We’re officially not-newlyweds. Isn’t it crazy how fast a year can fly by? Time has moved quickly since university for me but this year feels like it went quicker than ever before. The anniversary really snuck up on us – we kept putting off booking an anniversary trip until we realized we were just a few weeks out and should probably get our act together! I’ll share more about our roadtrip in the coming days & weeks, but let me tell you about part 1 now.
Boston. A city I never really had an inkling to visit, but Mike knew it’d be a good stopover on the way to Cape Cod, where we planned to spend our anniversary. We packed up the Rover and took the surprisingly-beautiful drive on a Thursday, giving us a full two days in Boston that we managed to pack full of pretty much everything.
Our Boston To-Do List:
Walk the Freedom Trail + sightsee along the way / Eat Parker House Rolls / Drinks at Beacon Hill Cheer’s / Dinner at Union Oyster House / A Visit To Harvard [to live out my wildest Elle Woods dreams] / Jays vs. Red Sox at Fenway Park / Stroll through Back Bay / Dinner in the North End / Explore Boston Common + visit the ducks!
We stayed at the Omni Parker House and had a bit of a shock when we walked into a tiny!!! room that Mike had booked thinking a “full” was, you know, a large bed. Instead of a bed for ants. A mention of our anniversary weekend and we were quickly moved to a suite and they even sent along their original-recipe Boston Cream Pies and some bubbly. The hotel was in the perfect location and it was so easy for us to walk or take the T to anywhere we needed to go. Recommend!
It was conveniently also right across the street from Boston’s gorgeous Old City Hall – perfect for political nerds like us!
I’d crowdsourced some must-dos for the weekend and I’m happy to say that we knocked most of them off our list! We had dinner at Ristorante Lucia in the North End on our first night – try the Ammazzafame pasta – but decided not to get in line for Mike’s Cannoli.
After a few wrong turns in the North End, we managed to find Paul Revere’s house and Mike gave me a bit of a history lesson. We realized pretty quickly how walkable the city was and how easy it could be to find all the historic spots. It’s really too bad Toronto doesn’t have something similar!
We set out to walk the Freedom Trail on Friday, starting right outside our hotel at Old City Hall.
The trail took us to the graves of Paul Revere, Sam Adams, Mother Goose + Ben Franklin’s parents where everyone tosses pennies on the graves. Apparently there’s no *real* reason to do this – it’s a case of monkey see, monkey do.
Following the trail, we found Boston Common and immediately fell in love with it. It was kind of magical to find such a beautiful green space in the middle of Boston. Plus…the ducks! The duck pond was a nice surprise for me – especially when we found a nesting swan!
Beacon Hill – another must-see for anyone visiting Boston – borders the Common and is also home to the bar that inspired Cheers. Our meal there was surprisingly delicious: Mike had his first clam chowder of the trip and we split an order of (delicious!) onion rings. He grabbed the burger while I was lured in by the pretzel bun on the Coach’s Club Sandwich. If you’re deciding between the rings or the fries…definitely go with the rings. To. Die. For.
Not ones to stray from a political opportunity, we took the T to the JFK Presidential Library & Museum to bask in some Americana. Oh, we loved it. From Jackie O’s dresses to the campaign materials, we couldn’t get enough. You can also see his prized sailboat outside.
One cool nugget from our visit: we saw a seating chat from one of Jackie’s state dinners and found it so interesting that she would seat herself at an entirely different table from the President.
Friday night saw us having dinner at Union Oyster House, the oldest restaurant in America. I had the broiled scallops and still dream about them. They were buttery, crispy, flavourful…everything you hope for when you’re dining a stone’s throw from the Harbour. Such a great recommendation from my cousin-to-be (in 2018!), Tayler!
After dinner, we headed next door to the Bell in Hand Tavern, billed as America’s Oldest Tavern. Sensing a trend here? We sat at the bar and watched the Jays take down the Red Sox…and were luckily surrounded by other Canadians! They were celebrating a bachelor party and of course, my husband, life of the party that he is, joined right on in. Let’s say it was a late night with many blurry stops.
Our most jam-packed day was Saturday. We got a bit of a late start due to the previous evening’s hijinks, but we still managed to get it all done! Our first top was Harvard, the centre of my Elle Woods dream. Alas, I didn’t quite get that 175 on my LSAT (I wasn’t as far off as you’d think, though….).
The next time we’re in Boston – and there will be a next time – I’d love to spend more time exploring Cambridge. From what we saw, it was such a beautiful city. And Mom – I went to Harvard! Just like you’d always dreamed 😉
Post-Harvard, we hopped back on the T and headed out to Fenway Park for the Jays vs. Sox game. Mike’s splurge for this trip was a pair of seats right behind home plate. I’m not one to comment on ball parks, but the experience of a stadium like Fenway was something else.
We walked back to our hotel through the Back Bay area and it took even longer than anticipated since I kept stopping to take photos. It’s such a fun, Yorkville-esque area and I’d love to spend more time there next time as well…if only for the shopping and the epic Ben + Jerry’s location!
So that’s it! Our weekend in a nutshell! We absolutely loved Boston and can’t wait to go back soon. The city is so walkable and beautiful and we know that we only skimmed the surface of things to see & do there. I’d love to hear your suggestions for our follow-up visit in the comments! xo
PS. Next up in this series is a peek at the Cape Cod / Martha’s Vineyard leg of our trip. Stay tuned!