A Romantic Escape Based in Imerovigli
Three days in Santorini may not sound like very long, but for a honeymoon I think they can be just enough — provided you resist the temptation to fill every available hour.
Santorini has a way of making people feel that they must see everything: Oia, wineries, beaches, archaeological sites, sailing trips, sunsets from several different angles. You could certainly try to fit them all in, but you might come home needing another holiday.
I would rather choose a few things that are genuinely worth experiencing, organise the days sensibly so that you are not constantly driving backwards and forwards across the island, and leave some time in between simply to enjoy being here.
If you are staying in Imerovigli, you already have a very good place to begin.
Here is how I would spend three days.
Day 1 — Arrive, Settle In and Stay Close to Home
However many photographs of Santorini you have seen before you arrive, the first real view of the caldera is still difficult to prepare for. So I wouldn’t plan very much for your first afternoon.
Once you have settled into your house, give yourselves some time to enjoy being there. Sit outside, have something cold to drink and, if you still have some energy after the journey, take a walk around Imerovigli. You don’t need a particular route. The village is small enough to wander through, and some of its nicest views appear unexpectedly between houses, churches and narrow paths.
For your first evening, stay close to home. For most of the season, you can watch the sun disappear from the house. Around the height of summer — roughly from 10 June to 10 August — the sun itself sets just outside the direct view from our terraces. You will still see the changing colours across the caldera, but if you want to watch the sun reach the horizon, it only takes a few steps around the corner.
After sunset, you can continue the evening on foot. The caldera path leads from Imerovigli through Firostefani and on to Fira, so choose a restaurant somewhere along the way depending on how far you feel like walking. Firostefani has plenty of good options close by, while Fira is the better choice if you want a little more life after dinner.
There is really no need to do anything more on your first day. You have just arrived in Santorini, and tomorrow there will be plenty of time to explore.
Day 2 — Oia, Ammoudi and Skaros, in Either Direction
For your second day, I would combine Oia, Ammoudi and Skaros. They fit together naturally, but the order depends very much on what kind of people you are — and, more specifically, on how you feel about getting up at dawn while on honeymoon.
If You Are Early Risers
If an early start doesn’t bother you, go to Skaros first.
In summer, this is one of the best times to walk there. The path is exposed and there is very little shade, so setting out before the heat builds makes the walk considerably more enjoyable. Imerovigli is also particularly peaceful at this hour, and the early light over the caldera is beautiful.
There is no need to turn it into a serious hike. Walk as far as you feel comfortable, enjoy the views and come back to the house in time for breakfast. Since breakfast is served between nine and eleven, you can still take your time over coffee afterwards.
Later in the morning, head to Oia. You will have a chance to explore the village before the late-afternoon sunset crowds arrive, wandering through the smaller streets and stopping whenever something catches your eye before eventually making your way down towards Ammoudi.
Bring your swimsuits with you. Beyond the harbour, a short but slightly tricky path along the rocks leads to a swimming spot inside the caldera, beneath the cliffs of Oia. It is well worth the effort, but come prepared: wear sturdy shoes, carry as little as possible and don’t expect a beach, sunbeds or facilities when you get there. It is simply a rocky corner of the caldera with deep, clear water and a spectacular view — which is precisely what makes it so special.
After your swim, return to Ammoudi for lunch by the water and take the afternoon slowly.
One practical thing worth knowing is that getting down to Ammoudi is considerably easier than getting back up. The steps are substantial and, in summer, the climb can be particularly tiring in the heat. Arranging transport for the return is a perfectly sensible option.
If you have always wanted to see the famous Oia sunset, however, I would stay in the area for the evening rather than leave and come back later. Reserve a table well in advance at a restaurant with a sunset view and make dinner part of the experience. Oia at sunset is busy — there is no getting around that — but having somewhere to sit makes the whole thing considerably more civilised.
If Dawn Is Not Part of Your Honeymoon Plans
Simply reverse the day.
Go to Oia in the morning, when it is easier to enjoy the village before the main afternoon crowds arrive. From there, continue to Ammoudi for your swim and lunch, then return to Imerovigli for a few quiet hours at the house.
This is exactly the kind of gap I would deliberately leave in a three-day itinerary. Have a shower, sleep for a while or sit outside and do very little before going anywhere again.
Later, once the temperature has dropped, walk towards Skaros. Take water, wear sensible shoes and don’t feel that reaching the top is compulsory. The route itself, and the views along it, are enough to make the walk worthwhile.
Stay for the evening light and sunset before walking back to Imerovigli for dinner.
Both versions cover essentially the same part of the island. The difference is whether you would rather have Skaros at its quietest in the early morning and experience sunset in Oia, or enjoy Oia earlier in the day and save the quieter sunset for Skaros.
Day 3 — Pyrgos, Santorini Wine and the South
For your third day, I would head south and stay there. This is particularly convenient if you have booked an afternoon catamaran cruise, as most of them leave from Vlychada. Rather than spending part of the day driving back and forth across the island, you can make your way gradually south and finish at the marina.
If you have a rental car, take your swimsuits and everything you will need for the boat with you in the morning. There should be no reason to return to Imerovigli before the cruise.
After breakfast, start with Pyrgos. The old village climbs towards its Kasteli, the fortified settlement at the top, through narrow passages, old houses and churches. It feels quite different from the caldera villages you will already have seen, and you don’t need to spend hours there to get a sense of it. Take a walk through the old part of the village and then continue south.
Stop for Santorini Wine
This is also a good day for a winery visit. Two places I particularly like are Santo Wines and Venetsanos Winery. Both overlook the caldera and fit naturally into this route, but they offer slightly different experiences.
Santo Wines is the local agricultural cooperative, so a visit gives you an introduction to more than the island’s wine. You can also discover some of the products Santorini has traditionally produced, including its famous fava and capers, olive oil and other local products. If you like taking something edible home from your travels, it is a particularly good place to look.
Venetsanos is one of Santorini’s historic wineries, built into the cliff above the caldera, and its unusual architecture is part of the experience. The winery was designed around the practical difficulties of producing wine on the steep landscape, so there is an interesting story behind what you see as well as what you taste.
Both are excellent choices, so I would simply choose whichever appeals to you more.
Whichever you visit, have something to eat with the tasting. Apart from being sensible in general, you are going sailing later in the afternoon, and several glasses of Santorini wine on an empty stomach are probably not the ideal preparation.
Continue Towards Akrotiri
From there, continue towards Akrotiri.
If history interests you, visit the prehistoric settlement, one of the island’s most important archaeological sites and a fascinating glimpse of Santorini long before white houses and honeymoon photographs became part of its story.
If archaeology is not particularly your thing, continue towards the lighthouse at the southwestern end of the island for the views, or use the time for a swim.
Vlychada is my choice if you want to see one of Santorini’s most unusual landscapes. Its pale volcanic cliffs have been sculpted by wind and time into extraordinary shapes, and the beach feels completely different from the caldera side of the island.
Don’t try to fit the archaeological site, the lighthouse and the beach into the same few hours. Choose according to what interests you, how hot the day is and how much time you have before the cruise. You are heading towards Vlychada anyway.
Finish the Day at Sea
Most afternoon catamaran cruises leave from Vlychada at around four, which is why organising the day geographically makes so much sense.
If you have your own or a rental car, I recommend going directly to the marina. The cruise companies offer shared transfers, which are useful if you don’t have transport, but collection can begin around an hour before departure and sometimes takes a while as guests are picked up from different properties around the island. Going directly to Vlychada is usually quicker and gives you more control over the day.
Once the boat leaves, there is nothing else you need to organise. Most cruises include swimming stops, food and drinks, and seeing Santorini from the water gives you a completely different sense of the island. Looking back at the cliffs from inside the caldera is also one of the best ways to understand their extraordinary scale.
By sunset, you will have spent the day moving gradually from the villages and vineyards of the interior towards the southern coast, and finally out onto the water. It is a very good way to spend your last full day.
Your Last Evening in Imerovigli
By the time you return from the cruise, I wouldn’t make another dinner reservation. You will have eaten on the boat and, after a full day out, coming back to your house will probably be enough.
Have a late drink outside or, if your house has a jacuzzi, make use of it.
Over three days, this itinerary takes you through Imerovigli, Firostefani and Fira, north to Oia and Ammoudi, and south through Pyrgos towards Akrotiri and Vlychada. You will see some of the places everyone comes to Santorini hoping to see, but also several very different sides of the island.
More importantly, you won’t spend your honeymoon moving from one appointment to the next.
It is very easy to arrive in Santorini with so many recommendations that a three-day holiday becomes a list of things you are afraid to miss. There will always be another beach, another winery, another village and another restaurant someone insists you absolutely have to visit.
Three days are enough to see a great deal of Santorini, but not all of it — and I don’t think you should try.
See the places that genuinely interest you, organise your days so that getting from one to the next makes sense, and leave enough time for breakfast to last longer than expected, for an afternoon on the terrace, or simply for changing your plans because you are perfectly happy where you are.