I learned a lot about Boston in 24 hours. First and foremost, wear comfortable shoes as you are going to walk everywhere. Even with their lovely mass transit system, you will still walk. So think practically with your footwear. Secondly, if you are a Yankees fan, keep it to yourself. Giants and Jets are fine…no matter. But something about Yankees fans. Third, if you’re friendly, you won’t find a stranger in Boston. It’s a northern city, but no where near as rushed and formal as New York City. It’s a place that a southern bred kid could possibly call home.

It’s also overflowing with history. Every turn puts you face to face with a monument, a story and more. Our next step in our historically driven wandering was to the Charlestown Navy Yard via the ferry to see the USS Constitution. It’s the world’s oldest commissioned warship afloat and please note the specificity of that title, haha.

Another great part of Boston is that most tours are free and so was the tour for the USS Constitution. Our lovely guide was a US Navy seamen named Judy and she did an excellent job describing the daily life of a USS Constitution sailor as well as a fantastic recounting of the story that inspired the ship’s nickname of “Old Ironsides.”

Imagine sleeping here with over two hundred other men.

The Freedom Trail was again the deciding factor following our tour of the ship. We followed the red line deeper into Charlestown, past Winthrop Square and up to the Bunker Hill Monument.

In front of the granite obelisk sits a statue of William Prescott, an American colonel in the Revolutionary War. If you’ve ever heard the infamous phrase “Do not fire until you see the whites of their eyes” then you’ve heard of Prescott.

To get the full experience of Bunker Hill, you need to climb the 294 steps within the obelisk. You’ll be sweaty and out of breathe and you’ll wonder what prompted such a ridiculous expenditure of energy…but it’s worth it. Well, maybe not. The view was okay. Think of it as a bonding experience for your group. We had to take a little break after the climb in an attempt to stop sweating.

From the Charlestown area, we headed back to the North End and eventually into Chinatown. Getting lunch proved a little more dramatic than expected but we found a good place to stop at Dumpling Cafe. Better yet, NPR just did a story about dumplings so you can learn more here. I ordered fried pork dumplings and a simple vegetable noodle bowl. Jessica got something amazing delivered in a bamboo container…I think they’re called Xiao Long Bao or Steamed Soup Dumplings. Jessica for the win.

We ran into a rusty and rowdy group on the way to the Samuel Adams Brewery.

Our tour guide’s name was Louis and he’s one of the funniest and most knowledgeable tour guides ever. No lie. If you visit the brewery, ask for him.

After the tour, we took a trolley over to Doyle’s Cafe. Established in 1882 and near the brewery, it was the first place that the Samuel Adams Boston Lager was put on tap. It’s also been the location for scenes for Mystic River, Boston Public, and more. But please note the that this is a “party” trolley complete with poles, disco ball and a fist-pumping driver that will make you believe “fist pumping” can be awesome.

It was here that we had an incredible lunch. Jessica and I split an order of a lobster roll and a reuben. Let me just say, there’s a bit of culinary magic happening at Doyle’s.

On the way back from the brewery fun, we came across a building identified as the location of Bikes Not Bombs. We had seen their stickers around town and while I’m still investigating them, their mission to use bicycles as a vehicles for social change sounds awesome.

And now for another piece of American culture and history: Fenway Park, the oldest Major League Baseball stadium currently in use. Enough said.

Alright…not really. Did I mention they have fried dough? Basically it’s a funnel cake but just a large piece rather than “funneled” and still covered in powdered sugar. This is why I’m a runner…to keep ahead of the vacation calories I consume.

It was a showdown of the Sox between Chicago and Boston. We had bleacher seats courtesy of Steven’s aunt (a magical lady) and we cheered with the best of the rowdy Red Sox fans. Good times.