Santorini in May: Our Eight-Day Escape Together

We stayed at Mare Nostrum Santo, a family-run property outside Oia, and absolutely loved it. What I remember most is how welcome we felt.

When our hire car had not yet arrived, the people at our accommodation drove us into Oia and collected us again, without charging us. It was such a thoughtful thing to do, and it set the tone for the stay. There was always time for a chat if we fancied one.

Breakfast was included in our booking. Each morning began with coffee and a lovely fresh breakfast before we headed out to explore. Those simple mornings are among my happiest memories of the trip.

For our way of travelling — a comfortable base, a car and plenty of time to discover the island — it was a wonderful choice. It is outside Oia itself, so factor transport into your plans rather than expecting to step straight into the village.

If your version of Santorini includes a particularly special hotel, these three places deserve a look. Think beautiful settings, time to linger and a stay that becomes part of the holiday itself.

An elegant choice for a luxury stay in Oia, with Cycladic architecture and the island’s spectacular setting at the heart of the experience. Put this on your shortlist if the hotel is going to be one of the main treats of your trip.

Set above Ammoudi, Canaves Epitome brings a different look to the island’s luxury hotels, with volcanic stone, generous outdoor spaces and sea and sunset views. A lovely option to consider if you want your hotel time to feel unhurried.

In Oia, overlooking the caldera and the Aegean, Andronis Luxury Suites is a strong contender for a special trip together. Browse the individual suites carefully to choose the outdoor space and facilities that suit the holiday you have in mind.

May felt just right for us. The weather during our stay was already lovely, and we could enjoy the island before the busier part of the season took hold.

That timing mattered. For me, much of Santorini’s appeal is being able to enjoy the views and the atmosphere without feeling hurried or squeezed into a crowd. I would choose my dates carefully for another visit, because a busy little street can feel very different when everyone wants to be in the same place.

I would happily return in May, based on our experience. I would not treat the month as a guarantee of empty streets or uninterrupted sunshine, though: our holiday is a memory of one particular visit, rather than a promise of what every May will be like.

Oia, Imerovigli, Kamari and Paradisos Beach are our four recommendations not to skip. Here is why each earned its place.

Oia is one of our absolute recommendations. The white buildings, blue domes and views across the water are a huge part of what made us fall for Santorini in the first place.

Our photographs are full of those colours, but some of my favourites include the smaller moments: coffee with a view, something to eat, and the two of us together with that wonderful backdrop.

I would give Oia time in your plans. See the views you came for, then leave room to sit down and enjoy being there. That is the version of a holiday I want to remember.

Imerovigli belongs on our list alongside Oia. We explored the island throughout the week, and it is one of the places I would tell someone visiting for the first time not to miss.

You do not need to choose only one famous village and call it done. Part of the pleasure of having eight days was being able to see different parts of Santorini without making the whole trip about one stop.

Kamari is another of our firm recommendations. A Santorini holiday can easily become all about the white villages and their views, but we loved making space for the beach side of the island too.

If you are planning a longer stay, I would keep some of your time for the coast. For us, exploring and relaxing by the water belonged in the same holiday.

Paradisos Beach, also known as Paradise Beach, is in the north of Santorini, in the Baxedes area near Oia. It was our recommendation for a quieter beach stop: a little out of the way, peaceful, and with shallow water where we spent our time.

That is how we experienced it during our visit. Conditions can change with the wind, so take the day as you find it rather than expecting the water always to be calm.

Of all the places in this guide, this is the one I would point you towards when you feel like a simpler afternoon by the sea.

Once our car arrived, we spent the week exploring the island. We visited the well-known places, fitted in wine tasting, and had the freedom to make different kinds of days out of the trip.

For us, having a car made sense with our accommodation outside Oia and the amount we wanted to see. It meant our holiday could include villages, quieter beach stops and beach clubs, rather than keeping us in one area.

That does not mean everyone needs to drive. Think about where you will stay and how much you want to move around before choosing your transport. If you do hire a car, check the collection arrangements, insurance and parking at your accommodation before booking.

If there is one experience I would make room for again, it is an evening on the water.

Bas and I often book a boat trip when we are staying on an island or near the sea. It has become one of our favourite things to do together. Even when the sunset does not put on its best show, we usually have such a lovely time that the trip is worth it anyway.

Santorini gave us a spectacular one. Our cruise included a barbecue, and the sunset was breathtaking. Looking back at those photographs takes me straight back to that evening.

For your own trip, look for a sunset sailing with a barbecue or meal included. Check the boat type, group size, departure point and transfer arrangements so you choose the kind of evening you actually want.

The current option below is a starting point for planning a similar experience; it is not a record of the operator we booked in 2018.

Wine tasting was part of our week too, and it gave us another way to experience Santorini beyond the villages and beaches.

If you would like to include it in your own plans, a wine tour with transfers can make the day easier to organise. Check which wineries are included, how many stops there are and whether the tasting style suits you.

One of our photographs also shows Santorini Brewing Company, with its distinctive donkey signs. It is a lovely reminder that there were smaller discoveries throughout the week, as well as the places everyone recognises.

We love trying beach clubs when we travel. A comfortable place to settle, something to drink and a few hours by the water are very much our kind of holiday.

Wet Stories was one of the places we visited. It is on Perivolos Beach, so it gives you another coastal stop to consider alongside Kamari and the quieter north. Check its current seasonal opening and reservation arrangements when planning a visit.

One practical thing I would absolutely pack for Santorini is water shoes. The dark, grainy beach material reminded me of poppy seeds, and it was quite different from the soft, pale sand people sometimes picture when they think of a beach holiday.

Santorini does have sandy beaches, including black-sand stretches, as well as pebbly and rocky shores. My advice comes from the places we visited: choose your beach with that landscape in mind, and bring footwear that makes getting into the water more comfortable.

For all the lovely views, one of my clearest food memories is a pita gyros from Pitogyros in Oia. It was the best I have ever eaten, and it is exactly the sort of meal I would want to find again on a return trip.

That balance is part of what made Santorini so good for us. There were beautiful settings and memorable evenings, but also simple food that we absolutely loved. A holiday does not need every meal to be an occasion for it to stay with you.

For us, absolutely. Eight days gave us time to explore and still have a holiday. We could visit the places we wanted to see, enjoy the beach, go wine tasting and spend an evening on a boat without turning every day into a checklist.

I would not say every visitor needs the same length of stay. But if you like the combination we do — exploring, beach clubs, good food and time together — there is something wonderful about giving the island more than a fleeting visit.

Santorini remains one of our favourite trips as a couple. I would happily go back, choose my dates thoughtfully, and make space for those lovely ordinary moments between the big views.