A Romantic Weekend in Boston – What Could Possibly Go Wrong?

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Romantic Weekend in Boston



It all started perfectly, as we checked into a lovely and romantic Boston boutique hotel (The Kimpton Nine Zero), opened a bottle of red wine, nibbled on some fruit and chocolate and admired our 19th floor picture-perfect view of the city. I carefully took the time to arrange my romantic weekend away outfits in the closet for a rare three night stay. The planets had aligned for an event that happens only once every few years. – my parents took the kids. What could possibly go wrong? There were no stuffies to look for under the bed or temperatures to check. Just two adults, on a fancy free weekend away in a fabulous city that neither of us had visited before.


Kimpton Nine Zero Boston


I spend a lot of my time planning family trips in great detail to make them as enjoyable and stress-free as possible. When it came to this weekend away with my husband, I wanted to do very little planning. I wanted to be spontaneous. I booked the flights and the hotel, and that was about it. As my husband is quite passionate about food experiences, I let him have full control over our Boston dining. Little did I know, however, that this is where our weekend visions diverged. In retrospect, I realize that although I wanted to be completely laid back, I did have some expectations around how the weekend was going to go.

For example, my perfect morning in Boston, would start with breakfast in a stylish café, where I would enjoy a latté or perhaps two, while reading the whole newspaper (not just the headlines, while rushing my coffee as I often do with kids). My husband’s perfect morning in Boston, involved a walk across town in the rain, to a tiny restaurant (4 seats – a dozen people standing outside), that promised Boston’s Best Breakfast Sandwich. The sandwich was agreeably fantastic, but the atmosphere was a little uninspired, shall we say. Due to this lack of seating, and the rain, we ended up sitting at a bus stop eating our breakfast – nary a cappuccino or newspaper in sight. Not wanting to seem high maintenance, I bit my tongue and vowed to offer more clarity for the following morning.


We had a great afternoon exploring the city by foot, trying out Boston’s Best Lobster Roll, Boston’s Best Cannoli, Boston’s Best Pizza Slice (you get the idea), from food carts or restaurants also lacking much visual charm. I was totally fine with this, however, as apparently this aligned with my expectations around lunch. Besides, I didn’t want to disappoint my husband who had diligently mapped out all these locations on a little piece of paper he had tucked in his front pocket.


Best Lobster Boston


Offering even less direction around dinner, I was fine with my husband’s suggestion of a Brazilian restaurant (apparently Boston has a large Brazilian community). I began my get ready time with an extra long shower (much longer than I can enjoy at home without running out of hot water), blow dryed and flat ironed my hair, took time to get my makeup perfect, and put on some ridiculously high shoes that had taken up way too much space in my carry-on bag to be at all sensible.

My first clue that my husband and I were once again misaligned was the plastic cafeteria style tables.Then it was the plastic coated menu and the caipirinha served in an acrylic cup. I was also clearly way overdressed. The food was great, of course, but once again, the ambiance was lacking. Fortunately, as would be typical for such a place, we were in and out in about 40 minutes.

I had a flashback at this moment, to a kid-free weekend getaway to Portland a few years back. I recall sulking in a cafe (that served Portland’s Best Coffee), while my husband waited in line at Voodoo Doughnut for an hour. This was clearly not the first time we had experienced this problem. I had simply blocked it from my memory.

What to do in such a situation? This was not the evening that I had imagined, and it needed to be salvaged (nothing that an extra glass of wine couldn’t fix). We popped next door to a Sports Bar (with me still looking way overdressed), watched a great baseball game with a lively bunch of locals, and even managed to enjoy Boston’s Best Ice Cream Sundae on our Uber ride back to the hotel.



By our second day in Boston, my husband and I were on the same page. The sun was shining and we grabbed a couple of bikes from the Kimpton to enjoy the city. First stop, a cute cafe with chairs. It was a perfect day with our expectations apparently aligned. Our evening was equally enjoyable – kicked off by fancy craft cocktails at a little place in the North End (Ward 8). This was followed by a lovely dinner at a quaint, traditional Italian restaurant (Nico’s) that had something that I now realized was important to me – tablecloths.


Ward 8 Boston


My observations about the weekend, which all-in-all was fantastic, was that our little pitfalls were entirely due to a lack of communication. After 15 years of marriage, I still think my wonderful husband is going to turn into a magical mind reader. One of the keys to a successful trip, with or without kids, is that expectations and reality align. Talk to each other !

I highly recommend Boston for a romantic weekend away. Just look how much fun we had (see our 1 minute video) !



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