Some trips you plan for months. Some just land in your lap.
This one landed in Boston — and it was exactly right.
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Home Base: The Seaport Hotel
I stayed at The Seaport Hotel, and if you've never been, put it on the list.
The location alone justifies it. The Seaport District has transformed into one of the best neighborhoods in Boston — waterfront views, walkable, striking in the winter in its own way. The hotel sits right in the middle of it with harbor views that hit differently with the low December light coming off the water.
But the location is just the beginning. The staff there are genuinely warm — not the scripted-hospitality kind of warm, the actual kind. Every person I dealt with was friendly, attentive, and made the stay feel personal. The restaurant is excellent — not just "hotel restaurant good," actually good food, the kind where you find yourself not wanting to leave for dinner because the menu keeps pulling you back. The bar has the same energy, and the bartender I ended up chatting with was one of those people who makes a solo drink at a hotel bar feel like catching up with an old friend.
And then there are the amenities. I wasn't going to let the trip pass without taking full advantage of what they have: sauna, steam room, pool, fitness center. Started the morning right. The spa side of things was exactly what I needed to shake off the travel and warm back up before a full day in the city.
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The JFK Presidential Library
First stop of the day, before anything else: the John F. Kennedy Presidential Library and Museum.
It sits out on Columbia Point overlooking the harbor — a beautiful building in a setting that earns it. South Station is practically at the Seaport's doorstep, and the Red Line runs straight down to JFK/UMass from there. Easy, direct, worth every minute of the trip out.
This was my first presidential library, and it will not be my last. I am making it a goal to visit more of them. There is something about standing in a space built around a specific life, a specific era, a specific set of decisions — with the actual documents, photographs, and objects — that you cannot replicate reading about it. You leave understanding things differently than when you walked in.
I had a blast. I learned a lot. And on the way out I picked up a copy of Kennedy's own book — Profiles in Courage.
What is inside the library, I am going to leave for you to discover yourself. Go see it. That is the only recommendation I will make here.
What I will say: a summary and review of Profiles in Courage is coming to this blog soon. It is that kind of book — the kind you read and immediately want to talk about.
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The Long Walk: Seaport to Downtown
With the library done, I looped back to the Seaport and set out on foot for downtown.
That stretch, from the Seaport through the Fort Point Channel area and into downtown, is a good walk. Not a short one — a solid 20+ minutes in the December cold along the waterfront and through the streets — but the kind where you arrive somewhere feeling like you actually got there rather than just appeared.
The views coming across the Congress Street Bridge over the channel are worth it. The contrast between the modern Seaport on one side and the old downtown on the other — the Custom House tower, the old brickwork, the harbor in the background — is one of those Boston scenes that never gets old.
The cold is real. December in Boston is not a weather lie. But there's something about walking a city in the winter that makes you feel genuinely present in it. You're not scrolling. You're not distracted. You're just there, in the city, moving through it.
That walk — probably the best part of the day.
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Lunch at Union Oyster House
For lunch, there was only one right answer: Union Oyster House.
This is not a trendy spot. This is not a farm-to-table concept or a chef's latest project. Union Oyster House is the oldest continuously operating restaurant in the United States — open since 1826. Before it was a restaurant, the building itself had already lived a few lives: it was a dry goods store, and during the Revolutionary era it housed the printing press that published the Massachusetts Spy, one of the most influential newspapers of the Revolution. Daniel Webster used to drink brandy and eat oysters at the same bar that's still standing today, supposedly putting away a staggering number of oysters and brandy in a single sitting on a regular basis. John F. Kennedy had his regular booth (booth 18, still marked). The building itself is older than most countries.
You walk in and the history is tangible. Dark wood, low ceilings, the raw bar right at the front, the hum of a room that has been doing this for two centuries. I went with the clam chowder and the crab cake off the menu — both delicious, the chowder the real thing, not something approximating it, and the crab cake done right, not over-breaded or hiding what's actually in it. Sat with it long enough to appreciate that some things don't need to be reinvented.
If you're in Boston and you skip Union Oyster House because you think you're above a tourist spot, you're wrong. Go. Eat the chowder. Get the crab cake. Sit at the bar if you can.
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Quincy Market and Faneuil Hall: History, Crowds, and Gift Shopping
After lunch I walked over to Quincy Market and Faneuil Hall, which are right next door to each other and together form one of Boston's most iconic (and reliably fun) destinations.
Faneuil Hall has been at the center of Boston civic life since 1742. It was the site where Samuel Adams and other patriots gave speeches that helped ignite the American Revolution — it earned the nickname "the Cradle of Liberty" long before that phrase was printed on anything for tourists to buy. The hall itself still operates as a public meeting place and marketplace on the ground floor. Standing in it, you feel the weight of what happened here.
Quincy Market is the long granite marketplace building adjacent to Faneuil Hall, built in 1826 (the same year Union Oyster House opened — good year for Boston institutions). The market hall runs about 500 feet long and is packed with food vendors, shops, and the kind of energy that comes from a place that's been a gathering point for the city for two centuries. Tourists and locals alike — it works for both.
I was on a mission: gifts for the family. Faneuil Hall and Quincy Market are genuinely good for this — there's a mix of local vendors, specialty shops, and things you can't find anywhere else. Came away with gifts I was actually happy about, which is the best you can say for shopping anywhere.
And of course — clam chowder. You don't walk through Quincy Market without getting a cup of clam chowder from one of the vendors. This is non-negotiable. The stuff they serve there is thick, proper, and served in a bread bowl if you want it. "Clam chowdah" — in Boston, that's not an accent, that's a religion.
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The Walk to the MFA
After Faneuil Hall I started making my way toward the Museum of Fine Arts — the last stop of the day. It's a real distance from downtown, so I walked as far as Back Bay and let the T handle the rest.
Boston rewards walking, at least for a while. The streets in the older parts of the city don't follow a grid — they follow cow paths and colonial-era logic, which means every block reveals something unexpected. You turn a corner and there's a 300-year-old cemetery. You cross a bridge and the whole harbor opens up. The low December light sharpens everything — the air, the cold, the sound of your footsteps on the old brick sidewalks.
I took my time getting through downtown and into Back Bay, then hopped the Green Line for the last stretch out to the museum. Sometimes you don't need to walk the whole way to feel like you got there.
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The Uber Home: A Hawaiian Right at Home
The museum was the last thing on the list — and by the time I came out, it had started snowing. Snuck up on me while I was inside. I called a car back to the Seaport rather than push my luck on foot in it.
Caught this one of Back Bay, near the Common, on the ride back — the snow just starting to stick.
The driver that pulled up was from Hawaii.
Hawaii. Driving an EV through Boston's famously chaotic layout, in December cold — now snowing — that he said was nothing at all like home, with the calm of someone who'd long since made peace with the city's traffic patterns anyway.
We talked the whole ride. He'd been in Boston for a while and still missed the trade winds and the warmth, but said the EV's heated seats got him through a New England winter just fine. He was great company. The car was silent and warm, a nice break from the snow outside.
Best Uber ride I've had in years.
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On Taking a Trip to a City You Like
There's no secret formula to a good trip, but I've landed on one approach that keeps working: go somewhere you actually want to be, eat something that's worth the calories, walk until you find something that surprises you, and talk to at least one stranger who makes you glad you left the house.
Boston checked every single one.
Good hotel. Good food. Good history. One Hawaiian driver, one warm EV in the December cold, and a city that's been doing its thing since before the United States existed.
That's a good trip.
— Dr. Scott