a long, enjoyable lunch with live music and fresh seafood, and local Oktoberfest beer.

At our table there was local long neck clams, lobster and fried clam rolls, roasted lobster, fish & chips and Shipyard Pumpkinhead Ale with a cinnamon spiced rim. All the food was delicious and the staff fantastic!! And because our afternoon lunch went so long we missed out on the Boston Tea Party Ships & Museum which was just across the water (next time!).

Day 3:

We began our day with a visit to “lake country” about an hour outside Boston in Sturbridge, to see the colors of autumn. Then back to Boston for lunch and we had to make time to enjoy an Irish Pub, so we checked out The Black Rose at Faneuil Hall. Nothing like Shepard’s Pie, Reuben Spring Rolls, Guinness Beef Stew, Curry and Chips and Boston Cream Pie to top it off with a beer of course!

Bahston – you are ‘Wicked Pissa’ (local talk for super cool) – thanks for a great weekend!