Connor’s Boston 10th Birthday Trip {Pt. 1}

Several years ago, a bit of a miracle happened: I heard about a fun family tradition, and it wasn’t too late to implement it! 

See, I always jump onto the bandwagon late for things. You know those cute little monthly photos of babies wearing little stickers with their monthly age on them? And those first-day-of-school photos with the kids holding cute little chalkboards with their age, what they want to be when they grow up, teachers name, etc.? Yeah, by the time I saw those ideas, my kids were well past the age where it made sense to start doing that. 

But one day a few years ago, I was talking to my friend Amy about her daughter’s upcoming 10th birthday and she said that she and her husband were going to take her — and just her — to New York for the weekend. David was also 9 at the time, and I became totally hooked on the idea. Dave and I don’t get to spend a ton of time just him, me and one of the kids, so the thought of having a whole weekend with just the birthday boy was amazing. 

So we implemented the idea with David when he turned 10 in May of 2015, and he chose to go to New York as well. I never did a full post about it, but I did mention it in this post. Thanks to a sorority sister who is a TV producer in New York who knew someone who knew someone, we ended up getting a tour of the set of Chopped and got to go on set and actually sit at the judge’s table.It was kind of amazeballs.

The only problem was that, when Connor decided that he wanted to do Boston for his 10th birthday trip, I realized that we set the bar WAY high with D. How on Earth was I going to live up to that? Spoiler alert: I did. And possibly surpassed it. But we’ll get to that in a bit. 

I started off planning to do everything in one post, but it was getting insanely long, so I decided to break it up into two different posts. This post is going to cover how we got there, where we stayed, where we went, what we loved, and how we scored some crazy amazing experiences — so that if you’re planning a trip to Boston with kids, you can hopefully get some good ideas. I will cover where we ate {pretty much our favorite part of any trip we take} in another post. If you have any questions or want more information about anything I talk about here, please don’t hesitate to ask in the comments section or reach out via email

How We Got There & Where We Stayed

For several reasons, but mainly because it would have been an almost 8-hour drive for us, we decided to take Amtrak partway. We left early on Wednesday morning and drove to Stamford, CT, where we caught the train to Boston. Connor was super excited, as it was his first real train ride, and I can’t tell you how easy and convenient it was.

We pretty much stay at Marriotts whenever possible when we travel, so for this trip, we chose the Boston Marriott Copley Place, which is about a block and a half from the Back Bay Amtrak station, so we didn’t have to worry about taking an Uber or a cab.

The hotel was fabulous, and I would stay there again in a heartbeat. As I said, it was very close to the Back Bay train station, and it was walking distance to the shopping on Boylston and Newberry Streets, Boston Common, and Boston Public Garden, as well as the start of the Freedom Trail {more on that later!}.

Boston Marriott Copley Place

The best part, however, was that when we got to the hotel, we discovered that the staff had upgraded us to a suite {full disclosure: Dave is a Lifetime Platinum Elite member of Marriott Rewards, so we often get upgraded} and had left wrapped gifts for Connor in the room. Dave had just emailed the hotel before we got there and let them know that we were there celebrating Connor’s birthday, and they took it upon themselves to get him a LEGO set and a book, as well as leave a handwritten note. Connor was beside himself. 

Marriott Boston Copley Place

What We Did

Freedom Trail
Our first full day in Boston, we decided to walk the Freedom Trail, which is a 2.5-mile long route through the city that takes you to 16 sites that played a part in the American Revolution.

All three of us thought it was fascinating to see so many places that we had heard of in history class — like the Old South Meeting House, the site of the Boston Massacre, the Old North Church and Bunker Hill. Connor is really into history, so I think he was especially excited. 

There are lots of tours available, but we prefer to do things at our own pace, so we chose to walk it ourselves. I would definitely recommend that, if you choose to forgo a tour, you either download the Freedom Trail App or purchase a book.

While there are informational signs at each site, the book and app both go into more detail about what exactly happened at the site and included information about a few unofficial stops as well. You can purchase books at the Visitor’s Center in Boston Common for around $10-$15. 

I think one of the coolest things that happened on the Freedom Trail was at the Massachusetts State House. We decided to once again skip a formal tour and just wander around ourselves, so we eventually wandered into the House Chamber, where we were asked to remain in the back, behind a velvet rope. Dave started chatting with a guard and happened to mention we were there for Connor’s birthday, and all of a sudden, the guard looked at Connor and said, “Come with me, I have a birthday present for you.” He not only allowed us through the rope, but he allowed Connor to get up on the dais, handed him the official gavel, and allowed him to bang it on the podium. I thought my man’s head was going to explode.

A few pointers about the Freedom Trail: first, it is LONG. Between the trail itself and all the other walking around we did, we actually walked over 8 miles that day. If you are traveling with small kids or anyone who has trouble walking, you might want to consider splitting it up into a couple of days or trying out one of the bus tours that are available. Even if you’re not, you might still want to consider taking a break at some point. We stopped and had a bowl of chowder {sorry, chowdah!!} at Union Oyster House {more on that in the next post}, which was a nice little pit stop.

Second, be prepared for it to be busy and hot. We were there at the end of August, so a lot of schools were already back in session, but I imagine during the summer it can get a tad crazy. 

Third, keep in mind that, while the majority of the spots along the trail are free, some do have an admission fee, while others have a suggested donation. 

Boston Public Garden
One of my favorite places that we went was Boston Public Garden. I could have stayed there all day. It was the first public botanical garden in the country, and it is one of the most beautiful places I’ve ever been in a city. 

In addition to the amazing number of trees, plants and flowers, there is a large lagoon where you can take a ride on one of the Swan Boats, which have been operated by the same family since 1877. 

Another fun part of Boston Public Garden is the Good Will Hunting bench, which Dave was particularly excited about. We walked around and I’m pretty sure we looked at every single bench in that whole damn park {and trust me, there is no shortage of benches} before we found it. And as we did, we had a couple from England come up to us and ask if we wanted to swap pictures — apparently it’s become somewhat of a landmark. {Please excuse the really weird pose I’m doing in this photo — I think I was shifting to try to get more comfortable right when he took the picture. As a result, I just look like super odd and uncomfortable.}

New England Aquarium Whale Watch
Holy moly me, was this amazing. Even though I was super, borderline-crazy-person excited, I was also a bit nervous to do a whale watch trip. It’s about a 4-hour trip, you’re obviously not guaranteed to actually see any whales, Connor is prone to motion sickness, and I also have a tendency to get a little dizzy and nauseous in situations like this. I had visions of Connor and I puking off the boat the whole time while we drove around in Deadliest Catch-style seas. 

I should not have worried. 

First, Connor and I both popped a Dramamine before we went, and we were totally fine. Neither Connor nor I ever felt even the slightest bit nauseous, and the waves weren’t bad at all. {The sea was not rough that day, my friends.} 

And we saw a boatload of whales {see what I did there??}. 

The trip we took was through Boston Harbor Cruises, but it was run by the New England Aquarium. During the trip, crew members came around and explained where we were going, why that area is good for whale watching and what to look for. Once we got out to the feeding grounds and started seeing whales, they told us a ton of information about the individual whales, many of whom they have named and could recognize from various markings on their tails and bodies. 

It was amazing. I think we saw a total of around 10-12 whales, many of which were within several yards of the boat {I purposely didn’t crop out the boat railing in this next photo so you can clearly see how close they were}.

We chose just the whale watch, which costs $53 for adults and $33 for children ages 3-11 {children 2 and under are $16}, but there are combo tickets available that also include tickets to the aquarium itself which saves you about $7 per ticket.

A few pointers about the whale watch: first, the boat is pretty big, but they do pack a lot of people on it. The ideal place to be is outside on the upper deck, as you can easily move from one side of the boat to the other, depending on where the whales are, but there is only room up there for about 20 people or so. I would recommend getting to the dock pretty early {at least a half hour before the time on your ticket} in order to be toward the front of the line and have your choice of seats. 

Second, it is windy and COLD, especially if you end up sitting outside {although there are lots of areas where you can sit inside, too — and there’s a snack bar! Yay, snacks!}. You can expect it to be at least 15-20 degrees colder than in the city, so definitely bring a sweatshirt and/or jacket, even if you go in the summer. 

Third, keep in mind that you are going out into the open ocean, so even on a relatively calm day like we had, the water will be choppy. If you are at all prone to motion- and/or seasickness, I highly recommend wearing Sea-Bands taking some type of motion sickness preventative medicine. 

Fenway Park
As cool as the whale watch was, the highlight of our trip — BY FAR — was the Red Sox game.

We all love baseball and we’ve been trying to go to as many stadiums as we can, so we knew without a doubt that we’d be going to a game in Boston. Because, I mean: FENWAY. The Green Monster. Connor was super excited to go, not just because it was a new stadium for him, but one of his favorite movies is Field of Dreams. He kept saying he hoped he’d hear someone whispering “Go the distance!” and look up and see “Archibald ‘Moonlight’ Graham” on the scoreboard.

But what he didn’t know was what we got to do when we got to the stadium. 

A couple of weeks before the trip, I had emailed the Red Sox {I just went to their website and found the email addresses for a couple of their community relations people} explaining that we were coming to a game to celebrate Connor’s 10th birthday, and asking, in addition to doing a scoreboard message, was there anything else we could do while we were there. I didn’t have extremely high hopes, but I figured it didn’t hurt to ask.

I got a call back two days later from someone in the front office asking if we’d be interested in doing a private tour of the stadium and going onto the field for batting practice before the game. 


I thought Connor’s head was going to explode when we found out what we were doing {we surprised him when we got to the stadium}, although I think Dave and I might have been just as excited. We were met outside by an intern named Samantha who handed Connor a gift bag full of Red Sox swag and we were then taken on a tour of the entire park. We went into the press box, we saw a garden on the roof where they grow herbs for the various concession stands, we saw where the visiting team enters the stadium {down a tunnel that also houses the garbage dumpsters — hilarious}, we got to go in an area of the stadium usually reserved for season-ticket holders where they house some amazing memorabilia. 

We also got to go on the field for batting practice. Unfortunately, the Red Sox got in extremely late the night before, so they didn’t do batting practice, but we got to see the Orioles bat and watch Manny Machado hit 4 or 5 balls completely out of the stadium. It was pretty damn cool. 

When the tour was done, and we got to go to our seats, Connor sat there for a minute and then looked at me and said, “This has absolutely been the best day of my entire life.” 

Mom and Dad FTW.

I guess the moral of all of this story is: don’t be afraid to ask. Samantha said that they love doing tours like this for people and wish more people would ask about it. I half expected not to hear anything in response to my email, and honestly wouldn’t have been shocked if I did hear back and they said there wasn’t anything else they could do. This went so far above and beyond our expectations, I can’t even explain it.

Freedom Trail Information
Freedom Trail Tours
Boston Public Garden
New England Aquarium Whale Watch
New England Aquarium
Fenway Park
Red Sox Tickets
Fenway Park Scoreboard Messages

Hopefully these suggestions will give you a little guidance if you’re planning a trip to Boston anytime soon. If you have any other suggestions of things we didn’t get to do this trip, I’d love to hear them, so drop them in the comments below! 

Stay tuned for Part 2: Where We Ate, coming soon!

Disclosure of Material Connection: Some of the links in the post above may be affiliate links. Among others, we are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to Amazon.com and affiliated sites. This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”

You Might Also Like