What I Learned Traveling to 10 Countries Before My Baby Turned 2
When I was pregnant, I heard it on repeat: “Travel now, because once you have kids, you won’t go anywhere.” Cue me laughing (and maybe crying a little) while stamping my baby’s passport for the 10th time before she turned two.
Spoiler: babies can be incredible travel companions — if you set yourself up right.
From London to Belize, yacht charters in Greece to pasta-filled days in Tuscany, here are the biggest lessons I learned hopping across 10 countries with a baby under two. Hopefully, they’ll save you a little stress — and inspire you to book that trip instead of waiting “until they’re older.”
1. City Breaks Are Easier Than You Think
Lesson Learned: Cities are actually baby-friendly when you know how to do them. Wide sidewalks for strollers, endless parks, and plenty of cafés where nobody minds a pram parked next to your cappuccino.
In London, we spent mornings in playgrounds, then wandered museums during nap time with the stroller. In Barcelona, tapas dinners worked because they start late anyway — baby slept while we ate.
Insider Tip: Book a centrally located hotel so you can pop back for naps. It saves your sanity.
2. Islands Don’t Have to Mean “Wait Until They’re Older”
Lesson Learned: Greek islands aren’t just for honeymooners. Locals adore kids, and the slower pace works beautifully with a baby’s routine.
Tinos had quiet beaches where baby could crawl in the sand without crowds, while Mykonos gave us the glamour but with family-friendly villas.
Insider Tip: Greece is stroller-optional. A baby carrier is easier for cobblestones, stairs, and ferry hopping.
3. Yacht Charters with a Baby Are Totally Doable (and Magical)
Lesson Learned: Yes, you can take a baby on a yacht. It’s not just for champagne-popping couples.
Our charter in Greece came with a crew who doubled as baby entertainers. Calm coves made swimming stops easy, and nap time happened in the cabin while we sipped rosé up top.
Insider Tip: book with us and we’ll be sure the charter includes a pop-up travel crib And add baby-proof mesh railings.
4. Don’t Sleep on the Caribbean
Lesson Learned: The Caribbean and Central America are basically built for family travel. Short flights, warm weather, and resorts that actually welcome babies.
In Turks & Caicos, Grace Bay was like a giant baby pool. In Belize, we mixed beach days with gentle jungle adventures. And Mexico’s luxury resorts rolled out everything from cribs to puree menus.
Insider Tip: All-inclusive isn’t just convenient, it’s sanity-saving when you’ve got a baby who snacks every 10 minutes.
5. Italy With a Baby? Absolutely.
Lesson Learned: Italians might love babies more than pasta — and that’s saying something. You’ll never feel more welcomed traveling with a little one.
In Tuscany, vineyard lunches stretched on while waiters happily bounced the baby. Wide-open countryside meant plenty of stroller naps while we explored.
Insider Tip: Skip the jam-packed city schedules. Base yourself in one villa and take day trips so you’re not constantly packing and unpacking.
6. Long-Haul Isn’t Off-Limits (If You Plan It Right)
Lesson Learned: Babies under two often fly for free (or a small percentage of the fare). They also sleep a surprising amount on planes. With the right prep, long-haul isn’t the nightmare you think it is.
We managed overnight flights where baby slept most of the way. Landing somewhere far-flung felt like such a win.
Insider Tip: Book bulkhead seats if possible (for bassinets), and always pack twice as many snacks, diapers, and outfits as you think you need.
7. The Baby “Window” Is Real — Use It
Lesson Learned: The under-2 stage is actually prime travel time. They’re portable, they nap on the go, and they’re not yet demanding playgrounds or chicken nuggets at every meal.
Our easiest trips were before walking. Once the toddling started, we had to level up our game.
Insider Tip: Don’t wait for “someday.” Book the trip now. You’ll never regret the memories (but you might regret not going).
Final Thoughts:
Take the Trip
One thing i learned traveling with both of our babies…. don’t be afraid to break “the schedule”. my oldest was a terrible sleeper - which actually made it easier to travel. we weren’t afraid of ‘ruining’ his sleep schedule. If he wasn’t napping or sleeping through the night at home, why not do it on the other side of world?! then my youngest came along and she slept incredibly from the get-go… we still traveled and she still slept.
Here’s the truth: traveling with a baby is different, yes. But it’s not a reason to stay home. The memories you’ll make — your baby’s first gelato in Tuscany, their first dip in Caribbean waters, their first nap on a yacht while the Aegean sparkles around you — are worth every bit of packing stress.
And if you’re not sure where to start? That’s where I come in. I know which London hotels deliver a crib and blackout curtains, which Caribbean resorts actually have high chairs at every restaurant, and which Greek villas have baby gates already installed. Because family travel doesn’t have to mean giving up luxury — it just means planning it smarter.
