For your first visit 2 days is enough to get well acquainted with the island.
Distances between main destinations are longer than one might expect. A mode of transportation is necessary to see multiple villages.
Worthy destinations: Oia; Pyrgos; Imerovigli; Acrotiri Archaeological Site.
Left for another visit: Fira; Megalochori.
Last visit: July 2018.
Santorini (officially in Greek, Θήρα – Thira) is among the most-desired destinations for a large segment of casual travelers. Its blue-domed churches, frequently seen on the pages of travel magazines, exert a significant pull on a large number of people. Those who come invariably appreciate, in addition to churches, the remarkable volcanic caldera, the distinct boxy-with-rounded-roof white-dominated architecture, and the impressive and comparatively barren landscape.
They also have to deal during the high season with such significant crowds that it diminishes the appreciation.
Nowhere that is more obvious than in Oia ♥♥♥, a picture-perfect labyrinth of narrow walkways full of galleries and shops (jewelry is the prevalent product on offer, but there is also plenty of clothing stores, plus a very popular bookshop). Every corner of Oia is incredibly picturesque. There are many beautiful vistas. But the central streets and points of interest get too crowded by late morning – and stay crowded through the day.
Sunset viewing in Oia – a nearly “must” activity – is simply insane. The westernmost part of the village comes to a standstill with hundreds of people hanging on for the sun to disappear; best positions are being occupied hours in advance. If you have a sunset view from the terrace of your hotel or apartment, you are well advised to use that. Otherwise, book a restaurant with west-facing terrace and give yourself ample time to get there even if it feels that you only need 5 minutes.
There are several minor points of interest in Oia, but neither Maritime Museum nor Oia Museum were open strictly according to posted hours – we found them open only at the times that we were not willing to spend on them. We also did not have the energy to go down (and later up) to Ammoudi Bay (which is not really a point of interest, but rather a location for a couple of popular restaurants).
The ruins of Byzantine castle are worth a quick stop, for the views.
Although Santorini is not a big island, you need a mode of transportation to get to villages other than the one you are based at. There are car services, and you can rent a car to drive yourself. More fun activity is renting ATVs ♥ – there are many agencies offering them, and you don’t have to reserve far in advance. You can then get around the island pretty easily on your own, but it is not without drawbacks: cars get impatient with slower ATVs, which makes driving occasionally hazardous; the vehicles themselves are fairly easy to handle, but can present challenges to some; we personally had bad luck with one of the vehicles dying on us during the ride, which took some shine off. Keep in mind that you will be constantly in the sun – wear a lot of sunscreen, and reapply frequently!
You can also arrange for a guided tour of the island. We highly recommend Chara Abelioti ♥♥♥ (TripAdvisor link) who gave us a fantastic overview of what the island has to offer, bringing us to villages, local shops, majestic viewpoints, and engaging parents and kids every minute of every hour we spent together.
Pyrgos ♥♥ (full name is Pyrgos Kallistis – Πύργος Καλλίστης) is a picturesque village that is nowhere as crowded as Oia. Climb up to its top for views and look into its churches.
Akrotiri archaeological site ♥♥♥ (Ακρωτήρι) is an impressive enclosed excavation of an ancient town, with whole buildings and many artifacts well-preserved. Our appreciation of it was greatly enhanced by Chara’s narration and usage of slides on a tablet, so consider visiting the place with a guide.
Faros Market ♥, close to the south-western tip of the island, is a great stop to try local wines and produce. You can also visit local wineries, which we did not fit into our schedule beyond a quick stop to admire the grapevine “baskets”.
Imerovigli ♥ (Ημεροβίγλι) is another pleasant village, although possibly not as picturesque as Pyrgos. It has unparalleled caldera vistas, though, and Skaros Rock is a superbly scenic spot if you choose to walk to it (we only looked at it from a café terrace).
We did not get to explore the main town of the island, Thira (or Thera, Θήρα – sometimes written in English as Fira), on account of the aforementioned ATV mechanical problem. There are a couple of museums, Archaeological Museum of Thera and Museum of Prehistoric Thira, that may be worth visiting, as well as the Orthodox Metropolitan Cathedral, plus a couple of other churches.
The village of Megalochori (Μεγαλοχώρι) is another likely destination that we bypassed on our visit.
Santorini is not known for many good beaches – the best ones are on the southern coast of the island. The closest to Oia is Katharos Beach, which still requires driving to and is not very good – rocky and rough.
We did go to Perissa Beach ♥♥ during our guided tour – it is one of the best on the island. The ground is small black pebble and sand, including the sea floor; waters are calm and warm; lounge chairs and sun umbrellas are paid for by ordering drinks from the nearest café.
If you decide to leave Santorini on a ferry, please be prepared that your last impression of the island will be barely organized chaos. The narrow set-up of the port causes congestion, and makes getting on a ferry a quite trying exercise. The only positive is a bunch of cafés to bide your time in.
Places to Eat
All of our meals on Santorini in 2018 have been in Oia.
Elinikon ♥♥ – a relatively small café at the western edge of the village. Great meze menu, as well as salads and main courses; all of our selections were great. Very friendly service. Damage: €72 for 4, with wine and tips.
Kyprida ♥♥ – an upper-terrace restaurant in the Maritime Museum vicinity. Extensive menu, good-to-great food, especially the fresh fish of the day. Excellent sunset views when correct tables are reserved in advance. Nice and friendly service. Damage: €110 for 3, with wine and tips.
Strogoli ♥ – also an upper-level terrace close to the Maritime Museum. On the more expensive side even for Santorini. Everything we ordered was of excellent quality. The service was very efficient until it was time for desserts, which inexplicably took very long to be brought out. Damage: €150 for 4, including tips.
Skala ♥ – on the main street towards the village center. Very nice service, good setting with the view over caldera (no sunset), excellent menu, great choices all over. Damage: €75 for 2, with wine and tips.
Vitrin ♥ – near the castle ruins. Great for breakfast, large selection of crêpes, two levels of seating, very nice experience. We ate here twice, paying no more than €25 for 4 people (but with a 20% discount provided by our accommodations).
Lounge and meze bar Katharos sits above the beach of the same name that is the closest to Oia. You need some form of transport to get here, even though it is technically only 15-20 minutes walk away from the village. There are plenty of choices on the menu, but a couple of items that we selected were not to our taste. The setting is pretty nice, and the service is friendly if slightly detached. Damage: €72 for 4, with wine and tips.
Café Lioyerma ♥ at the western tip of the village has a pool, which is a big hit with the children. You can technically use it even without ordering anything (especially since the service here is fairly aloof), but ordering a single drink definitely entitles everyone in your party to swimming.
Lodging
In 2018, we stayed at the AirBnB-listed Santoimage House ♥ (link). Close to the western edge of Oia, it is a traditional cave-like half-basement apartment. Most necessities were covered, but the apartment was not stocked with much beyond water and a bottle of wine. The street-level terrace is both a great people-watching opportunity and a little awkward because it provides no privacy, but you can get partial views of sunset there. Netflix-enabled TV was a huge plus for kids. Among drawbacks: one low entrance door (two people banged heads three times in the first day; there is a taller second door, but somehow its lock only opened from the inside, making it a bit impractical as a main entrance); there is only a single full bathroom, which presents challenges to a party of 4; shower stall does not have a fixed head, only hand-held; second bedroom is only accessible through the master; the third bed is a mini-loft in the inner bedroom, a bit dangerous with a possibility of falling down at night. All considered, a positive experience!