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.

All our bags are packed and we’re ready to go…

Anyone sing that title in their head? Just me?

I’ve been doing this instagram/blogging/social media thing for about a week and a half. I don’t know what I am doing but I’m loving the learning element and I am really finding most people out there to be supportive and interesting. I have completed 90% of our packing (the last minute stuff like bottles, etc need to wait until literally the last minute). I can honestly say that I am pretty much the most excited I have ever been about our upcoming adventure.

There are a few reasons for this.

  1. It is Harrison’s first time overseas! I can’t believe we waited until he was almost 5 months. Considering he had a bit of a rough start (spent the first month of his life in the NICU) I am happy with waiting but I have been dying to watch a new continent through his eyes.
  2. We haven’t been overseas since last Fall! AHHHH!!! Nothing like an overnight flight and a taste of everything that is wonderful about Europe (WINE, CHEESE!!!) to re-energize you and make you feel alive.
  3. I am going to have so much content! SO.MUCH.CONTENT. I can’t wait to share our experiences with you and to continue this living, breathing record book for my boys to have forever.
  4. My hubs. I get to have him completely when we are away. No work (a few check ins here and there), no odd jobs around the house, no sporting events with his friends. I get to have him all to myself. I know the boys feel this way too.
  5. George. Swimming. That is all. Literally, the boy loves the water and to be able to give him a pool/ocean all day everyday for two whole weeks makes me so happy.


What is your favourite part about the pre-trip?


I’m not going to lie and say this week has been a dream. I have literally ran non-stop from the moment my feet hit the ground out of bed until I collapse getting everything organized for our trip and for when we get back (back to school, etc). BUT, that being said, the reward is there…dangling in front of me. A glass of vinho verde¬†and a beautiful sunset in Portugal await!


Travelling with a Toddler – The Carry On List

Now that our first little one is bigger and can eat everything (and I mean everything), you’d think travel would be easier. No bottles to pack, no sippy cups, no pacifiers, etc. Wrong. I still find that you need a full blown strategy to survive even the shortest flights with a toddler. Our little guy (2.5 years) has strong opinions, a big appetite and an allotment of energy meant for a marathon runner. Here is how I set us up for success on flights (short and long haul).

  1. Snacks. Goes without saying but honestly you can’t have enough. Airline food is typically BLAH, overpriced and if you are on Rouge or Air Canada Economy where you have the option to buy it you better hope you are in the first couple of rows. We have been on countless flights where everything has been sold out by the middle of the aircraft. I pack pouches (for the lack of mess factor). Typically I get apple sauce pouches from Costco and fruit and veggie ones from the grocery store. I also pack Made Good bars and bites. If you haven’t tried them they are ridiculously good (and relatively healthy) granola bar based snacks. Some have chocolate but most have dried fruit. My kid LOVES them. I pack extra as the hubs tends to dig in too. Another ¬†thing I do is I usually stop at the stores after security and grab some yogurt, maybe a muffin or a bagel and some fruit. We also typically go into the lounge as hubs has status and I grab bananas or other fruit pieces there. I know we aren’t supposed to take them but I do anyways. Whoops!
  2. iPad + headphones. Yeah, obvious right? But a couple of tips. One, I usually stop allowing TV or any shows at all leading up to travel days. This makes it extra special for the trip and makes it exciting. Two, get wireless earphones. I honestly swear by ours. LilGadgets Untangled Pro is the model. We charge them (you can also plug them in when in use) and that way the cords don’t get in the way of a fidgety toddler. They connect by bluetooth to the iPad. Three, Netflix. Download everything you possibly can so that it can be watched without wifi. Netflix literally saves my life.
  3. Stickers. Not your average stickers. Source out reusable stickers from dollar stores or walmart or target. Wherever. I honestly can’t tell you how many hours have been wasted sticking and resticking dump truck stickers to plane windows and fold down tables. They also come with a surface for all of the germaphobes. I keep telling myself my kids are going to have the best immune system going.
  4. Dollar Store Stuff. Literally, before a trip I drop a bunch of cash on stuff I really don’t care about that is small that we can fit in our bags. Think, tiny plastic dinosaurs, toy cars, etc. I don’t care if we lose one under a seat and typically we loose more than one. I hide them until the flight and then slowly introduce them as needed. I also buy the invisible ink markers that come with themed colouring books (they come in a mini size at the stores near me). Usually Paw Patrol based. this works for at least 20 minutes of fun.

I also pack a ziplock bag with one diaper for every 1.5 hour of flight time (you never know when one might break, or a poosplosion might happen). Delays also get you and you might be limited in size options at an airport. I bring one pack of wipes to share between both kids. Usually one extra pair of clothes. Typically the lightest I can find. Often a pair of PJs.

Hope this helps! I will follow up with a post on what I pack for my 4 month old!