A Greek island is about as close to heaven as my inner traveler can imagine. So after 5 amazing days on the mainland, my boyfriend and I continue our 2-week Greece trip with an island getaway in the Cyclades. First on our itinerary is 4 days in Santorini, and I can’t wait for Aegean paradise.

4 Days in Santorini

4 Days in Santorini

Waving good-bye to our friends in Athens, we fly to Thira to start the second leg of our trip.

Chairs in Santorini

Despite it being the first day of the last week of October, it’s sunny and 70 degrees Fahrenheit (21 Celsius). Off come our coats, out comes the sunscreen, and in come the island vibes.

Oia, Santorini

Villages and Towns in Santorini

We take a taxi to stylish Oia, a clifftop village on the northwestern tip of Santorini.

Oia, Santorini

This whitewashed cluster will be our home for the duration of our stay, and as soon as we arrive I feel like I’ve found myself in a quintessential Greek island scene.

Stairs in Santorini

We spend the majority of our 4 days in Santorini in Oia, meandering through the narrow lanes and taking in views of white walls cascading down towards the sea. I’m surprised there are so many visitors here this late in the season, but the bustle lends a buzz to the village.

Oia, Santorini

We shop on the pedestrianized main street in town, taking in all the colors as we do. I fall in love with Atlantis Books, a whimsical bookshop with cave-like rooms, great staff picks, and a painted timeline on the wall. My boyfriend finds some of the local art and textiles to his liking, and we both have to make extra room in our suitcases.

Atlantis Books in Santorini

On other days we explore Imerovigli and Fira. Imerovigli has views of the sea from its stark white walls. The part of town where the restaurants and shops are isn’t as pretty as Oia, but the cliff has several blue domed churches and alluring stairways I fall in love with.

Imerovigli, Santorini

Nearby Fira is the bustling capital of Santorini. It has an abundance of shops, a cable car (I remember riding it when I was 14), and all the blue shutters one could ask for on a Greek island. It’s fun to explore, but we find the shops have more tourist tat than we’d like. By the time we’re done walking around we decide we’ve made a good choice basing ourselves in Oia.

Fira, Santorini

Hiking in Santorini

When we’re not exploring the populated areas of Santorini, we’re hiking. There’s a great hike from Oia to Fira that runs along the cliffs of the island and offers spectacular views into the water-filled caldera below.

Chapel in Santorini

From hilltop chapels with sapphire domes to paths that open up on sweeping vistas, the 3-hour hike pleases our eyes as much as it burns our calories. In fact, we enjoy it so much we decide to hike back, too.

Chapel in Santorini

Restaurants in Santorini

By the time we return to Oia, we’re exhausted and in need of food and drink. Which is good, because the village has no shortage of restaurants. We head to Lefkes for a delicious dinner in a traditional cave, filling our stomachs with as much fresh fish as we can.

Restaurant in Santorini

But even when we haven’t hiked for 6 hours we still have an appetite. We eat two good meals at Candouni, a restaurant with a beautiful terrace adorned with bougainvillea. Other winners include Roka and Fino, and we love the fresh orange juice at Meteor Cafe.

Candouni Restaurant Santorini

Sunset Views in Santorini

And speaking of orange, the sunsets in Santorini are legendary. Every night we find a vantage point from which to watch the sun go down, whether it’s a rooftop bar or a hotel terrace.

Santorini Sunset

And when we see it we’re mesmerized. Even after 4 nights it never gets old.

Santorini Sunset

Neither does Santorini. But there are two more islands on our itinerary, and on our final morning we have to move on. Heading to the ferry port, we take one last look at Oia and start counting down the days until we can return. But we’re off to under-the-radar Tinos next, and there’s more excitement ahead. Stay tuned…

How about you? What would you do with 4 days in Santorini?

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4 Days in Santorini

10 Comments on Lady’s Lovely Guide to 4 Days in Santorini

  1. The pictures are stunning, Santorini is definitely on next autumn’s travel list. We went to Crete last year around the same time and the weather was just perfect and it’s so lovely to escape the cold for a bit.

  2. It looks amazing!! I am travelling to the UK in mid Oct for 2 weeks and thinking if I should take a short trip to Santorini. May I know who did you fly with as the flight tickets are quite exp!

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