The Perfect Two-Week Greek Island Hopping Itinerary With Little Kids
There’s something magical about the Greek islands — those whitewashed villages, turquoise waters, and salty breezes that make your shoulders drop two inches the second you step off the ferry.
Add to that how much Greeks genuinely adore little kids, and you’ve got the makings of a dream family vacation — servers bringing complimentary fruit, auntie-types fawning over my son’s curls, and zero side-eye when he gets a little loud at dinner.
If you’re looking for a Greek island itinerary that blends luxury, jaw-dropping beauty, and total kid-friendliness, let me introduce you to three of my favorite islands: Paros, Milos, and Santorini. Over two weeks, you’ll explore secret beaches by private boat, relax in resorts where the views are as dreamy as the service, and eat your weight in tzatziki.
Here’s exactly how we did it:
Days 1–5: Paros — Golden Beaches and Laid-Back Luxury
Start your adventure on Paros, one of the more under-the-radar Cycladic islands that somehow has everything — gorgeous beaches, charming villages, and far fewer crowds than neighboring Mykonos.
Where to Stay
We based ourselves at Andronis Minois (read our full review), which felt like the perfect blend of Cycladic architecture and coastal calm. Think white-and-stone suites, some with private pools and a breezy seaside restaurant with chairs you’ll melt into. The best part? They welcome families, and they get that traveling with kids means needing a bit of flexibility.
We booked the two-bedroom Blu suite which was perfect for us, with sunset views and our own private pool, in addition to the resort pool which had nice shallow areas that made parenting that much easier.
✨ Pro tip: We’re part of a travel agency! When you book Andronis Minois through us, you get the following perks at no extra cost to you (here’s more about who we are and how it works):
- Room upgrades when available
- $100 +Resort credit
- Early check-in & late check-out when available
- Full GHA Discovery loyalty points
What to Do in Paros with Kids:
- Wander Naoussa: This harbor town is as picturesque as it gets, and early mornings mean quiet strolls and bakeries full of still-warm spanakopita.
- Swim at Kolymbithres Beach: Shallow, calm, and framed by smooth granite boulders that toddlers will love climbing.
- Private Boat Trip: For around $400, book a half-day private boat tour that hugs the coast and stops at sea caves and secret beaches around Antiparos. Bring snacks and floaties and let your little ones nap under the sunshade as you cruise.
Days 6–10: Milos — Moon-Like Landscapes and Hidden Coves
Next, hop a quick ferry to Milos, which might just be Greece’s best-kept secret. The geology here is wild — lunar-like white cliffs, red sand beaches, and caves that look like they belong in a fantasy novel.
We stayed at Artemis Seaside Resort in the south, right on the water. It’s stylish without being fussy, and the family rooms are a dream — big enough to spread out and just a few barefoot steps from the beach. We can book families here too!
Milos Highlights:
- Sarakiniko Beach: It looks like the surface of the moon, and kids love the lunar rocks and shallow tide pools.
- Plaka Village: Grab a late afternoon gelato and take in the sunset from the castle — you won’t regret it.
- Another Private Boat Day? Yes, please. Again, for around $400, you can hire a skipper to take you to Kleftiko, a cove accessible only by boat, where the water is so clear it looks photoshopped.
It was honestly one of the most relaxing days we had — our son napped in the cabin, we swam in caves, and they even had snorkeling gear on board.
Days 11–14: Santorini — Iconic Views and Five-Star Perks
End your island hop in Santorini, the island that needs no introduction. Yes, it’s popular. Yes, it’s breathtaking. And yes, it’s still worth it — especially if you know where to stay.
I hadn’t realized prior to researching how difficult it could be to find accommodations that allowed children under 12 in Oia and Fira, the iconic towns with the sweeping caldera views and whitewashed buildings and blue domes. Given the steepness, I get it, and was so glad to find the hotel we ended up staying at, which ended up being one of our favorite luxury hotels ever.
Where We Stayed
We chose Canaves Oia Epitome (read my full review), which is just outside the chaos of Oia and feels like a secret hideaway perched above the sea. The infinity pool overlooks the caldera, the sunset views are iconic, and somehow — despite being ultra-luxurious — they still roll out the red carpet for families.
Our suite had its own private pool, and we didn’t even need to leave the resort to feel like we’d “done” Santorini.
✨ Book Canaves with us and enjoy all of this for no extra cost:
- Room upgrades when available
- Resort credit
- Early check-in & late check-out
- Full loyalty points with Hyatt or Hilton, depending on your program of choice
Next we moved to Fira for the best of both worlds, staying at a more affordable luxury option called Arressana Suites, where we can offer the same perks! Here’s how it looked:
The service was particularly great here, with kind staff and a real attention to detail, particularly for my son’s allergies.
Things to Do in Santorini with Kids:
- Cable Car or Donkey-Free Fira Walk: Fira somewhat is stroller-friendly early in the day, and the views are absolutely stunning, though we preferred a toddler carrier for ease.
- Swim at Black Sand Beach: Kamari is a good pick — rent loungers with umbrellas and grab smoothies while your toddler builds castles.
- Family Photoshoot: It’s worth it. The lighting, the backdrop, your tiny human in a floppy sun hat? You’ll frame these forever.
✨ Bonus Tip: Overnight at the Sofitel Athens Airport
Whether you’re arriving late or flying out early, the Sofitel Athens Airport is the easiest bed. It’s literally right across the street from the terminal — no shuttles, no chaos, just roll your stroller right in.
✨ Book through us for:
- Room upgrades
- €100 property credit
- Daily breakfast
- Early check-in and late check-out
Perfect for a soft landing before or after your island adventure.
Final Thoughts
Greece with kids is everything. The locals treat children like honored guests, the food is universally kid-approved (hello, saganaki and watermelon at every meal), and the pace is just right for slow mornings and sunset dinners. It’s one of our favorite destinations to travel to with a baby and I know we’ll be back soon.
This two-week itinerary gives you a taste of three stunning islands, and with luxury stays and private boat days sprinkled in, it still feels like a vacation for you, too.
And if you want help planning it all — from transfers to baby gear rentals to those amazing resort perks — I’d love to help. Just say the word.
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