Last year, after all the training I did to understand the travel industry, I felt ready to take the leap. I decided to organize my first group and try out a small, curated trip. My choice for this first trial? Chania, Crete.
Why Chania?
Crete holds a special place in every Greek’s heart. We grow up admiring its proud and passionate people, learning stories of their hospitality, resilience, and music-filled traditions. Choosing Chania was easy — it’s the most traveler-friendly part of the island and I wanted to explore it at the end of the season, when everything slows down and the authentic side of the island shines through.
Chania surpassed my expectations in every way. The city itself was stunning, the surrounding White Mountains breathtaking, and even the city beaches were amazing. But the real surprise? The food. It was exceptional — even in the most touristic corners. Of course, I had some insider tips from the best Chaniotisa ever, @Maria Bonaki, but even when we picked restaurants at random, we experienced incredible quality and warmth.
Why Travel in Late September or Spring
From experience, the best time to visit popular Greek islands is late September or even October. The sea is still warm, the crowds are gone, the weather is mild, and the atmosphere is relaxed. You feel like a guest, not a tourist.
Spring is also a beautiful time to go. The sea might be a bit cool for swimming, but the land is in full bloom, perfect for mountain walks, herb collecting, and enjoying the local cuisine at its freshest.
Exploring Crete’s Rich History
We visited Knossos and the Heraklion Archaeological Museum — both pleasantly busy. We had space to enjoy the exhibits and absorb the stories from our guide. Walking through the ruins and hearing about Europe’s first civilization was a real moment of connection with the ancient world.
Nature
We also hiked Samaria Gorge — one of the most challenging and rewarding experiences I’ve ever had. I didn’t expect it to be so physically demanding (my knees were not prepared!), but the beauty and feeling of accomplishment made it all worth it. At the end of the hike, we reached Agia Roumeli, a peaceful village that you can only get to on foot or by boat. While we waited for the ferry, we relaxed with good food and a view of the Libyan Sea.
Elafonisi: A Dreamlike Escape
Of course, we couldn’t miss Elafonisi, and it absolutely lived up to its reputation as one of the most beautiful beaches in the world. It’s hard to describe — even photos don’t do it justice. Think pink sand, shallow turquoise waters, and a small island you can walk to through warm water no more than 1.5 feet deep. Since it was the off-season, we had no problem finding sunbeds or enjoying the quiet beauty of the place.
The Spirit of Cretan Resilience — and a Truly Local Experience
When I was preparing this trip, I connected with Eleni from Balos Travel, who also runs a beautiful Cretan cooking workshop. One afternoon, we joined her at her family’s home, where we cooked together with her mother and her granddaughter — three generations of Cretan women, all sharing their kitchen and their stories with us.
As we chopped, stirred, and laughed, Eleni talked to us about Cretan resilience — how every family, no matter their circumstances, produces their own wine and olive oil, grows their herbs, and keeps close ties to the land. It’s a way of life deeply rooted in strength, pride, and love of place.
Evenings in the Old Town
Our favorite part of every evening was wandering through the Old Town of Chania. We ate at local tavernas, had drinks by the harbor, and shopped from small artisan shops selling handmade jewelry, traditional knives, and clothing — each with a story behind it. The atmosphere was relaxed, friendly, and full of life.
I’m Going Back — And You Can Join Me
This was my first attempt at leading a group trip — and it was a success in every way. The people, the experiences, the connection to the place — it reminded me why I want to do this. That’s why I’m going back this September 2025, with a new group and an even more carefully curated itinerary.
If you’re someone who loves culture, food, music, local connection, and seeing Greece beyond the postcard, this trip is for you.
Want to come? Stay tuned — I’ll be sharing more soon.
2 responses to “Chania in September: My First Group Trip and Why I’m Going Back”
Hey there. Would love to hear details times Cost ecc
Lisa
I will happily send to you! It will be great if you can come with me!