Which U.S city is beautiful yet modest, rooted in history while keeping up with the times, seafood-filled and totally walkable?

BOSTON.

Ryan and I recently visited for a four-day weekend. It was my first time there, and his first time as an adult. We absolutely loved it and would go back without a doubt. Ryan happily used his IATA card to get us a discounted Fairmont rate (like, a 70% discount) so we were able to spend two nights at Copley Plaza Fairmont and one night at Battery Wharf Fairmont. We flew to Boston from Ottawa (on points, of course) and that was painless, as was the free bus and the $2.50 subway from the airport to our hotel. The subway system is great; very efficient, and the people are really pretty friendly everywhere.

In our three and a half days there, we leisurely strolled through most of the major neighborhoods in central Boston, including Beacon Hill, Back Bay, Waterfront, North End (Italian), Chinatown, Faneuil Hall Marketplace as well as venturing to Cambridge (Harvard). We literally covered almost the entire greater Boston area – mostly on foot, although a few times we used the subway one-way (i.e. in the pouring rain, and en route to Harvard – though it turns out the walk was only just over an hour from downtown to the Campus, which we found out on the scenic stroll back).

The city is structurally beautiful and without many high-rises, which is a change from Toronto, New York or Vancouver. There are also ample green space and beautiful parks, which really makes the city exude a more peaceful and less frenetic energy and pace of life. There were definitely upscale areas with fancy store-fronts and an older, classic feel (e.g. brick-lined sidewalks, gas lamps, and historic buildings) and then there were the areas that felt more like South Granville in Vancouver (urban and concrete). The Faneuil Hall marketplace was a fun place to be as was the waterfront.

The food in Boston was great! Pictured below is the best calamari we have ever had, from “Barking Crab” – alongside deep fried oysters. The batter was so crunchy, but not oily, and the seafood was textured and flavoured like it had literally just come out of the ocean – SO tender. Without a doubt, we decided unanimously that this was the most tender calamari we’d ever had (and we have probably had over 50 different calamari dishes). While I can’t compare the deep fried oysters to anything else because I’ve only ever had them fresh, BBQ’d or in a burger, I really couldn’t imagine them being any more tender or tasty. We both liked the calamari more, probably just because we have a deep love for this dish (as you may have already guessed from our glutinous and mounting 50+ count …). It was lightly seasoned and garnished with little flakes of what looked like parsley, a hint of garlic, grilled lemon wedge, and banana peppers alongside. If you are in Boston, check this place out – it’s casual, very kid friendly, and open-air dining on a dock. We also went to several other patios and one or two dive-bars while we were there, and were all around happy with the service and the food quality (not to mention the price – pints for $3 and two mains for $15! You’d be hard pressed to find that in Canada’s major cities, that’s for sure). There was also a place called the Rattlesnake near Copley Square that had a funky rooftop patio I’d happily go back to.

Further outside of the central core, we really enjoyed touring the Harvard campus and being able to take in some of the history that makes this city so interesting. While you could easily “do Boston” in 2 full days, it would be “go go go” and there would be very little time for patio-sitting or sun-basking (or siesta naps, haha) so I quite enjoyed our 3.5 days. It’s also a place you could easily take kids as it’s not as sprawling as New York (i.e. not as much walking required) and there is an Aquarium as well as the beautiful Boston Common garden. We didn’t make it to a baseball game, but that would also be a fun activity with kids.

In summary — Boston is a breath of fresh air. It’s walkable, beautiful, historical, and not that far away from us Canadians living on the East Coast!

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