How to Plan Your Santorini Itinerary
There’s no denying that Santorini is one of the most beautiful places in Greece. I'd bet that hundreds of dreamy photos have landed this island on your must-see list. The problem with Santorini is that it’s as popular as it is stunning. You’ll find Oía crowded even in the off season, and what’s local is often blended right into the tourism that the island thrives on.
Here’s my solution: an itinerary formula to skip the crowds and theme park vibes, and spend your days enjoying the best parts of Santorini. Take this formula and tease it out for a long, lazy honeymoon (a dream!) or wrap it into a couple days and island hop your way through Greece.
Getting to Santorini
September is an ideal time to visit: the sea is still warm from summer, but some of the crowds are gone for the season. After you find the best tickets for your transatlantic flight, book the short trip out to Santorini (stick to Olympic or Aegean airlines).
There are no shortage of luxury hotels in Oía, and this is place to splurge on somewhere with a panoramic view (isn’t that why you’re here?) and an enviable pool situation. I stayed at both Kirini by Katikies and the equally wonderful Canaves Oia Hotel.
Like Italy, Greece has a pretty relaxed attitude about details like public transit schedules and store hours. Do you love that for being delightfully un-American or hate that it’s unreliable? You might be able to grab a taxi at the airport, but there often aren’t enough to go around. And after many hours of travel, you don't want to drag luggage onto a bus and through town. Instead, arrange transportation through your hotel before you arrive on the island.
Mornings in Oía
Wake up before sunrise to have Oía almost entirely to yourself. Without the crowds, you’ll feel less like you’re in a mediterranean Epcot and more like you’ve stumbled into a real-life storybook village. Shops won’t open for a while, and day trippers won’t arrive until they do, so take your time.
Walking down the main road, turn off to the left every chance you get. These side streets lead to some of the best views of the blue domed rooftops (there are only a handful!) and of the island itself. Head up to the Byzantine castle ruins for the view, and count all the cats you see along the way. Wander through the streets and stairways until you loop back to something familiar. When people start to trickle into town, head into a restaurant or back to your hotel for a long breakfast.
Afternoons in Santorini
Oía will be busy in the afternoon, so it’s time to choose your own adventure:
Lounge at the hotel’s pool, alternate between sunning and swimming. You know the drill.
Take a taxi to Fira for lunch, then hike the famous 3-hour trail back to Oía- or just 30 minutes to Imerovigli.
Grab your beach bag and follow the steps down from Oía to Amoudi Bay. Have lunch at one of the restaurants along the water, then make the short hike to St. Nicholas rock to swim and watch the cliff jumpers.
Shops selling souvenirs, local crafts, and clothes line the streets in Oía - sneak into town to shop while everyone’s eating lunch. You can’t miss Atlantis Books, and Cave Spilia has the perfect Greek leather sandals. Stop in at Pito Gyros for a quick lunch, and Lolita's Gelato for dessert.
Make your way to the other side of the island, and visit Perissa's black sand beach.
Book a private catamaran for the afternoon, and stay out in the Caldera until sunset - I wish I had time for this on my trip!
Where to watch the Sunset
Santorini’s sunsets are famous, and literal busloads of people will fill Oía to catch a glimpse. Rather than flocking to the most popular viewpoints, try one of these:
Out on a private catamaran or a sunset cruise, you'll have one of the best views of all. This isn’t cheap and requires some advance planning, but it’s the one thing still I wish I could have done while I was there!
Skip it. Even if you don’t have a direct view of the sunset, that wonderful golden-hour light is everywhere. And while everyone’s chasing west-facing views, they’re leaving behind plenty of wonderful spots to enjoy the evening. So have dinner on your balcony, or cocktails by the pool. Do some local wine research at Oía Vineyart, or book a table at Black Rock.
‘star’ the map below to access it from the google maps app on your phone.
Santorini Packing List:
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