Five Things I Wish I Knew Before Visiting Santorini

Some destinations live in your imagination long before you ever arrive. For me, Santorini was one of them. Yet taking in the view from the cliff-edge in Oia for the first time, far exceeded anything I could ever have imagined. As if the village is suspended between the sea and the sky, Oia stands tall as the jewel in Santorini's crown. Here, high above the sea, white-washed Cycladic properties spill down the side of the Caldera looking out across the bay and blue domed churches cap the landscape. It feels almost other worldly - a place that exists both in reality and somewhere just beyond it.

Having been fortunate to visit the island several times, there are a few things I wish I knew before my first trip:

1. The view is the experience

On my first visit to the island I mistakenly thought that a caldera‑view room was a luxury which would be nice to have, but not essential. Therefore, the first time I stayed in Santorini I did not book a room on the caldera. Yet, I spent the whole trip regretting that decision. Whilst I was able to enjoy the views in restaurants or bars, there is something to be said about having your own corner to take it all in from. In Santorini, the view is the experience. It’s the quiet mornings when the cliffs are washed in soft light. It’s the sunsets that feel almost unreal. It’s the luxury of escaping any crowds and stealing the view all for yourself.

Luckily I've been able to go back to Santorini more than once, and made sure not to make the same mistake again. Staying on the caldera meant that I never missed a moment. I was able to soak it all in on the terrace with a coffee, or a glass of the local Assrytiko wine, and feel completely present. It doesn't matter how many times you have seen the view, its magic re-charges you each time you drink it in. Staying on the caldera makes the difference between seeing Santorini and feeling it, un-rushed. Looking for rooms on the caldera with hot tubs or plunge pools on the balcony is a brilliant way to elevate your experience even further.

2. Where you stay matters more than you think

If it’s your first time, staying in one of the caldera towns — Oia, Imerovigli, or Fira — is key. Oia, especially, is the Santorini you’ve seen in photographs: whitewashed paths, blue domes, and views that don’t feel real. But if you only day‑trip, you’ll see it at its busiest. In summer, the crowds can be a wonder of themselves.

Staying in Oia allows you to slow down, and really feel its magic. One of my favourite times to explore is early in the mornings (up until noon) when the streets are almost empty and the village is slowly waking up. This is the perfect time to get lost in the winding streets, and take your photos from the famous photo-spots without feeling rushed. The evenings offer a different sort of magic. The sunsets, of course, are beyond magical. Yet, when it is dark an ethereal calm sets over the village cast by the twinkling of lights from the properties nestled into the cliff-edge. The lights of the swim-out pools cast a soft shimmer, and in the distance the lights from neighbouring villages dance and sparkle along the cliff-edge. Being able to savour these final hours of the day is a true delight.

If you’ve visited the island before — or if you’re looking for a more serene, alternative experience — the traditional villages of Pyrgos and Megalochori are beautiful options. They offer boutique stays, peaceful streets, and an authentic sense of island life, all without the crowds. Staying in one of these villages feels like discovering a different side of Santorini. Pyrgos benefits from the highest vantage point on the island, meaning that the island unfolds before you as you drink in the views. Whilst the bell-towers of Megalochori and its charming village-square transport you back in time to how the island may have felt before the island became a bucket-list destination.

3. Taxis are expensive — plan accordingly

This was something I didn’t expect. Taxis in Santorini are limited and surprisingly expensive, especially in peak season. If you’re moving between hotels or exploring different parts of the island, the costs add up quickly.

On my last visit to the island, in June 2025, I stayed in two different parts of Santorini. I found it cheaper to hire a car for eight days than to pay for transfers to and from the airport, as well as between the two hotels. It also gave me a lot of freedom to get out and explore more of the island than I had been able to before, which allowed me to really breathe in the experience.

4. It’s the perfect place to start or end an island‑hopping trip

Santorini's airport has great connections to European destinations, which makes it an ideal starting or finishing point for island hopping through the Cyclades. You can fly in, spend a few days settling into island life, and then hop to places like Paros, Naxos, Milos and Mykonos. Or you can end your trip here, letting the Caldera views be your final treat before heading home.

5. Most people stay too little time

Many travellers only stay two or three nights in Santorini — just enough to tick it off the list. But the island deserves so much more time. Allow yourself to experience it slowly. It’s not just about the views; it’s about the feeling of being there.

If you can, stay longer. Consider staying in more than one part of the Island such as Oia and Pyrgos, or mix between the caldera towns and the beaches and beach clubs of Perissa.

Final thoughts: A week is a great amount of time to spend on the Island to truly drink it all in. My favourite place to stay is Oia and it should not be missed on your trip to Santorini.