Road Tripping with 2 under 3

My mother thought we were nuts. Maybe we were. Regardless, we committed to the plan. We were in. For those who are new to our family we probably should provide a bit of context. Here is the background.

My husband and I both have a passion for sports. We met in the sports industry and stumbled upon our love for travel as we realized how much fun scheduling travel around sports can be. We connected over this. Bonded over this. Fell in love over this. The goal when we had kids was to keep this going. To enjoy this life of chasing last minute game tickets and exploring new cities with a new stadium as an excuse to get out of routine and explore. There are the go-to cities. The cities we go to over and over again because we either love the team, justify the proximity to home, love the city or all of the above. Boston is a great example of this.

Spoiler alert. We usually fly to Boston. We’ve done the drive a few times pre-kids but have always found it to be a really quick down and back trip so flying makes the most sense. We also end up in Boston a lot while visiting relatives out east in Canada so we sometimes do the drive from there. Love the city, love the people and love their stadiums (Fenway in particular). Their teams: NOT SO MUCH.

So last week comes along. Casual post-bedtime glass of wine and catch up with the hubs and he says, “what do you think about driving to Boston for Easter weekend”. I knew where he was going with this. Our beloved Maple Leafs are in a first round playoff battle with the Bruins and I knew game 5 was on Good Friday. My response: “Why don’t we fly?”.

Flights were going to be a lot. A lot a lot. Points weren’t an option unless we wanted to get hosed. We hummed and hawed. Do we bring the kids? Do we go for the whole weekend? Is it a down and back 24 hour trip? I’m not sure how but we landed on a plan. Leave really early Friday morning (4am approximately) and drive to Boston. Start the trip home Saturday and take our time, return on Sunday in time for family Easter dinner.

Duties were distributed. Darryl bought tickets to the game and booked our hotel. I booked a babysitter through an agency called “The Babysitting Company” for the Friday night game, packed all of the kids stuff and my stuff. I prepared for the road trip by packing every “favourite” toy I could think of, every snack known to man and a quick rest stop diaper pack to use in eventuality of disasters. I also switched out Harrison’s car seat to a toddler carseat (Clek Foonf). I couldn’t fathom putting him in the bucket for that long. He’s been pushing it in terms of size for a while now and I wanted him to be comfortable if we were going to have any chance at a painless 9 hour drive.

Thursday night we were out late at my stepsister’s birthday party but when that alarm went off at 4 we jumped out of bed. Loaded everything last minute in the car and then grabbed the boys and slipped them (in pjs) into the car. By the end of the street they were back asleep and shortly there after I was too (whoops!).

Around 7am we stopped for breakfast. Kids were holding it together. We made it to Boston around 3pm as we stopped a few times to stretch our legs and visit Target (my not-so-subtle obsession).

Our room at the Westin Copley Square was lovely. They have recently upgraded their hotel and completely refreshed the interiors. I loved the layout we had. Pretty large room and great couch that could be flipped towards the wall to make a toddler bed for George. Harrison’s crib was up to our room mere moments after we requested it. Overall this hotel “gets it”. We have stayed there multiple times over the years and with the upgrades I really don’t think I would want to stay anywhere else. Great club lounge with extensive breakfast options and wonderful staff.

One slightly funny side note was that a comicon festival was in town and the lobby and elevators were filled with festival goers in full fantasy costumes. Made for some interesting conversations with George but we got a laugh out of it.

Claire from The Babysitters Club arrived on time and was fantastic with the kids. She kept us updated and George raved about her the next day.

The TD Garden (where the Boston Bruins and Boston Celtics play) has undergone a lot of renovations. It is really amazing. I have to say that it is one of the best arenas I have been to and the atmosphere is incredible. If I was a visiting team I would be pretty intimidated by their game ops and wild fans. We had an awesome night and the game was suspenseful with a result we preferred (Leafs won!).

On Saturday morning we took the kids on a big walk and played at the Boston Common. The “Frog Park” was great for George. Perfect for toddlers and bigger kids. We had the whole place to ourselves. Boston is such great city for healthy lifestyles. Everywhere we looked people we being active and enjoying the spring weather. Have I mentioned how much I love Boston?

We hit up Legal Seafood for lunch (got my lobster roll fix) and then hit the road. Around Utica, NY the kids were really restless so we booked in at the Delta and stayed over. A great hotel for an impulse booking! I feel like we need to plan a visit to Utica as it has a children’s museum that looked great. Maybe we schedule a stop there on our next trip through New York State?

Sunday morning we got up and headed for home. Made a few stops but basically focused on getting home. By this point the boys seemed to have gotten accustomed to the car and were in the rhythm – right in time for us to get home!

Some things we discovered that may be helpful on your next roadie with kids:

  • Pack 10x the snacks you think you will need.
  • Don’t underestimate the power of a rest stop for providing enough of a change in scenery for the kids.
  • Be patient.
  • Bring your singing voices.
  • Leap Frog tablet helped a lot (I don’t have the one with the screen, just the one with books). We actually made it through the whole weekend without any Paw Patrol or screen time. I would have been open to it if we needed it desperately but we were able to do it without.
  • I wish I had brought blankets for the boys for the carseats. I feel like they would have slept better with them.
  • Take your time. Stop at Target. Don’t be afraid to buy a bunch of stickers and let your toddler stick them all over their body (this bought us about 25 minutes of silence).
  • Play i-spy.
  • Snacks. Cannot understate this.
  • Don’t be afraid to change the plan. We didn’t plan on stopping in Utica. We really wanted to make it to Syracuse but we listened to the screamers in the backseat and took our cue from them.

Must pack items:

  • Change(s) of clothes
  • Diapers/wipes
  • Munchkin disposable placemats (I discovered these on the trip and I can’t say enough about how handy they are). Pic below.
  • Leap Frog
  • Duplo and stacking cups
  • Snacks (I did Made Good granola bites, cheese sticks, clementines, berries and pouches)
  • Your enthusiasm. The kids pick up on everything. If you are excited about the windmill farm on the right side of the road, they will be too. Try to keep the energy up and they will feed off of that.