It’s no secret that I have a love affair with Boston. From its cobblestone streets and brownstone buildings to its gardens and coffeeshops… it’s one of my most favorite places. In my early 20s, there were many occasions when I drove into the city alone to wander. Thankfully my husband shares an equal love for Boston and together we’ve spent many weekends meandering around the city… shopping, trying new restaurants, exploring parks. Now these days, a couple bags, a stroller, a car seat and a tiny human heavier, our trips look different. Just as exciting, but quite different.

The weather has been unusually warm for November and my adventurous soul has been wanting to take advantage of these beautiful days. Only problem is, my husband works all week which means Jackson and I fly solo. No big deal when we’re going for a hike or going to Trader Joe’s or heading to a local coffeeshop or park… all places I know well and feel comfortable with. Different story when the idea of going to Boston crossed my mind.

The parking alone can be overwhelming. And then what if I get lost walking around the streets. Or what if a gang of dirt bikers raced down the street and tried to steal my purse. What if Jackson wouldn’t eat the food I bought at a restaurant. What if Jackson screamed the entire car ride home in rush hour traffic. It’s wild how a child changes your entire perspective on things because all these thoughts and more went through my brain. Before Jackson came to be, I would have gone into the city without a care in the world. But these days, I have a baby to protect and keep happy and well fed and unpredictability is scary.

But the weather was supposed to be in the 60s (it’s November in Massachusetts, this never happens) and the foliage is still beautiful and the Public Garden and a hot coffee and a new bookstore on Charles Street were all calling my name. So while Jackson napped I sat with my journal and wrote about it. I reminded myself that life is too short and far too amazing to waste sitting at home on such a perfect day. I reminded myself that I’m most happy when I’m spontaneous and take adventures, even those that scare or intimidate me. And I promised myself that as soon as nap time was over, come hell or high water, we were going to Boston.

And you know what? We made it to Boston. And parking was a pain in the ass but we managed. And we didn’t get lost walking around (but if we did, thank God for phone GPS). And we didn’t see any gangs of dirt bikers (but if we did, I’d be damned if anyone was stealing my purse or hurting my baby). And Jackson didn’t want to eat the lunch I bought but he was perfectly happy eating a cookie and goldfish. And he screamed for some of the ride home but along with becoming a Mom I’ve also become Elastigirl and can reach my arm into the backseat and feed him while I drive (don’t lecture me on the safety of this). And everything worked out because it always does (especially when you don’t take things too seriously). And we had the best day.

We started with lunch and a cappuccino at Tatte.

Beacon Hill Books & Cafe was the most charming store I think I’ve ever encountered. It reminded me of a modern The Shop Around the Corner from You’ve Got Mail.