Take Your Toddler Trips with Intention

I chatted with Platonic Love co-founder and fellow toddler mom Aliza Sir about her travel strategy with her two-year-old.

Every month, I’ll be bringing you interviews from travel experts/caregivers from around the globe as part of Travel with Toddlers—because as we all know, every! kid! is! different! I want to include a wide range of voices here, so if you or someone you know would like to be featured, comment/reply and let me know.

Today’s guest for our newsletter is one I’m super excited about: Aliza Sir, from Platonic Love. I’ve been reading that newsletter since its inception—mainly because I professionally know Aja Frost, Aliza’s co-founder, through the tiny Boston tech community—and it really is one of my favorites on Substack.

Aliza and her family on Martha’s Vineyard.

I look forward to their thought-provoking issues on friendship, motherhood, and life in your ‘30s in my inbox every week. Aliza’s posts on motherhood are particularly relevant to me because her son, Jude (2), is close in age to my own toddler, so we are often going through the same phases (and by extension, the same motherhood phases) at the same time.

Aliza Sir on Travel with Toddlers

But really, the way she writes makes me feel so seen.

My first run, on a sunny 70-degree day in early November, felt like trudging through mud. I tried giving myself an internal pep talk. You’re doing it! That’s all that matters! I breathed. Pain shot through my hips, as if they might collapse inwards, and my core ached. I looked at the time on my phone: not quite 10 minutes had passed.

After five more, I turned around and walked home. “How did it go?” Sam asked as I walked in the door.

“Awful,” I said. “I felt like shouting, ‘I had a baby eight weeks ago!’ to anyone who passed me.”

I had this EXACT experience, and continue to feel surprised at how long it took me to recover from that period, and how I’m still building back my physical endurance. Part of why I started this newsletter is I feel like travel media either pressures you to start traveling right away (Don’t let a baby stop you! babies are so portable! lololol) or there’s so much fearmongering (You’d bring your toddler to X destination? They won’t even remember it!) that I wanted something real.

Here’s how Aliza approaches traveling with her toddler:¹

How has your travel “style” changed before and after having kids?

I always have a trip on the calendar that I can look forward to. I spent a lot of my ‘20s traveling for work, which allowed me to add-on trips to explore parts of the country I’d never been before. I convinced my dad and sister to meet me in Flagstaff, Arizona, once, and picked them up to go to the Grand Canyon and Antelope Canyon after a conference before we all flew back to where we live—I live in Boston, my sister lives in Minnesota, and my Dad is in Nashville where I grew up. It was one of the best weekends I can remember, and it’s one of the reasons I love traveling. You can get out of your head and your day-to-day routine for a little bit.

Travel has always been energizing for me, especially planning the trip. That hasn’t changed much since I had my son, since it’s so core to who I am. But what has changed is thinking really intentionally about when we are going to bring him as a family.

What am I trying to achieve from this trip? Because if I’m envisioning that we’re going on these long hikes and doing the types of things I did before I had my son, that’s not going to be feasible. I get to decide what’s going to make this travel opportunity feel good to me, and it looks different than it did before. (Editor’s note: This is SUCH good advice and I feel like it applies to most of parenting principles.)

Tell me about the first trip you took after you had your baby.

Our first trip was when Jude was a month old. We booked an Airbnb in Brattleboro, Vermont, which is a two hour drive from us in Boston. We went just for one night. I mean, we spent an entire day packing up the car because we had no idea what we were doing. But I’m so proud of us for taking that trip as first-time parents when he was so little.

Ugh, Vermont is just so pretty.

It was a really nice trip. We put him in the carrier, we went out to lunch, we went for a short hike. I nursed him at the top of a “mountain,” more of a large hill, really, and we went to this bar and had drinks and dinner while he was sleeping in his stroller. That was the first time we had done any of that.

It felt important for me to do that because we took eight weeks of parental leave together, and I didn’t think we’d have another opportunity for all three of us to go do something like this. It was 24 hours, and we came back exhausted, but for me, it felt like I needed to prove to myself that it was going to keep getting easier, and that I could do it.

Your baby will surprise you.

With a baby, don’t overthink it too much. Of course every child is different, and you know your own child, but they are so adaptable, and they surprise us all the time. Anytime our son slept in a new location, or met someone new, he just rolled with it. If traveling is something that is important to you, then you can do it. You’ll start to see when it’s worth it and when it’s not. There’s so much I’ve personally gotten out of traveling with my son, and because I have family out of state, it’s something we have to do regularly, so it’s important.

That’s true now that I have a toddler, too. It’s so different already. Our second trip we took when our son was a baby was to visit family in Nashville when he was three months old, and he slept the whole time. That’s not the case anymore. (Editor’s note: Don’t I know it…last time we flew we gave up and watched Encanto twice in a row. I’m STILL singing We Don’t Talk About Bruno)

The gear Aliza doesn’t leave home without…

I used to be more of a weekend warrior and just throw my stuff in a bag and get on a plane, but I don’t have that kind of endurance anymore. I travel less because of how much stuff you have to bring.

Logistically, some things I had to let go. I know there's some parents that can still do carry on suitcases, but we let that go.

I got a bigger suitcase from CalPak and I use packing cubes (Aliza recommends these Herschel ones; I have these ones from Amazon) to divide half the suitcase for myself and half for my son, and my husband packs a separate bag, which works for us. We pack all of the sleeping stuff and diaper stuff together, so that when you get to where you’re going, everything you need immediately is ready to be pulled out. The other trick I recommend is just traveling with the number of diapers you need for five or six hours, and then buy them when you get there, or ship them ahead of time.

We also love our travel stroller, which is the Nuna TRVL. (Editor’s note: I was choosing between that one and the one we went with, the Babyzen Yoyo2. Both are super pricey but SO worth it.)

The best destination to travel with toddlers is…

Toddlers and farmers markets just go together.

My favorite place I’ve been with my son is definitely Martha’s Vineyard. We spend a lot of time there in the summer. Obviously going to the beach is a lot of fun, but they also have amazing libraries and playgrounds. There’s so many great restaurants where you can just sit outside and be messy. And I love that. We spend most of our time on Martha's Vineyard up-island, the smaller and quieter part of the island than the down-island towns like Edgartown and Oak Bluffs:

• West Tisbury Farmer's Market: Rain or shine, Wednesdays and Saturdays from 9:00-noon starting in June. Brings together all the best farms and other vendors on the island. My two-year-old loves the live music too!

• West Tisbury Public Library: This library is located centrally on the island, close to the Farmer's Market and sandwich shops like 7A, plus there's an incredible children's room with — in addition to books — tons of things like crafts, toys, and puppets. We especially like to walk into the gardens behind the library and visit the miniature house.

• Menemsha: The small, working fishing village is a can't-miss spot on the island. Some of our favorite spots include The Galley (for soft serve and chocolate malts) or Larsen's Fish Market on the way home from the beach to eat raw oysters, lobster rolls, and fresh boiled lobster outside on "benches" (aka old crates).

• Lobsterville Beach: This is one of the few "dog friendly" beaches year-round (definitely my dog Oliver's favorite place in the world). There aren't a ton of parking spots, so we usually like to go in the early mornings or late afternoons for sunset. The calmer water on this side of the island is also great for small kids.

Looks like heaven on Lobsterville Beach in Martha’ s Vineyard.

• Lucy Vincent Beach: Beautiful in the summer, but this is also a great spot to visit off-season, when you don't need a resident parking pass and dogs are allowed too.

Finally - another Substack that I like to follow for local MV recs is called @ MVacay!

Tell me about a great travel memory with your kids.

Jude’s favorite party trick all summer long.

It’s a lot of effort, but it’s so fun. One thing we figured out this summer on the Vineyard is that our son loves raw oyster shells, which cracks me up. He first tried one when we went up to Essex for Mother’s Day lunch and walked around. I wanted oysters, and of course Jude wanted to try anything on my plate. We don’t give him the actual raw oyster, but he loves to suck on the shells, which has been our party trick for the whole summer and it just makes me laugh. 🦞

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Thank you, Aliza! I love, love, love the idea of being more intentional on our trips. Why do we want to go to a certain destination, and will it *actually* be fun to bring a toddler? It’s such a helpful framework as we plan out our year of travel—we have a TON of family and friend weddings this year, so I’m sorting out which ones we’ll make a trip out of and which I might go solo.

On to this week’s recommendations!

This week’s rapid-fire recs.

Disclosure: This section may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. I promise I’ll only ever recommend products I’ve actually used and loved.

• One of my favorite essays from Aliza: 18 things you don’t have to care about as a mom.

• What to do with all those leftover cardboard boxes with your toddler. We are BIG fans of the sound crayons make on cardboard, but my toddler insists on sitting in whatever box it is, no matter how small.

• Love this 🦩 metaphor for coming out of the baby trenches. (NYT Gift Link)

• Our diaper bag has totally given up, and looking at Aliza’s packing cube rec made me go down a huge Herschel rabbit hole…this looks SO classic without screaming diaper bag to me.

• This made me crack up it’s so real. (I don’t think it’s limited just to boy moms, though!)

• How to help victims of the L.A. fires.

Thanks for being here.

I feel like chatting with Aliza gave me fresh eyes on a few of the trips I’m planning this year. Do I want to be the type of person that feels like we *have* to go on a spring break every year because we did last year? Could we handle an eight-hour flight to California to visit friends? Should we bring our toddler with us to three different weddings this summer? Right now, I’m still very much in planning mode.

Otherwise, we’re getting my toddler on skis for the second time ever next weekend…wish me luck! It’s important to me living in New England that my toddler is comfortable on downhill and Nordic skis, even though I can’t downhill ski really at all (my entire inner monologue is just PIZZAPIZZAPIZZAPIZZA!!!) Lots of well-meaning neighbors, friends, and family have told us now is the time to get on skis (at 2.5) but I am skeptical. We’ll see where we fall on the fun/worth it scale and I’ll report back.

Happy trails,

Kayla

Thank you for supporting Travel with Toddlers! If you liked this issue, please like it, share it, subscribe, or you can buy me a coffee. It really does mean a lot. I’m just a mom in the thick of the toddler years trying to create core memories for our whole family while minimizing meltdowns—I sincerely hope this helps you do the same.

1. This interview has been lightly edited for brevity and clarity.