People often ask which destinations actually work with a toddler, assuming the honest answer is "none of them, stay home." It isn't. Freddy has now done three continents, camping, multi-day hikes and long-haul flights before turning three, and every single destination taught us something different about what actually works.
Here's the honest ranking, from easiest starting point to the most ambitious thing we've done.
Barbados — The Easiest Starting Point
If you're nervous about your first trip with a toddler, start here. Calm beaches, warm water, no jet lag if you're coming from similar time zones, and a culture that is genuinely warm towards children everywhere you go. It's forgiving in every way a first toddler trip should be.
Read the self-drive island tour and Barbados packing list to plan your own trip.
Scotland — West Highland Way
Freddy hiked sections of the West Highland Way at two years old — specifically the Tyndrum to Fort William stretch — carried in a good structured carrier with short stints on his own feet. Scotland's weather is unpredictable, but a toddler genuinely doesn't mind rain the way adults do, and the scenery makes up for whatever the sky throws at you.
Read the full West Highland Way itinerary and packing list.
Free Download
Free Toddler Adventure Packing List
Everything I carry for me and Freddy — tested across three continents.
Iceland — The Road Trip Test
A campervan road trip around Iceland's Ring Road works surprisingly well with a toddler — the driving days give built-in nap time, and the landscape is dramatic enough to keep everyone entertained during the awake stretches. The unpredictable weather and long driving distances make it a step up from Barbados in terms of logistics.
Read the full Iceland road trip guide.
New Zealand — Big Country, Flexible Pace
New Zealand rewards a slower pace with a toddler than the typical backpacker itinerary. The distances are bigger than they look on a map, which actually suits toddler travel well — nobody's rushing, and the driving days double as rest days.
Read the Ultimate New Zealand Travel Guide and Driving in New Zealand.
Patagonia — The Big One
Three weeks across Chile and Argentina, camping, long drives, genuinely unpredictable weather, and Freddy at three years old handling all of it better than either of the adults some days. This is not a starting point for toddler travel — it's what you build up to once you've got a few easier trips under your belt and trust your instincts about what your specific toddler can handle.
Read the Complete Patagonia Travel Guide and Patagonia Packing List.
Building Up Gradually
Start with something forgiving like Barbados before attempting something as demanding as Patagonia. Confidence, gear knowledge and a genuine read on what your toddler can handle all build trip by trip — don't skip straight to the hardest thing on this list.
The Honest Truth About Toddler Travel
Every destination on this list taught us something different. The flights were harder than expected and also more manageable than expected, simultaneously. Read the flying long-haul with a toddler guide for the full honest account of what that actually looks like.
The trip you're most nervous about is often the one that turns out best. That's been true every single time.
Free Download
Free Toddler Adventure Packing List
Everything I carry for me and Freddy — tested across three continents.
Related Posts
Frequently Asked Questions
Barbados, if you're coming from the UK or similar time zones — no jet lag, calm beaches, warm water, and a genuinely welcoming culture around children. It's the destination we'd recommend to any parent nervous about their first trip with a toddler.
