[06.26.24] Just over a year ago, I started Carry On. This newsletter, all about the transition to traveling as a parent, is the result of a decade-long corporate career that has led me to want to build something for myself, a lifetime of prioritizing travel, and the unlocking of a forgotten creative part of my brain that revealed itself after becoming a parent.
Carry On now has more than 180 subscribers! How incredible. It is so exciting when someone new subscribes. Thank you to everyone who reads, provides feedback and supports this project <3
Today: planning a Europe trip with a toddler (again) & the 3 things I’ll be doing differently this time around.
Only nine months ago, late last September, I kissed the ground at Heathrow Airport when we eventually landed in London after the single longest flight of my life.
It was not my longest flight as measured by hours. Dubai to New York circa 2018 holds that title. But this ten hour period was second to none in my perception of just how long a flight could feel.
Why? My 16-month-old daughter refused sleep, in dramatic fashion, the entirety of the ten hour overnight flight. Groggy, sleep-deprived and feeling like failures, we stumbled onto a connecting flight to Mallorca to kick off our first family trip abroad.
Why then, you might ask, would we sign up for the exact same flight a mere nine months later?
Well, I certainly didn’t expect to be back in Europe with our daughter so soon. A confluence of factors came together for us to be in this position.
First, my sister- and brother-in-law moved to London! Automatically a great reason for a trip.
Upon learning they were moving, Joe and I immediately began discussing the best time to visit. As logic would have it, the best time to visit would be before we had another kid.
Being that we would like to have a second child in the not-too-distant future, the answer of when to visit became “as soon as possible!”
So we booked tickets to the UK and tacked on a visit to one of the most child-friendly European countries, Portugal; it will be my third time visiting both countries, first time in the northern part of Portugal.

Now, I don’t know about you but for me, when it rains, it pours.
After years of softly searching and months of seriously looking, we are currently buying a house in Southern California. As fate will have it, we will leave for this pre-planned trip less than one week after we close on our home. Ha!
You could argue it’s poor timing. Yes, we will have to pack up and deal with moving as soon as we get back from vacation. Yes, travel is a superfluous expense right before we start plowing money into homeownership. However, in a strange way, it’s fitting.
I had some mental blockages around buying this house, as I fear settling down and losing my ability to travel. It’s similar to the fear I had about travel after becoming a parent - of staying so long in one spot that I would forget my connection to experiencing the world at large.
Logically, I know this fate can be avoided with thoughtful budgeting and good time management. This trip happening concurrently with buying the house has provided a jolt of confidence to my psyche; I have to believe it’s possible to step into the stable, new home that my parent-mind craves, while keeping my heart solidly in the world of travel.
The Basics
Who’s Going: Mom, dad, toddler (meeting my sister- & brother-in-law)
Child’s Age: 2 years (25 months)
Timing: late June - early July 2024
Trip Location: London + Northern Portugal (Porto + Douro Valley)
Reason for Trip: Vacation
Trip Length: 10 nights in accommodations + 2 travel days
3 Things We Are Doing Differently On This Europe Trip
First, it’s a multi-destination “trip-within-a-trip”, not a single destination.
My most infamous “trip-within-a-trip” was a proper exercise in inception.
Nine years ago, my brother was living in Madrid and, being recent college grads with little disposable income, we selected flights and destinations for our sibling trip simply by sorting for lowest price.
That “trip-within-a-trip” (-within-a-trip,-within-a-trip) entailed 8 flights in 10 days: New York > Stockholm > Madrid > Istanbul > Thessaloniki > Istanbul > Madrid > Oslo > New York.
That trip with my brother would be unfathomable to attempt with a small child, though I am grateful now that I had the opportunity to travel with my sibling in such a carefree way.


To avoid the challenges of moving around too much, we were intent on a single-destination trip for our first international family adventure last Fall. We chose Mallorca in order to maintain one lodging while experiencing different towns, beaches and activities.
It worked beautifully and, if anything, we could have stayed in the same place even longer and we would still have had more to do. I recommend the single destination approach, especially for a first big trip as a family.
For our second Europe trip, however, we are leaning into the confidence cultivated over 28 flights with our daughter to expand our horizons.
Without a doubt, this plan is more ambitious than last Fall’s trip to Mallorca. But still less so than a trip-within-a-trip could be. We will be taking 4 flights in 10 days: Los Angeles > London (1 night) > Porto (3 nights) > drive to Douro Valley (2 nights) > London (4 nights) > Los Angeles.
One thing I am looking forward to this time around is separating the transatlantic London flights from the intra-Europe Portugal flights, versus doing both in a single day.
There are zero direct flights from LAX to Portugal, so it would have required a layover to get to Portugal in one fell swoop. Moreover, boarding that flight to Mallorca following such a grueling, long flight to London was painful. I am expecting that we will be better set up for success with this trip structure.
That said, this “trip-within-a-trip” is made possible by lodging with family in London. If we didn’t have that option, I would likely have structured the trip to have only two portions. This would have required biting the bullet and flying with a layover to Portugal while lumping all days in London together on the back end. Generally, I am not a fan of a single night layover with small kids due to the disruption of setting up and breaking down baby gear.
I do worry that we won’t be able to fully relax with all of the movement on this multi-destination vacation. On the positive side, we get to stay in three different locations on one trip and make the most of our time away!
Plus, our daughter is a more experienced traveler than ever, so my confidence in her ability to adjust is high.
Plus plus, do we ever “fully relax” when traveling with a toddler, anyway?
Second, we strongly considered not bringing a car seat.
However, we ultimately decided to bring one. Here’s why.
With the days of lap infant behind us, we always do long flights by bringing Mila’s car seat on board.
Reasons TO bring a car seat on this Europe trip:
It’s the most secure place for a toddler to sit on the plane.
We know Mila is capable of sleeping in her car seat.
Avoid checking the car seat and risking possible damage.
Avoid the questionable quality of a car seat rental at our destination.
Reasons NOT TO bring a car seat on this Europe trip:
It’s one additional thing to carry.
We would get more seat space on the plane without a car seat.
We actually only need the car seat for 2 days in the Douro Valley.
Technically, American car seats are illegal in Europe. European car seats are not allowed to have the chest strap. Most people bring their U.S. car seats anyway.
Because we only need to use the car seat for a small portion of the trip, initially I figured we could rent one in Portugal and avoid lugging ours all the way there.
I started questioning this strategy when I realized that the Portuguese baby rental companies I was comfortable using, Babonbo or Let’s Go Baby PT, only service Lisbon and the south of Portugal.
We could theoretically rent a car seat from the car rental company, but I’ve heard too many horror stories about the seat being in poor condition or not the right weight limit for the specific child.
Then, I started thinking critically about the 10- and 11-hour flights to & from London.
We are flying United, an airline that is notoriously strict about disallowing seat extenders like the Flyaway Bed. I hypothesize that Mila will have an easier time sleeping in the known entity of her car seat, as opposed to a makeshift blanket functioning as a seat extender - a setup she has never experienced before.
It’s a prime example of “know your child”. Mila has never fallen asleep on the go in her stroller, nor anywhere beside her crib at home, her floor mat at school, and her car seat.
I could be wrong on this hypothesis. Worst case scenario, we will attempt to hold her to sleep. I remind myself that the sleep situation can not be worse than the last flight we took to London… here's hoping I’m right!
In case she does not sleep in her car seat on the way over to London, we will check the car seat on the long flight back home and pull together a makeshift seat extender with a blanket.
The beauty of having traveled with Mila from such a young age is that we know we can survive (and thrive) despite the hiccups. Sleepless redeye flights included.
*In a twist of fate, Mila refusing sleep on the flight to London last Fall led her to have a very seamless transition to the new time zone (+9 hours). Silver lining!
Third, we booked everything refundable.
Remember how I mentioned the best time to go on this trip would be before we have a second child?
We booked this trip several months in advance, when we could not know whether I would become pregnant before the trip.
Because I had a complicated first pregnancy and birth, I was only comfortable booking a cross-continental trip knowing that we would have the option to cancel just in case I became pregnant and if, for some reason, it wasn’t recommend for me to travel.
I did not want to have to decide between losing thousands of dollars on nonrefundable travel bookings versus traveling when it wouldn’t be safe to do so.
Financially, this was not ideal as the cost of refundable flights is noticeably higher than non-refundable, especially when booking twelve tickets (four flights, three passengers each).
We compared the cost of booking all flights refundable with the cost of booking flights non-refundable and buying Cancel For Any Reason (CFAR) travel insurance. Ultimately, it made more financial sense to book refundable and avoid travel insurance. Fun fact, CFAR insurance often only covers up to 75% of the incurred costs, not the full amount paid, and there is additional effort required in submitting evidence of the non-refundable purchases, should you make a claim. We also chose to limit Airbnb options to just those with flexible cancellation policies.
Although we did not end up tapping into the cancellation flexibility that we paid for, I find myself at peace with our decision to keep our options open when facing the unknown.
In a future newsletter, I will write about travel planning amidst family planning. There is so much nuance in deciding how/when to travel when you are hoping to become pregnant.
Also, speaking of the financial side of things - stay tuned for the transparent breakdown of this trip’s costs. The cost breakdown from our Mallorca trip was a hit and the topic of financing family travel is highly relevant for many of the new parents I know.
Thank you for reading! Know someone who travels, has kids, or is thinking about having them? I’d appreciate if you’d send Carry On their way 🙏🏼
p.s. you can always see all posts on the website
I’m so impressed! This is a big itinerary! It’ll be great. We just got back from a month in Portugal with our 13 month old— it’s such a fabulous place to be with a kid. If you are looking for a great hotel up north— try Octant Douro, great programming for the little ones too. Have a fab trip :)