Where We Loved Traveling with Kids Ages 3–6

(And What Actually Made It Easy)

Traveling with kids between the ages of 3 and 6 is a sweet spot — but it comes with its own unique set of challenges (AND joys!).

They’re no longer babies, but they’re not exactly “go with the flow” travelers yet either. Attention spans are shorter, walking stamina is limited, and how a destination feels matters just as much as what there is to see.

After traveling extensively with our kids during these years, these are the places that truly worked for our family — not because they were trendy, but because they were easy, engaging, and genuinely enjoyable for everyone.

🇮🇹 Italy

Italy remains one of my favorite countries to travel with kids — if you do it the right way.

What made Italy work for us:

• Walkable towns with piazzas where kids can move freely

• Casual dining culture (no one bats an eye at kids at dinner)

• Trains that eliminate long driving days

• A slow rhythm to life that encourages lingering rather than rushing

We focused on smaller bases — lakes, countryside, and slower cities — and skipped one-night stays. Gelato breaks, boat rides, and time outdoors mattered more than checking off sights.

Italy with young kids is less about seeing everything and more about enjoying where you are.

🇬🇧 London

London is unsurprisingly our favorite destination - and usually, on any list i’m going to share…. but for family-friendly cities we’ve visited it still reins supreme!

Why it worked so well with kids ages 3–6:

• Parks everywhere — perfect for breaks between sightseeing

• Museums that feel interactive and approachable

• Easy public transportation

• Familiar food options mixed with cultural experiences

London always feels exciting without being overwhelming, and it allows you to mix “big city” energy with lots of downtime. It’s a fantastic introduction to international travel for young kids!!!

🇺🇸 Chicago

Chicago is an underrated gem for family travel.

What made it easy:

• Flat, walkable neighborhoods

• A lakefront that feels like a beach day in the city

• World-class museums that actually engage kids

• Family-friendly dining without sacrificing quality

• Pizza + hot dogs are a food staple here….

Chicago gave us the benefits of a major city without the intensity. It’s a great option for families who want culture, food, and fun without overcomplicating logistics.

🇺🇸 San Diego

San Diego is one of those destinations that just works for families — and staying at Hotel Del Coronado made it feel extra special.

Why it stood out:

• Beachfront location (no packing up to go anywhere)

• A laid-back pace that suits young kids

• Sunshine, open space, and easy days

• A classic resort feel that still feels relaxed

This was one of those trips where everyone felt restored — and that’s rare with young kids.

🇹🇭 Thailand

Thailand surprised us in the best way.

Traveling here with young kids worked because:

• Warm, welcoming culture toward families

• Incredible service and hospitality

• Spacious accommodations and resorts designed for downtime

• A natural balance of exploration and rest

Thailand required thoughtful planning — but with the right routing and pacing, it felt enriching rather than exhausting. It’s a wonderful option for families ready to go farther, without sacrificing comfort.

🇲🇽 Mexico

Mexico has been one of our most reliable family travel destinations.

Why it works so consistently:

• Short travel times from the U.S.

• Family-friendly resorts and hotels

• Warm weather and outdoor living

• Flexible days that don’t require constant movement

Mexico is ideal when you want an international feel with minimal friction — especially during these younger years.

What Actually Made These Trips Easy

Across all of these destinations, a few things mattered more than the destination itself:

• Staying in one place longer

• Prioritizing walkability and transportation ease

• Balancing kid-focused moments with adult enjoyment

• Leaving room for unstructured time

At ages 3–6, travel doesn’t need to be ambitious to be meaningful. It needs to be thoughtful.

Planning Family Travel

Every family travels differently — and that’s exactly why cookie-cutter itineraries rarely work.

I help families plan trips that:

• Feel special but manageable

• Work with kids, not against them

• Balance culture, rest, and fun

• Take the stress out of logistics

If you’re dreaming about your next family trip and want help designing something that truly fits your family, I’d love to help.