4 Days in Santorini

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.

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

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.

Villages and Towns in Santorini

We take a taxi to stylish Oia, a clifftop village on the northwestern tip of 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. We’re staying at the Canaves Oia Sunday Suites, a gorgeous hotel with stunning views.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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