48 Hours in Santorini: How to Do It Right
Santorini is one of those places that looks exactly like the photos and somehow still manages to exceed them. It is also a destination that punishes bad planning. Two days is enough time to do it well, but the way you structure it makes all the difference.
We had private airport transfers on both ends, a private day tour through the wineries and villages, and a hotel I had been wanting to stay at for years. Here is exactly how it came together.
Where to Stay
Andronis Boutique Hotel, Oia, Santorini
Andronis Boutique Hotel sits right on the caldera edge in Oia. The suites are carved into the cliffside in traditional Cycladic style, all white-washed curves, natural stone, and organic-shaped walls. Minimalist without being cold. The private jacuzzi on the terrace faces the Aegean, and the infinity pool dissolves into the same view.
It is a small property, which works entirely in its favor. Service is personal in a way that larger hotels just cannot replicate. Breakfast is worth sitting down for every morning.
What We Did
Private Airport Transfers
Santorini Airport is small and the transfer situation ranges from organized to chaotic depending on when you land. Having a private driver waiting the moment we walked out set the right tone immediately. No shared shuttles, no hunting for a taxi. We were in the car and heading to Oia within minutes.
Private Island Day Tour: Wineries and Villages
I always tell clients to go private in Santorini and I follow my own advice. The roads are narrow, parking is a real problem, and navigating efficiently between stops requires someone who knows the island. The flexibility to linger where you want and move on when you are ready is worth it every time.
Our first winery stop of the day. The production side is genuinely interesting, and Santorini wine has a story worth understanding: the volcanic terroir, the basket-trained vines known as kouloures, the intense Assyrtiko grape. As a tasting experience though, it did not fully deliver for me. The setting and curation were not quite there. Worth a stop if you want to see the production process up close and a combined art gallery, but not my top recommendation.
Santo Wines
Santo Wines in Pyrgos is the island’s cooperative winery, built on five levels into the hillside above the caldera. The terrace view alone justifies the visit. The Assyrtiko is crisp and mineral, immediately recognizable as Santorini. The Vinsanto dessert wine is worth ordering on its own. The snack pairings, local cheeses and dried tomatoes, are genuinely good.
Book a late afternoon slot if you can. Watching the light shift over the volcano from that terrace with a glass of white wine in hand is one of those moments you will keep coming back to.
Imerovigli
Imerovigli sits at the highest point of the caldera rim and has arguably the best panoramic views on the island. Quieter than Oia, more residential in feel, and the souvenir shopping is more curated. Local ceramics, hand-painted tiles, small food producers selling capers and fava. Worth the slow walk.
Megalochori
This is the stop most visitors miss because it does not have a famous sunset attached to it. One of the best-preserved traditional villages on the island, with narrow Cycladic alleyways, barrel-vaulted wine cellars built into the hillside, and a central square that has been there for centuries. The shopping here is smaller scale and more local. We stayed longer than planned and left with a few good finds.
Where We Ate
Souvlaki n’ Wrap, Oia, Santorini 847 02, Phone: +30 2286 072448
In Oia, where every restaurant with a caldera view charges accordingly, Souvlaki n’ Wrap is the reality check you did not know you needed. Fresh pork gyros, kebab, falafel, all made to order and priced under 10 euros. We grabbed lunch here between exploring the village and it was honestly one of the best bites of the trip. The kind of spot locals eat at while tourists line up elsewhere for a view.
Paradox Thai Food and Bar, Oia, Santorini 847 02, Phone: +30 2286 071675, Hours: Daily 1pm to 11pm
Not what you expect to find in Oia, and that is exactly the point. Paradox is a casual Thai and Asian restaurant near the Oia bus stop, away from the main tourist corridor, and pleasantly good in a way that surprised us. When you have been eating Greek food for days straight, a solid bowl of curry or a plate of pad thai lands differently. Affordable by Santorini standards, friendly staff, and a nice change of pace.
Mia’s Restaurant, Fira-Oia Regional Road, Oia, Santorini 847 02. Phone: +30 2286 072072, Hours: Monday 5:30pm to midnight, Tuesday to Sunday 12:30pm to midnight
Mia’s is where we went for a sunset dinner. Could be a bit windy upstairs, but their indoors dining can be worthwhile as well. Set in a Cycladic residence on the caldera edge in Oia, the kitchen focuses on traditional Greek flavors with a modern approach. Fresh fish, local cheeses, vegetables sourced from Cycladic farms. The setting is beautiful without being overdone and the food is the kind that makes you slow down and pay attention. I did not care for their bread (9 euros and was not served warm) but their cocktails were killer. Reserve in advance and time it for the light.
Savvas Popeye, Agios Georgios Beach, Perivolos, Santorini 847 03, Phone: +30 2286 081332, Hours: Noon to 11 pm daily, early May through mid-October
Savvas Popeye sits across from the black sand beach at Agios Georgios, just south of Perissa. The restaurant has been on this stretch of coast since 1956, and that longevity tells you something. The fish comes in daily on the family’s own boat. You pick from the fresh catch display, it gets weighed, you get a price, and it comes back grilled simply and correctly.
Order the tomato fritters. They are one of the definitive bites of Santorini: the local cherry tomatoes are sweeter and more concentrated than anything you will find off the island, and the fritters are made properly here. The octopus is excellent. Greek salad with local capers. House white wine. A long and easy lunch with the black sand right in front of you.
If you are used to Oia’s caldera-view restaurants, this will feel like a different island. It is, and that contrast is part of what makes Santorini feel complete.
One More Thing: Go in May or September
If your dates are flexible, this matters more than most people realize. July and August in Santorini mean cruise ships unloading thousands of people daily into Oia, hour-long waits at restaurants that were not worth waiting an hour for, and sunset crowds at the castle that make it nearly impossible to enjoy the moment you came for.
May and September are a different island. The weather is warm and the restaurants are actually reachable without a reservation made weeks out, and the villages feel like places rather than queues. You will get better service, better tables, and a version of Santorini that is closer to why everyone wants to go in the first place. Book the shoulder season and you will not think twice about it.
Plan Your Trip
If you are thinking about putting together a Santorini itinerary, Nomoon Travel can take care of it from transfers to day tours to hotel bookings.
