Cruising the Greek Islands: Oia, the jewel of Santorini

Santorini was our last stop on our Greek Islands cruise. The first thing I learned? Santorini is too enchanting for a brief port call on a cruise.

cruise greek islands santorini

I was nowhere near ready to leave Santorini after our brief afternoon visit, 1.5 hours of which was spent on the return bus trip between the port and Oia.

Oia, Santorini

On the way to Oia, we crossed rocky, desolate terrain and past the unusual Greek island vineyards, where the vines hug the ground to protect themselves from the wind. We passed through Fira, the unassuming capital of the island, but didn’t stop.


For most of the 45-minute drive, you wouldn’t think you were on a Greek Island at all. Growing up in Australia, islands mean big sandy beaches. I was surprised to learn that the Greek Islands have volcanic origins, which makes them dark, rocky and a little inhospitable.

Oia is another story. The iconic Cycladic village blankets the top of a cliff, cascades down the volcanic hillsides and tempts fate, dangling over the Aegean Sea.

Oia, SantoriniOia, Santorini

Oia is much more colourful than the uniformly blue and white Mykonos. The sea of whitewashed houses and churches was broken up with many colourful buildings, which I wasn’t expecting!

Oia, Santorini Oia, Santorini Oia, Santorini

We started walking as a group, but I quickly got lost in the maze of cobblestone streets. I didn’t mind, because losing the herd meant I could explore at my own pace and could take much nicer photos, sans-tourists.

Oia, SantoriniOia, Santorini architectureOia, Santorini

I found a narrow walkway to a lookout on the edge of the cliff. Halfway along, I peeked over the side and saw a large dog, calmly sitting on a small rocky outcrop below. She sat, seemingly watching a boat sail by. I shared this picture on Instagram and a local commented and told me her name is Emilia!

Oia, Santorini

I eventually ran into my friends and we went to find dinner. We wanted to eat at this beautiful little restaurant (below), but they weren’t doing dinner yet. We were short on time, so we tried somewhere else.

Oia, Santorini

I’m so glad we did! We ate at Pelekanos, a rooftop bar and restaurant, with panoramic views over Oia and the ocean. We saw the beginnings of a legendary Santorini sunset but had to leave probably twenty minutes before it really got going.

Oia, Santorini pelican restaurantOia, Santorini pelikanos restaurant

Most of our group, myself included, was fairly annoyed about this – many had come to see the famous technicolour sunset. Overall, our time in Santorini felt very rushed.

We left it so late that we practically had to run back to the tour bus, but I found time to duck into a jewellery shop and pick up a pretty blue bracelet. We got a scolding from the teacher-like tour guide when we got to the bus, but more than half of our group was even later than us! It was pretty clear that no one felt they had enough time on the island.

I loved my cruise of the Greek Islands, but if you really want some time to explore, I’d advise against a cruise.

Oia, Santorini Oia, Santorini

Since the Greek Islands cruise, I’ve been on a seven-day cruise around New Caledonia and Vanuatu. These destinations were ideal for a cruising holiday because we had most of the day in each destination. I didn’t feel rushed because at each destination there were fewer things I wanted to see, mostly I wanted to snorkel and sit on the beach.

Before the trip, I was hesitant about stay on the islands because they are quite expensive and potentially super touristy.

We went in September, a few weeks before the islands shut down for the winter, so the crowds were thin. My afternoon on the island was enough for me to be totally spellbound by its beauty and has confirmed that yes, Santorini is worth spending the big bucks on staying for a few days. I’d love to come back early one September and stay for four or five days, visit a winery and the caldera outside Fira and of course, enjoy many Santorini sunsets.

Have you been to the Greek Islands? Have you been on a cruise, and if so, where to? 

12 thoughts on “Cruising the Greek Islands: Oia, the jewel of Santorini

  1. I came across this post at a perfect time! I’m going to Santorini the beginning of October and cannot wait. Also I loooove rooftop bars so I’m definitely checking out Pelikanos!!

  2. Beautiful place! It’s been a while since I’ve visited Santorini, but I have never forgotten the loveliness of the city! I hope you had gone wine-tasting; that was a memorable experience for me!

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