Boston had been on my bucket list for years. So when my husband, Ted, got invited to speak at Harvard right around my 50th birthday, I knew I had to join him.
We only had two days, but that turned out to be exactly enough: one full day to explore the city of Boston, and one more to wander Harvard’s campus and watch Ted give a phenomenal talk to a room full of leaders. By the end of it, I understood why people LOVE this city – and why, especially this year, it deserves a spot on your bucket list.
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Day One: Wandering Boston
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I flew in, dropped my bags at the hotel, and hopped in an Uber straight into the city. I started my adventure in Beacon Hill, the most beautiful and historic neighborhood in Boston. The homes are 200 years old and absolutely breathtaking. I giggled with delight at every block.
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I even stumbled upon the bar that inspired Cheers. Naturally, I had to walk in. Nobody knew my name, so I kept walking.
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From there, I strolled through the first public garden in the United States, then The Boston Common, which was established in 1634 and became the first public park. It was here that I bought a ticket for the Freedom Trail. You can absolutely walk the trail on your own for free, but I love a good story, so I splurged () on the narrated tour. Our guide walked us through Boston – explaining how different sites shaped American history. Every guide tells different facts and stories, and every group asks unique questions, so you could do this tour over and over, and never have the same experience twice. I LOVED the tour and look forward to doing it again.
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Another option for exploring Boston is the hop-on, hop-off trolley that drives around the city, narrating important facts and stories.
After the tour, I purchased an obligatory cannoli at the North End of town. There’s a big competition about which bakery makes the best one. I tried Modern Bakery, next time I’ll get one from Mike’s to determine who makes the better pastry. They are almost across the street from one another, so you can try them both and decide for yourself.
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Next, I walked to the site of the Boston Tea Party, where I stopped at the gift shop for an ornament. Later, I ducked into a restaurant that once served the very signers of our Constitution. Sitting there, I was nearly in tears thinking about how those same floors once held the people who built this country.
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Exhausted and happy, I caught an Uber back to the hotel, and ended having dinner with Ted.
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Day Two: Harvard, Birthday Lobster Rolls, and JFK’s Table
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I woke up on my 50th birthday to avocado toast and Coconut Coffee at the Phin Coffee House (SO GOOD).
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Next, I rented a Bluebike – there are pick up and drop off spots around town – rent a bike for the FULL day or the minutes add up FAST. (Don’t ask me how I know) Exploring Harvard’s campus on bike was an adventure and a delight. The turns are sharp and the brick sidewalks are historic, beautiful, and BUMPY! I was in AWE of the gorgeous architecture, stately churches, and centuries of history packed into a few square blocks. Knowing I was walking the same steps as Thomas Jefferson, JFK, and John Adams gave me chills. I stopped at the bridge to watch the rowers practice and wandered out to the football field just to take it all in.
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Later that day, I got to sit in the audience and watch my husband give a phenomenal talk to a room full of leaders, one of those proud-spouse moments I won’t forget.
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That night, we headed back into Boston for dinner at the bar inside one of the city’s most storied hotels; the kind of place where presidents and historical figures have stayed for generations. I ordered a fabulous lobster roll and a cup of clam chowder, which I’m convinced are the two non-negotiable things you must eat in Boston.
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After dinner, the host took us to the very table where Jackie and JFK got engaged.
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Why You Should Go – Especially This Year
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I cannot recommend a trip to Boston enough. It’s a city where you can stand in a garden, a tavern, a church, a print shop, or Paul Revere’s home, and feel the weight of the people who gathered there to build a nation.
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This year, there’s an extra reason to go: 2026 marks 250 years since America’s founding, and Boston is throwing a celebration to match.
Every year since 1776, the Declaration of Independence has been read aloud from the balcony of the Old State House. During the Bicentennial in 1976, Queen Elizabeth II stood on that very balcony for the reading, exactly 200 years after Bostonians tossed British tea into the harbor. In a nod to history, and a good sense of humor, Boston even reimbursed the Queen for the long-lost tea.
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If you’ve ever thought about visiting Boston, this is the year to do it. Walk the Freedom Trail. Eat the lobster roll. Stand where history happened. I spent my 50th birthday there and walked away with a deeper love for this country and the people who built it, and I can’t think of a better way to celebrate 250 years.
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If you’ve been to Boston, leave a comment and tell me what you love about this city.
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Click here to read my Travel Guide for Minnesota’s North Shore
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