Thanks to our contributor Jake Cain for sharing his amazing experience visiting Santorini with kids!
Once we knew our 3-week European adventure was going to start in Greece, I quickly tried to figure out how we could spend some time on the island of Santorini.
I knew it was one of the most photogenic places in the entire world and this was our chance to experience it firsthand.
The only hesitation was whether we’d be battling huge crowds in tourist hotspots like Oia and Fira, and leave the island feeling like we just starred in one of those “Instagram vs. Reality” videos you always see on your feed.
Fortunately, we figured out how to experience the iconic beauty of the island without being completely overwhelmed by the large crowds.
Here’s the story of how we stumbled into 4 days of Santorini magic and how to find the local experiences that most tourists miss.
What We Accidentally Found: A Village, Not a Resort
Our first clue that we’d tripped over something special came when we pulled up to Vedema, a Luxury Collection Resort (part of Marriott International) and realized that this didn’t feel like a hotel – it was more like a perfect little village. We were invited by the resort to experience their hospitality firsthand, and as soon as we arrived we knew we were in for something extraordinary.
We’d taken the ferry from Athens to Santorini and rented a car, which I quickly learned means navigating narrow cobblestone streets that aren’t for the faint of heart.
Based on my experience with “resorts,” I was looking for a grand entrance that you can’t miss, but Vedema is a totally different vibe. You pull through the charming village of Megalochori and up to the discreet entrance.
As you walk through the entryway, you realize this place is like nothing else you’ve ever seen. We were taken for a quick tour by the front desk staff, and around every corner was another “wow” moment. Stunning views in every direction, beautiful flowers, and stone pathways that seemed to lead to Instagram-worthy photo spots at every turn.
Our villa? Two bedrooms, private pool, with views of the Aegean Sea. But more than the luxury, it felt like we’d been dropped into a postcard with an overwhelming feeling of peace. No crowds, no over-the-top programming, just quiet luxury that lets you unplug and relax on one of the most beautiful islands in the world.
Why This “Accident” Was Genius for Families
Confession: I was a little worried about showing up to a “luxury resort” with three boys who think the height of sophistication is when we make them wear polo shirts to dinner. Would we be the only family? Would we get those looks? (You know the ones.)
Not even close. Turns out, Vedema Resort attracts multi-generational families—grandparents, parents, grandkids all mixing together in the pool. Nobody blinked when the boys jumped in and had some fun. In fact, the staff seemed to go out of their way to make us feel at home.
Every morning, we’d grab breakfast by the pool (yes, with actual blue domes in the distance, but without a crowd of selfie-takers fighting for the “right” angle). The food and coffee were both excellent, but we loved starting our day this way as we made plans for what else to see on the island.
The kids naturally wanted to explore the stone paths instead of asking for the WiFi password. Something about the medieval village captured their attention immediately, and they spent time enjoying the moment rather than reaching for a device.
The Cultural Experiences Most Tourists Miss
We’re not really a musical family, but we had a blast at the interactive music presentation with Yannis Pantazis at the Symposion Cultural Center. He demonstrated various ancient Greek instruments, many of which he built by hand, and got us involved playing percussion and harp alongside him. It was an excellent combination of laughing and learning, set in beautiful Megalochori Village just a short walk from our resort.
Then there was the Tomato Factory tour. The kids thought it sounded like a snooze compared to staying at the pool, but our guide wove together her family’s story with Santorini’s agricultural past, which really made the place come alive. There were several interactive exhibits where you can get a sense of what it was like working in the factory, long before Santorini became an Instagram hotspot.
But the highlight? Vedema Resort arranged for a chef to come to our villa and cook a small Greek feast for us. He explained the history of every dish while we watched and drooled. I’ve never seen my kids eat so much, or listen so intently to someone talking about olive oil.
The Food Discoveries That Made the Trip
If you’re staying at Vedema Resort, you have to experience dinner at Alati, their signature restaurant. It’s built inside a 400-year-old wine cave, which was the inspiration for the entire resort. We were treated to arguably the best seat in the house. With candlelight flickering on ancient stone, we felt like we’d snuck into a secret society.
I ordered the Astakomakaronada (a lobster pasta dish). The kids devoured their slow-cooked rooster and homemade pasta like it was their last meal. No leftovers = highest possible praise from our crew.
But Penelope’s restaurant in Pyrgos delivered what was one of our favorite meals in all of Greece, especially when you combine the world-class sunset view with the peaceful atmosphere. Compared to visiting Oia the night before, the lack of shoulder-to-shoulder crowds was a welcome change that let us actually relax and enjoy the experience.
We even stumbled upon a local neighborhood concert and dance event at the nearby park when we walked back to our car, and we felt like the only tourists in the entire audience. It was one of those magical moments where you realize you’ve found the authentic Greece that most visitors never see.
Our Favorite Santorini Swimming Spots
Don’t get me wrong, the pool at Vedema Resort is a 10 out of 10. But since we were in Santorini for a few days with 3 boys, we wanted to explore a few other swimming spots.
One day, we made arrangements to check out Istoria Hotel on Perivolos Beach. Gorgeous, quiet, with a private pool steps from the black sand. If you’re on a romantic getaway, it’s perfect as the resort is a small boutique designed primarily with adults in mind who are looking for peaceful luxury.
We also spent some time across the street at their private beach access on Santorini’s famed “Black Sand Beach” and took a quick dip in the frigid waters of the Aegean.
While the black sand was a unique experience, the most unique swimming experience we had in Santorini was at the (not-so-secret) swimming spot at Amoudi Bay, where the boys took turns jumping off the rocks into crystal-clear water.
Technically, there’s a “do not enter” sign on the walking path, but apparently, it’s more of a suggestion, as the walking path was well-traveled and there were dozens of swimmers taking a dip.
I hopped in the water as well, but no rock-jumping for me. If you do decide to hop in for a swim, take a pair of water shoes or hiking sandals as it’s quite rocky below the surface. I will say the reward for taking a swim out into the bay is an unobstructed, postcard-like view of the Oia hillside that makes all the effort worth it.
So if you catch a hot day, I’d highly recommend heading to Oia a little early and having a swim before the sunset.
But honestly, some of my favorite moments in Santorini were the ordinary ones: morning strolls, bakery stops, watching the village wake up. This was Santorini for Greeks, not just tourists.
The One Tourist Thing We Did (And How to Do It Right)
We couldn’t resist Oia.
It’s iconic for a reason. We made a dinner reservation at Kookoo Bar for sunset, braved the parking chaos, and snagged a rooftop table with a killer view. The food was excellent, the sunset was otherworldly, and our only regret was not arriving earlier for those “blue dome” photos before the sun dipped below the horizon.
After dinner, we joined the river of people in Oia’s famous alleys. Beautiful, yes. Overwhelming, definitely. But it made us appreciate the peace of Megalochori all the more.
Here’s something we learned that you can use if you’re driving into Oia for the sunset like we did:
We would have been better off parking at the large lot nearest Ammoudi Bay and then walking up into Oia for the sunset, or in our case, a dinner with sunset view. Yes, it’s an uphill walk but if your legs can handle it, it’s much better than driving back up the hill through swarms of pedestrians in the street and cars parked virtually everywhere.
So whether you plan to swim in the bay or not, your best bet is to come early and find a spot, then hang around for the golden hours of the iconic Oia sunset.
The Bottom Line: Why This “Accident” Was Perfect
What I loved about Santorini is that our kids didn’t need to be “entertained.” They were naturally curious because there was so much to explore. The villages, the food, the music, the history… things that would bore them at home were suddenly fascinating. And Sarah and I? We got the luxury, relaxation, and romance we thought we’d traded in when we became parents.
If you want the Santorini that lives up to the hype, go to Oia – just brace yourself for crowds.
But if you want the Santorini that makes you feel like you’re part of a living, breathing island, set your GPS for Megalochori. It’s not a secret, it’s just not trending on Instagram.
And honestly?
That’s what makes it magic.
Jake Cain is an entrepreneur from Cincinnati, Ohio. He started his journey as a travel writer in 2020 when he and his wife decided to homeschool their 3 boys and embark on a two-year road trip across nearly every US state in their 1999 conversion van. What started as a personal travel blog at SamplingAmerica.com has led to syndication on the AP Wire and MSN.
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