Did you know my son, Jonny, took his first plane ride when he was two weeks old? Yes, we traveled to Phoenix, and he didn’t even cry once. We have been traveling since the boys were in diapers through this year when we are going to Turks & Caicos before Duncan leaves for college. Family vacations are a great way to reconnect.
Planning a family vacation can feel like a high-stakes game of travel Tetris—trying to align nap schedules, energy levels, screen-time limits, and snack preferences into one cohesive, joy-filled journey. But the truth is there is a perfect destination for every family at every age. Whether you’re toting a stroller, wrangling toddlers, guiding curious grade-schoolers, or trying to entice a teen off their phone long enough to look up and say “whoa,” we’ve got you.
Here’s your go-to guide for family-friendly destinations, tailor-made to delight everyone from new parents to seasoned travelers with college-aged kids.
👶 Infants & Babies (0–2 years): Peaceful, Low-Key Escapes
Best Destination: Hawaii (Maui or Kauai)
Babies don’t need much—just a soothing rhythm, a comfy stroller, and a relaxed vibe. That’s why Maui and Kauai are ideal. Think gentle waves, stroller-friendly resorts, and tons of nature with zero pressure to see everything. Stroll through botanical gardens, nap poolside, and watch the sunset with a mai tai in hand—you earned this.
Runner-Up: Amalfi Coast, Italy (because if the baby’s going to nap in a carrier, you could do it with views of Positano and plates of handmade pasta).
🧒 Toddlers (2–4 years): Playful and Safe Adventures
Best Destination: Costa Rica
Welcome to the “why?” phase—where your curious little explorer wants everything explained and touched (and sometimes licked, let’s be real). Costa Rica is a toddler wonderland with monkeys, waterfalls, colorful birds, and toddler-sized thrills. Stay at a family-focused all-inclusive like Dreams Las Mareas with short hikes, soft sand beaches, and splash-worthy pools.
Runner-Up: San Diego, California—because of LEGOLAND + beaches + the San Diego Zoo = toddler gold.
🧒🏽 Early Elementary (5–8 years): Wonder & Whimsy
Best Destination: Walt Disney World, Florida
School-age kiddos are the golden age of imagination. Fairytales are real. Princesses are real. Lightning McQueen is absolutely, 1000% real. Disney World is pure magic for kids in this age group—and with the proper planning, it’s fun for grown-ups, too. Stay at a resort on the monorail for easy nap-time escapes and character breakfasts. I recommend Disney’s Polynesian Village or Grand Floridian Resort & Spa; both offer tons to do at the hotel. When we went to Disney World for Duncan’s Kindermoon, there were days we never left the resort.
Runner-Up: Ireland—for castles, leprechauns, wide open spaces, and friendly faces everywhere you go.
👧🏽 Tweens (9–12 years): Active & Curious
Best Destination: Japan
Tweens are about novelty and adventure—think futuristic cities and ancient temples. Japan strikes the perfect balance of safe, organized, and delightfully weird (Robot Restaurant or live Mario Cart Races through Tokyo, anyone?). They’ll love riding the bullet trains, slurping ramen, visiting sumo stables, and picking out bizarre KitKat flavors at 7-Eleven.
Runner-Up: London, England—for Harry Potter vibes, double-decker buses, and leisurely walks through history.
👦🏾 Teens (13–17 years): Culture, Thrills & Wi-Fi
Best Destination: South Africa
Teens crave adrenaline, authenticity, and a chance to snap that one jaw-dropping pic to flex on their friends. South Africa is epic: safari drives, Table Mountain hikes, beaches, penguins (!), and rich cultural immersion. Bonus: teens are old enough to appreciate the impact of travel here, and there’s less whining about the length of the flights!
Runner-Up: Iceland—hike glaciers, explore lava tubes, chase waterfalls, and soak in geothermal lagoons while pretending to be in a Viking saga.
🎓 College-Age Kids (18–22): Bucket List Bonds Before They Launch
Best Destination: Thailand
A trip with your college-age children is the “one last hurrah” era—your baby is grown, your days of booking adjoining rooms are almost over, and it’s time to go big. Thailand is adventurous yet approachable. Snorkel in Phuket, explore temples in Chiang Mai, breakfast with elephants in Chiang Rai, and eat through Bangkok. You’ll bond over bucket list moments; they might even post about it without being asked.
Runner-Up: New Zealand—road trip heaven with jaw-dropping views and enough action-packed activities to get them off TikTok for a minute.
Every season of parenthood brings different challenges—and different kinds of joy. The best family vacations honor your kids’ unique needs and your desire for connection, wonder, and maybe a little room service.
Want help picking the perfect destination for your crew’s current stage of life? I’ve got you. Let’s build a family trip that makes everyone say, “Can we do that again next year?”
