A Perfect Date Night in Boston.

Claire here 👋. Some of you may know this already, but I am getting married this year and have been full-steam ahead on wedding and honeymoon planning (ICYW, our honeymoon will be in Japan..using all of Alyssa’s tips and tricks on traveling to Japanl!). So we decided it was time to blow off some of that steam! Last week, we took a night off from coordinating the romance to actually enjoy the romance for a night! It was so lovely, I wanted to share it with our club members.

Alyssa added this image to this blog post without Claire knowing… but isn’t this photo soooo cute?


Whenever we plan a date night around town, we stick to three rules: 

  1. We each pick two places for our Tour de Boston. 

  2. Public transportation is a must.

  3. We can only pick three things from the menu (to save stomach space for all the stops)

My fiance Kenny works in Fenway so we met up at our favorite patio in Boston: Taberna de Haro [link]. Last summer, we had the chance to travel to San Sebastian, Spain, and we’ve been chasing the pintxos high ever since. Their patio gets the loveliest breeze in the early evening, and drinking txakoli while snacking on gildas is about as darn close to the outdoor alleyways of San Sebastian’s Old Town as you’re going to get while watching decked-out Red Sox fans walk towards Fenway Park. 

The green line conveniently picks up right in front of Taberna, so we rode it into the city for Kenny’s pick: dumplings at Taiwan cafe [link]. It’s one of our favorite spots for dumplings, though you can’t go wrong with anything on the menu. Chinatown is just a short walk from the Commons, which is buzzing with Boston tourists on the Freedom Trail. We take the scenic route, meandering through Boston Commons and the Boston Public Gardens, enjoying golden hour on the pond and making pretend plans to do the Swan boats or Duck Tours on the next date night (though in all honesty, I’m just waiting for the next relative to visit me…Duck Tours are oh so much fun!)

At Taiwan Cafe, we carefully select one pan fried dumpling, one soup dumpling, and some garlicky pea shoots. Consistent in their execution and expediency, all three dishes hit the table in less than ten minutes and we dive in, trying not to burn our mouths from over-zealous excitement. Almost as quickly as the dishes arrived did they disappear; and we are left with just the splatters of black vinegar dipping sauce on the table and our shirts, content and full enough for the halftime show: Boston at Sunset over the Longfellow Bridge.

The MBTA gets a pretty bad rap - I’ve been known to rant from time to time - but the Red Line ride over the Longfellow Bridge makes up for every delayed train I’ve ever been burned by in my 15 years living here. Going over the bridge at dusk while the whole city is bathed in a golden light makes the work week fully melt away. We headed to Kendall, to our third stop: Row 34 [link].

We count a dozen oysters as “one dish” and round it out with the Fish and Chips and New England Clam Chowder (sometimes its fun to play tourist).  It was such a nice night that we walked from Kendall to Central Square to pick up the 86 bus for the fourth and final date night spot. 

For our last stop, Kenny surprised me with my favorite date night spot in Boston: The Koji Club [link]. I am certainly biased, but I absolutely adore our little bar for date night. And while it is always entertaining to watch dates unfold from the other side of the bar, it was oh so nice to be there on a date! Ordering from the menu, we sat at the bar and split the Caviar Service, diving deep into conversation about our honeymoon and all the things we were looking forward to the most about visiting Japan. It was the perfect end to our Tour de Boston date night, and a lovely reminder to slow down and enjoy the incredible eating and drinking establishments our city has to offer. 

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