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Pro Tips for a Family Trip to Boston

Disclosure: This post was sponsored by Walmart and Russell;all opinions are my own. For more Dadletic adventures follow the hashtag #dadlete. 


When I say we took a family trip to Boston, it is technically true. My wife, the kids and I were all in Boston for a few days. But while I was exploring the city and visiting friends, she was mostly stuck in a convention hall working. Though this definitely sucked for her, it was also kind of a pain in the ass for me. As every dadlete knows, parenting is a team sport. I rely on my partner when I’m not at my best or my kids are doing their worst. My wife and I tag team, divide and conquer, back each other up, give each other breaks and breathers, and generally do whatever it takes to parent the hell out of our crazy insane adorable children. I’m a stay at home dad, so I’m used to going it solo. Just not generally for 10 hours straight, in a new city, without television or electronics easily available in case of emergency. We definitely did some things right on this trip and I have a few Pro Tips to share. Game on.

As soon as we checked into the hotel, Allie and I grabbed every pamphlet and flier about things to do in Boston that the lobby offered. Then we all went to the Children’s Museum and, while the kids had a fantastic time on the indoor (vaguely educational) playgrounds, Team Grownup made a plan for the next day.

The next day, we completely nixed that plan.

Like Russell FreshForce Perfomance Underwear, which wicks moisture away from your body and lets cool air in, dadletes know it’s important to go with the flow.

Pro Tip 1: The Best Way to See Boston is Not by Duck

At the concierge’s advice, I took the kids the Old Town Trolley Tour instead of the more obviously kid-appealing Duck Tour. (Dadletes know it’s a good idea to take the advice of experts…except when it comes to directions in which case I know EXACTLY where we are right now.) The price tag for both excursions was pretty similar, but while the Duck Tour takes a finite 80 minutes (60 on land and 20 in the water), the trolley offered hop-on/hop-off service all day long. There are 16 optional stops and we hopped on at number 10, about a block from our hotel, at 9:30 a.m. and didn’t return until around 5:30 p.m.. You read that right. I used the tour to stay busy for the entire day! Keeping children entertained, while trying to get the most out of a historic city like Boston, isn’t a sprint. It’s a marathon.

If it were just my wife and I, I would have loved to explore some of the historic and artistic neighborhoods where the trolley stopped. Penny might have even had some patience for that; Simon not so much. He whined any time he had to take more than 10 steps in a row. So, we bypassed those destinations, as well as Fenway Park because we were attending a conference event there later that evening. We only made three stops on our journey, but had a fun and educational time at each. First, we got off at Cambridge and took a short train ride to Harvard. We went to the COOP to get a feel for the college life (and take a quick pee break), after which we chilled in Harvard Yard, rubbed John Harvard’s foot, and visited the Museum of Natural History.

Pro Tip 2: Go to Museums for FREE

Most parents have a membership at a kids museum or zoo and this dadlete is no different. Flashing my Liberty Science Center card got us into the  Museum of Natural History, Children’s Museum and Boston Museum of Science absolutely free. BOOM! The trolley ticket also came with a Boston Harbor cruise that didn’t have to be used the day of the tour, but that we were, unfortunately, unable to use after because of inclement weather and the high probability of my kids whining the whole time.

Pro Tip 3: Coupons are Everywhere

The trolley ticket also came with coupon for Boston Tea Party Museum, which we made our second stop. For young kids up to middle schoolers, this is a must hit museum. After learning about and participating in an interactive recreation of the Tea Party, the museum itself offers a few surprises of its own including SPOILER ALERT seemingly magic paintings of Benjamin Franklin and King George that debate the merits of “taxation without representation” and a free and independent colony, taken from real letters between the two. There is also a captivating short movie about the “shot heard round the world.”

Pro Tip 4: Don’t be Embarrassed to be a Tourist

Finally, we got off at Faneuil Hall because it’s pretty much against the law not to when you’re visiting Boston. I promised the kids ice cream because VACATION and BRIBERY! We went to the aptly named Cookie Monstah truck, where there are no cones, only baked from scratch cookies. No one seemed to mind. We enjoyed the sights, sounds and smells of Quincy Market, along with the various street performances, before rushing back to the trolley stop to make sure we didn’t miss the last trolley of the day. It was a fun, full, and exhausting day that gave us a glimpse of an awesome city.

Pro Tip 5: Wear Comfy Undies

It was a hot day and, despite the trolley breaks, we did a ton of walking. Like I said earlier, entertaining children while exploring an entire city is a marathon. And no marathoner or dadlete wants to chafe. I wore my Russell Freshforce Perfomance Underwear and was cool as a cucumber. I mean my cucumber was cool as a…you know what, let’s move on.

Pro Tip 6: Chill Til the Next Episode

The next day we visited a friend and spent all day at his pool. If you have a friend with a pool, I highly recommend calling him and imposing.

Bonus Tip:

On a rainy day, when you’re museumed out, go to Kings Bowling. There aren’t many lanes, but each one has retractable bumpers so everyone can have a good time. The menu is not the normal chicken fingers and french fries bowling alley fare; they have craft beer and an interesting food selection. I got the Fat Elvis burger, which comes topped with fried bananas, a spicy Tai peanut sauce and bacon. Dadletes have to refuel after a super fun marathon day with the kids exploring Boston. This was a tasty way to do it.


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  1. Cool write up man! When I go to Boston, I’ll follow your tips, I’ve been thinking of subscribing to those expensive undies that they send to you by mail. So I got that one covered. 😀

    • admin admin

      Thanks! I kind of want to overhall my entire underwear drawer. The Russell’s are definitely an upgrade over what I have. I’m curious about some of those other (more expensive) brands, too.

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