Peloponnese to Paros: A Family Adventure, Rooted in Discovery

Greece was where I spent my 20th birthday, then my 30th, so when 40 came around, it was really the only place I wanted to be. Yes, it’s far from Toronto, and yes, getting to the places we wanted to go was more complicated than a lot of other options. But like New York and Paris, Greece has always had a very special place in my heart. I was a little nervous about returning to islands I’d loved 10 and 20 years ago, especially now traveling with a 5- and 7-year-old and all the things that come with that: separate sleeping spaces, a pool, a restaurant on site if possible, toting shovels and umbrellas around, etc. Times had changed since late nights in Mykonos and seeing six islands in 10 days, and I was here for it.

Our first stop was Salanti, a tiny town in the Peloponnese that felt blissfully remote in the best possible way. We rented a house on a quiet beach—i.e., we saw no other humans—and it was exactly the reset we wanted, and such a lovely base for exploring a part of Greece I’d never been to before. Day trips to Hydra, Porto Heli, Nafplio, and Spetses were easy. I completely fell for Hydra. It’s not the easiest with small kids given there are no cars and a lot of walking, but it was so beautiful and distinctive that I already know we’ll be back when they’re older. We rented a boat from Porto Heli, ate at local tavernas by the sea, and leaned into the quieter, slower side of Greece.

From there, we spent a night in Athens at Ergon House, which was ideal for a quick stop. The family room really worked for us, the location was incredibly central, and the market downstairs was such a win with kids. They also put together to-go breakfast boxes for our early ferry, which felt like one of those small but crucial travel details that makes all the difference.

Then came Sifnos, and, as a foodie, I was absolutely blown away. I knew it had a reputation, but it still exceeded every expectation. The island is small, relatively undeveloped, and full of character and charm. We stayed at Verina Terra, and having a pool, warm service, and the beach town within walking distance made it such a memorable place to wake up on my 40th birthday. Omega 3, Pelicanos, and Loggia Wine Bar are on every list, yes, but completely deservedly so.

Paros was our last stop, and I went in a little wary that it might feel too crowded or too polished by now. Instead, I was so pleasantly surprised. The beaches were beautiful, the restaurant scene still had so much character, and Antiparos and the caves were a huge hit with the kids. We had dinner and drinks at The Rooster, and they could not have been more welcoming or accommodating with children, which never goes unnoticed. We stayed at Acron Villas, which was perfect for a family: an incredible view, a huge pool, genuinely helpful staff, and a kitchen that became very important after long days when the kids had absolutely no interest in one more pita.

Greece is magical, full stop, but seeing it through my kids’ eyes made me love it even more.

For more inspiration and insider recommendations, visit our Greece page.