Santorini Honeymoon REGRET: The Trip That Made Me Want to Go Back

My wife and I visited Santorini for our honeymoon in September. The weather was perfect, and I had imagined the island exactly as it appeared in all the photographs: white buildings covering the cliffs, blue-domed churches, narrow streets, flowers hanging over white walls, and the Aegean Sea stretching endlessly into the distance. 

But when we first arrived, Santorini didn't look anything like the pictures. 

And, as I would soon discover, there was a reason.

Arriving in Santorini

We decided to fly to Santorini rather than take the ferry. I knew the ferry would take considerably longer, and for a honeymoon, I didn't think spending hours getting there was the best use of our time. 

We arrived during the daytime in September, with beautiful weather waiting for us. I remember looking around the airport and thinking, Where is the Santorini I've seen in all those photographs?

There were no endless rows of white houses with blue roofs. No dramatic cliffside views. Nothing that immediately looked like the Santorini I had imagined.

At the time, I didn't realize that the most famous part of Santorini was concentrated in a few particular areas.

That would become an important lesson during our trip.

Choosing the Wrong Hotel for a Honeymoon

For our honeymoon, I booked Astarte Suites in Akrotiri, on the southern part of the island.

The hotel itself was actually very nice. Our suite was spacious, with a king-size bed, a sofa, a patio with a table and chairs, and a jacuzzi inside the room. There was also an infinity pool overlooking the ocean.

But looking back, I made one important mistake. 

I should have spent more time researching where to stay. If I had done more research before the trip, I would have realized that Fira and Oia were the places to be for the classic Santorini experience.

Our hotel was perfectly fine for a casual visit to Santorini. But this wasn't a casual visit.

It was our honeymoon.

The jacuzzi was another small surprise. We expected it to be hot, but the water temperature couldn't be raised as much as we wanted. The hotel could only increase it to a certain point, and it ended up feeling more like getting into a warm swimming pool. They only have jacuzzi to cool off your body temperature rather than heating it up.

Still, the hotel had a beautiful setting, and at the time I thought I had made a good choice.

Later, after seeing the hotels in Fira and Oia, I changed my mind. If I could go back, I would spend whatever I needed to get the best hotel I could afford in Fira.

That's one lesson I would give any husband planning a honeymoon:

Happy wife, happy life. Not that she wasn't happy, but you know what I mean.

An Unexpected Wedding Invitation

One of the strangest and most memorable things about our trip happened before we even really began exploring Santorini. On the airplane, my wife and I were sitting next to another couple. We started talking casually, as people often do on flights.

We asked each other why we were going to Santorini. They told us they were going there to get married. Somehow, during our conversation, they invited us to their wedding. We barely knew them. But when we arrived in Santorini, we actually went and signed their marriage license as witnesses.

Their wedding was held at a hotel in Fira, and that was the moment I realized just how different our hotel location was. Their hotel had almost the same kind of setup as ours, but the difference was the view. In front of them were the famous white buildings with blue roofs, stretching along the cliffside, with the sunset right in front of them.

Standing there, I remember thinking:

This is where we should have stayed.

The wedding itself became one of the most unexpected memories of our honeymoon. We were the only guests and never knew that the wedding could be this simple. We had arrived in Santorini as newlyweds, and somehow ended up attending the wedding of a couple we had met on the airplane.

You couldn't really plan something like that.

Finally Finding the Santorini From the Photographs.

Because we rented a car, we were able to drive around the island. The driving wasn't always easy. For one thing, the rental car had a manual transmission. I wasn't particularly comfortable driving a manual car, so I was basically learning as I went. 

Then there were the roads.

Some of the roads leading toward the beaches were little more than narrow dirt roads, sometimes just wide enough for one car even though traffic could come from both directions. In some places, there were no guardrails at all, with the edge of the road dropping toward the cliff.

At one point, I had to make a U-turn on one of those roads. My wife got out of the car. She says she wasn't scared. According to her, she simply wanted to make sure the car wouldn't go down the cliff. 

I'll let you decide which version of the story you believe.

But driving around the island helped us understand Santorini. We discovered that the famous white buildings and blue roofs we had seen in photographs were concentrated around Fira and Oia.

Then we arrived in Fira. 

Everything changed. Fira Was the Santorini I Had Imagined. Inside the main tourist area of Fira, suddenly everything looked like the photographs. The buildings were incredibly white. Blue doors stood out against the walls. Flowers hung over the edges of buildings and walls, adding color to an otherwise almost entirely white landscape. Restaurants and shops lined the narrow streets.

People were everywhere, but they generally seemed happy. They walked slowly, stopped to take pictures, looked out toward the sea, and enjoyed the atmosphere. This was the Santorini I had expected to see when we got off the airplane. We walked along the cliffside and looked across the caldera. From the restaurants, we could see the white buildings stacked along the edge of the island.

It was simply a beautiful place to sit and watch. We eventually found a restaurant where we could sit and look across the cliffside buildings. We didn't have to do anything special.

We just sat there. Sometimes that's what makes a place memorable.

Oia and the Sunset Crowd

Oia felt different from Fira.

It was more touristy and much more crowded, especially around sunset. This was clearly the place where everyone gathered to watch the sun go down. We walked through the narrow streets and finally got to see the famous blue-domed churches up close. We also found restaurants where you could sit near the ocean and watch the sunset. Windmills stood against the landscape, and Greek flags moved in the breeze.

There were plenty of people around us, all waiting for the same thing. The sun slowly began to disappear. Normally, a large crowd would make it difficult to describe a sunset as peaceful. But somehow, once the sun started going down, everything seemed to slow down. We watched the light change across the white buildings and the sea. Despite all the people around us, it became one of the most peaceful and memorable moments of our honeymoon.

A Winery With a View I Still Remember

We also stopped at a winery during our time on the island. 

The winery had an incredible ocean view, and the setting itself was worth the visit. The wine, however, was another story. There were many different varieties, but I can't say that I particularly enjoyed the taste. Maybe it was because of the grapes and the volcanic soil where they were grown. Whatever the reason, the wine wasn't really to my palate.

But I still remember the winery. Not necessarily because of the wine. I remember sitting there with the ocean in front of us and looking out over the landscape. 

Sometimes a travel experience stays with you for reasons that have very little to do with the thing you're actually there to experience.

Santorini's Beaches Weren't the Highlight

We visited some of Santorini's beaches, and they were nice. The volcanic landscape gave the sand and rocks unusual colors, which made them different from other beaches we'd visited. 

But honestly, I didn't find the beaches particularly special.

They were nice, but they weren't what made Santorini memorable for me. The drive to some of them, however, was memorable for completely different reasons. Getting there meant navigating those narrow roads, and some of the routes felt more adventurous than they probably needed to be.

Looking back, I think Santorini's greatest attraction isn't really its beaches.

It's the landscape, the villages, the cliffs, the buildings, the sunsets, and the way everything seems to come together around the Aegean Sea.

Swimming in Volcanic Water

One experience that was much more unusual was our volcanic-area tour. We booked a boat tour and went out toward the volcanic area. We didn't do a long hike. Instead, we had the chance to jump into the water and experience it ourselves.

We did a little snorkeling, but the most interesting thing was the temperature of the water. In certain areas, the water was surprisingly warm—warm enough that it felt almost like a natural hot spring. My wife wasn't completely convinced that this was a good idea. She was worried that the water might actually burn us. And then there was the possibility that the volcano might suddenly decide to erupt.

We survived both possibilities. The volcano stayed quiet, and neither of us got burned. It became another one of those strange little honeymoon memories that I still remember clearly.

The Food We Still Remember

Food was another important part of our Santorini experience. One of the best fish we had was branzino. It was so good that we actually went back to the same restaurant and ordered it again.

The octopus was also surprisingly tender and delicious.

We ate gyros and drank beer many times because they were easy, casual, and convenient when we were out exploring.

But my wife's favorite meal may have been much closer to home. The seafood pasta at our hotel was so good that she told me it was the best seafood pasta she had ever had.

There was also a restaurant called SEAGULL that offered a beautiful view from the table. Finding it wasn't particularly easy, but once we got there, the view made the effort worthwhile.

Those meals became part of the trip just as much as the sightseeing.

What I Would Do Differently

Looking back now, there are several things I would change. The biggest one would be the hotel. I would stay in Fira. I would spend more money on the hotel and make sure we had the kind of view we saw from the wedding hotel—the white buildings, blue roofs, and sunset right in front of us.

For a normal trip, I think staying in Akrotiri could be perfectly fine. But for a honeymoon, I would choose differently. 

I would also rent a car again. 

The driving wasn't easy, especially with a manual transmission and some of those narrow roads, but having a car made it much easier to explore different parts of the island. We could drive to Fira, Oia, beaches, wineries, restaurants, and other parts of the island on our own schedule.

For us, that freedom was worth it.

Santorini Made Me Want to Go Back

When I think about our Santorini honeymoon now, I don't remember just one beautiful photograph. I remember the unexpected wedding invitation from a couple we met on the airplane. I remember the crowded streets of Oia and everyone waiting for the sunset. I remember my wife getting out of the car while I attempted that cliffside U-turn. I remember jumping into the volcanic water and wondering whether it was actually a good idea. I remember the branzino that was good enough to make us return to the same restaurant. And I remember sitting at a winery with a beautiful ocean view, even though I wasn't particularly impressed with the wine.

Most of all, I remember realizing that Santorini was bigger than the photographs I had seen before the trip. You have to drive around, explore, and discover where the famous views actually are.

But maybe that's part of why I still think about Santorini.

I didn't see everything the way I wanted to.

I didn't choose the perfect hotel.

I didn't love every glass of wine.

And I certainly didn't master driving a manual car on a cliffside road.

But after all these years, when I think about Santorini, my first thought is simple:

I need to go back.

Let's Go!

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