Adventures of a Wandering Thirtysomething

I’ll be the first to admit, I wasn’t expecting much from Boston for our 1 ½ day stopover en route to the Azores.

My thoughts of Boston have always been the same stereotypes: Dirty Boston accents. Bro town. Drinking lots of beer…or “beah”. The red-headed stepchild of New York or Philly. Kinda boring. Rude people.

None of these stereotypes was exactly incorrect, but what I did find was that I genuinely liked Boston. Its proximity to water, seafood-dominated food scene, and seemingly active lifestyle made me feel right at home. And its centuries-old architecture made me feel like I was in my favorite neighborhoods in New York without all the dirt, grit and general lack of livability that comes with New York.

Our first day was largely spent on a mission for great food. We dropped our bags at the perfectly located Renaissance Waterfront, where we had a huge comfy room complete with partial water view and easy access to public transit, and decided to take a long walk to Tremont Street to savor a lobster roll at B&G Oyster.

We staked out a spot on the patio and enjoyed the sunshine while taking our first bites of fresh oysters and one of the best (and most expensive) lobster rolls in town. Though the price was a bit steep, the roll was jam packed with lobster. One was enough for the two of us. Also impressive were B&G’s accoutrements of French fries, slaw and pickles. Usually an afterthought on the plate, each item was absolutely delicious.

After lunch, we wandered Tremont Street a bit more, popping our heads into a great gift shop where we snapped up some local treats like peppermint salt water taffy and rosemary truffle sea salt caramels. They even carried goat milk soap from Nashville’s Little Seed Farm.

Just a few hours later, we were eating again, this time at O Ya, a highly rated and award-winning sushi spot specializing in very creative and non-traditional twists on sushi. We ordered a little bit of everything from the menu including geoduck, squid ink soba and chicken skin sushi. Shockingly, the desserts were insanely good. Who knew a sushi restaurant would have an amazing pastry program?!

The next day, we started our day very early in Cambridge to scope out the Harvard campus. Although my IQ and SAT score would never pass muster there, it was cool none-the-less to walk on America’s first and oldest university campus amongst so much history and prestige. After a quick ice cream stop (hey, we were on vacation so ice cream at 11 am is totally reasonable), we made our way downtown for a walking tour of the historic district.

Having been to cities like Savannah where there’s so much American history starting in the Revolutionary War times, it was incredible to see sights that preceded that time and that were so important to the early foundations of America. Grave markers of Paul Revere, John Hancock and Sam Adams, the balcony where the Declaration of Independence was first read aloud, the book store where Hawthorne, Emerson and so many other literary minds gathered; it was all a treasure trove of history.

Needing a break from history and the heat (it got up to something like 90 degrees), we headed over to the Back Bay neighborhood for the other known lobster roll spot: Island Creek Oyster & Bar. Holy smokes. We would go back to Boston just to eat here again! Best fish sandwich we’ve ever had, hands down. The lobster roll, with generous use of Old Bay Seasoning (one of my faves) was awesome. And the oysters were incredible as well. Plus, they make their own in-house sodas. I tried a radicchio and pear soda, which was delicious and so unique. We’re still talking and dreaming about that meal!

Refueled, we headed on for a long walk through the Back Bay neighborhood where we strolled along block after block of beautiful row houses and cute boutiques, finally ending at the Boston Botanical Gardens where the tulips were fully in bloom.

With just a few hours left before our scheduled flight departure, we made a quick detour to check out our Loews Boston Hotel (so charming!) and made one last stop at the historical Omni Parker House. Yes, Omni is a competitor with Loews, but its long tenured history of hosting John Wilkes Booth (he shot Lincoln just a few days later), JFK (he asked Jackie to marry him there), and many other dignitaries, as well as employing  the likes of a young Malcolm X, and Ho Chi Minh,  make it a must-see. Plus, they not only invented the Parker House roll, they also are the creator of the Boston Cream Pie, which we just had to try. We didn’t expect much, but were shocked to taste a deliciously light and creamy dessert. It was seriously SO GOOD!

Satiated and exhausted after having walked 15 miles in a single day through the city – yes, that’s not a joke – we grabbed our bags and headed for the airport for a red eye flight to the Azores.

Boston: We’ll definitely be back!