Some of our trips are planned months in advance (Nashville, Vancouver, Las Vegas, New York City, Jamaica), other mere days. Our recent on-a-whim trip to Boston, Massachusetts fits in the latter category…and we had a blast! Here are the highlights.

Porter Airlines

  • I’m going to save some of the details for now, as I have my fingers crossed that I will get the opportunity to partner with Porter in the future to bring you a whole bunch more information about how great it is to fly with them, but for now I will just say…it’s great to fly with them. When we were mulling over destinations my parents suggested we look for somewhere that Porter flies, based on their positive experience, and I’m glad we listened. We’ve only ever flown out of Pearson before and using the Billy Bishop Airport on the island was vastly different. More on Porter at a later date, I hope!

Boston Children’s Museum

I’ve been searching my memory going through the many other museums we’ve visited with the kids over the years, and I truly think this one takes the cake. My husband and I were blown away by the quality and my girls (ages 11 and 8) spent hours exploring. Some things we loved:

  • A huge range of hands-on, interactive and kinesthetic experiences
  • Lots of posted information, including tips for parents
  • A great variety for all ages, from toddler through tween
  • Familiar characters and themes (hello, Arthur’s city!)
  • Science, social studies (I thought the “Black Boston” exhibit was fascinating), language, mathematics and the arts all incorporated
  • Spacious and clean with friendly, helpful staff

I loved this “welcome to kindergarten” classroom replica!

Boston Tea Party Ships and Museum

Tickets for this attraction are free with the purchase of the Old Town Trolley Tours Hop-On-Hop-Off Passes during fall and winter, and discounted during spring and summer. I will admit, history is not my passion (my brother knows more than enough historical information for the both of us), but this was a really fun way to learn about the events of the Boston Tea Party, including the lead-up and the aftermath, through a multimedia experience. Visitors are drawn into the story (you’re even given a card with your character’s name, though there’s no pressure to do anything other than take it all in) and have the chance to throw some “tea” off the ship. I’m glad we didn’t miss this one.

Old Town Trolley Tours

In every city I visit I try to take advantage of hop-on-hop-off offerings (and even ensure that I book a hotel near one of the stops), and Old Town Trolley Tours in Boston definitely met our needs. Most places we visited were on the route, and staying on for an entire loop gave us a great overview of the city. Plus, the drivers were very informative and entertaining, sharing tidbits that I never would have known otherwise. As a lover of all things celebrity, of course I wanted to see the restaurant where JFK proposed to Jackie, the original “Cheers” exterior, and one of the buildings that was used in the film The Departed. Recognize it?

In spring and summer your ticket includes a free Boston Harbour Cruise; in the off-season you get a second consecutive day free to ride the trolley.

Hilton Boston Back Bay

We got a great deal on our room though the Berklee Performance Center website, as we were seeing a show at Berklee the first night we arrived. It had everything we needed in a hotel, including a spacious corner room, a pool and hot tub, and we even splurged on their room service one night! We also spent our snowed-in afternoon (more on that later) playing cards in the Starbucks lounge.

Natalie MacMaster and Donnell Leahy in Concert

This was probably the highlight of the trip for my daughters, who got to see their friends from home performing on stage (fiddling, stepdancing and singing), and also got to play on the tour bus and enjoy dinner in the green room! Music is such an important part of our everyday lives, and it was great to give the kids this experience while travelling as well.

While I recommend you see this talented family if you get a chance, my broader tip would be that you should look into any concerts or shows that might be taking place in your destination city. You never know what you might find!

Mike’s Pastry

Based on several social media recommendations, we got off the trolley at stop 2 and took a short stroll through Little Italy to the famed pastry shop…and weren’t disappointed! Note that it’s cash only, and the very long lines do move quickly.

Cathedral of the Holy Cross

As I captioned my social media post, everyone goes straight from the airport to Mass…with their luggage. Right? Yes, there was a church we could have attended right beside our hotel, but someone insisted on checking out the cathedral. Personally, I fell in love with the stained glass above the altar, and also got a photo of the window of St. Cecilia, patron saint of musicians.

A post shared by Kate Winn (@katethismomloves) on Mar 13, 2017 at 5:50pm PDT


  • Harry O’s: Right across from the Cathedral, we purchased our first meal in Boston from this little pizza place, with delicious food (I had a fantastic calzone made right in front of me, the girls’ slices were huge, and they even have great dessert), and friendly, top-notch service.
  • Thornton’s: We love our breakfast diners, and Thornton’s was our choice for two of the mornings of our trip. The menu is huge (they serve lunch and dinner as well), and I had the eggs/toast/hashbrowns meal one morning, and Nutella crepes the next – great-tasting and reasonably priced. There’s no separate kids’ menu, but tons of options that worked for my girls, including smaller items like muffins and bagels with cream cheese. 
  • Ned Devine’s Irish Pub in Quincy Market (trolley stop 1). Coming from the city in Canada with the largest Irish population to the US equivalent, of course we had to check out an Irish pub! This one was just what you’d expect: comfort food (I had the fish and chips), Irish tunes playing over the speakers, and of course Irish beer on tap. With a kids’ menu and a convenient location, I’d recommend this spot for sure (and coincidentally, two ladies from Ireland who were riding the trolley with us also chose it for lunch!)
  • Cheesecake Factory: Yes, yes, it’s a chain, but we don’t have it in Canada and we’ve never been before. The filet mignon was incredible (and bigger than I’m used to being served at a restaurant), and of course we each got a slice of cheesecake to go from their extensive selection (since we were so full from our meals there’s no way we could eat it there!) With choices like Reese Peanut Butter Cup, Oreo, Smore and Turtles it was difficult to decide….good thing we were all willing to share!
The Blizzard
Well, that’s the end of my list of recommendations…significantly shorter than a usual trip, but there’s an explanation for that. I had planned two jam-packed days of sightseeing…and on the second day, a blizzard was expected and the entire city shut down! No school (not that we were affected by that, but we get lots of snow at home and schools are never closed), no hop-on-hop-off, and absolutely no tourist attractions that were open. It was an adventure for us, and we actually enjoyed a day of downtime at the pool, playing cards, watching TV, helping my 11-year-old set up a blog that I may or may not let her share with others someday, and starting my notes for this post!
But because we missed half of the attractions I had planned to visit, I also want to share with you a list of places that are now on my must-see list for my next trip to Boston, most of which had offered us admission that we weren’t able to take them up on!

One caveat for Canadian friends travelling to the US: be very mindful of the exchange rate. When you convert prices in your head (or on your phone!) it makes you more careful when shopping or making choices about other expenditures.

Now, if you’re planning to visit Boston and have any questions, please feel free to ask! Also, if you’ve visited in the past (or are a local) and have other recommendations that I’ve missed, I’d love for you to add your thoughts!
Back to planning my next travel adventure…

Disclosure: We were provided free admission to some attractions. Opinions are, as always, my own.

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