Serendipity in Santorini: A Day to Remember

Serendipity: the occurrence and development of events by chance in a happy or beneficial way.

What were the chances… “You’re going to Santorini when?” My husband and I had booked our Windstar cruise of the Greek Isles and two weeks before we were to leave, I found out that a couple from my hometown — very good friends that I’d known most of my life — were going to be staying on Santorini the same week we would be visiting from our ship.

To be rendezvousing on a tiny Greek island thousands of miles away from our Indiana homes in different parts of the state seemed incredulous, a totally unplanned and serendipitous event, and one we needed to make the most of.

I’d planned to book a shore excursion from the ship of this most recognizable of all the Greek islands but since our friends couldn’t join us on a Windstar-sponsored tour, I began searching for a private tour that we could go on together. TripAdvisor pointed me to Private Santorini Tours and I was immediately intrigued by the Grand Circle Tour described on the company’s website, although we ended up with a customized tour that also incorporated a one-hour photo shoot.

My husband, Stephen, and I left our cruise ship, Windstar’s Star Pride, after breakfast on the first tender boat and took a three-minute tram ride from the shore to the top, arriving in the main town of Fira.

A three minute tram ride brings visitors from the shore to the town of Fira.

A three minute tram ride brings visitors from the shore to the town of Fira. (Photo; Debbra Dunning Brouillette)

Our driver, Angelo. (Photo; Debbra Dunning Brouillette)

Our driver, Angelo, with Private Santorini Tours. (Photo; Debbra Dunning Brouillette)



After meeting Angelo, our driver, we met up with our friends, Linda and Marc, who were staying on the island at Suites of the Gods, and then were on our way.

We stopped several times for photo opportunities before arriving in the picturesque and most often photographed town of Oia to meet the photographer, Kristo, owner of StudioKristo.

First photo opportunity with Marc and Linda

A bridal oouple taking photos with a selfie stick was an unusual sight. Santorini is a popular wedding destination. (Photo: Debbra Dunning Brouillette)

A bridal oouple taking photos with a selfie stick was an unusual sight. Santorini is a popular wedding destination. (Photo: Debbra Dunning Brouillette)


A bride taking a selfie? Interesting! (Photo: Debbra Dunning Brouillette)


Photo opportunities abound on the island of Santorini. (Photo: Debbra Dunning Brouillette)


Another photo op on the way to Oia village. (Photo: Debbra Dunning Brouillette)


How would you like to climb these stairs? (Photo: Debbra Dunning Brouillette)

The blue-domed churches and white-washed buildings built into the cliffs provided the perfect backdrops for our photos in Oia (pronounced “EE-ah”).
SLIDESHOW OF OUR PHOTO SHOOT – Take a moment to watch!

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Us with Kristo, as we wrapped up our photo shoot in Oia.

Us with Kristo, as we wrapped up our photo shoot in Oia.


(Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)

The iconic blue-domed church dominates the foreground in the oft photographed village of Oia.

(Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)


Donkey Milk – It’s a Miracle for the Face! (Photo: Debbra Dunning Brouillette)


You can ride a donkey up the cliff, and many do. We chose the tram, and I’m glad we did! (Photo: Debbra Dunning Brouillette)


Fresh sweet corn isn’t something you’d expect to see on Santorini. This stand was in Oia. (Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)

Next, we traveled through the countryside to reach Santorini’s highest point, over 1800 feet, the site of the Profitis Ilias Monastery, dedicated to the prophet Elijah, which dates back to 1711.


Profitis Ilias Monastery (Photo: Debbra Dunning Brouillette)


Profitis Ilias Monastery is at the highest point on Santorini. (Photo: Debbra Dunning Brouillette)


Inside the Greek Orthodox Church at the Profitis Ilias Monastery. (Photo: Debbra Dunning Brouillette)

Icons inside the church at the Profit Ilias Monastery.

Icons inside the Greek Orthodox Church at the Profitis Ilias Monastery. (Photo: Debbra Dunning Brouillette)


Greek Orthodox Bible, Profitis Ilias Monastery. (Photo: Debbra Dunning Brouillette)


View from outside the Profit Ilias Monastery, highest point on the island. (Photo: Debbra Dunning Brouillette)

Our lunch stop was at Forty One Restaurant and Bar, formerly the site of a tomato factory, overlooking the black sand beach.


At Forty One Restaurant. Fantastic food! (Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)


The best Greek salad! (Photo: Debbra Dunning Brouillette)


The black sand beach. (Photo: Debbra Dunning Brouillette)

After our driver delivered us back to the town of Fira, where we began our tour of the island a little over five hours earlier, we spent time strolling through the streets, stopping here and there along the way to do some shopping before finding the perfect small taverna to enjoy an early dinner and toast to the special day we had been able to experience together.

Handmade ceramic dish purchased at Kalipso. (Photo: Debbra Dunning Brouillette)

Handmade ceramic dish I purchased at Kalipso. ((Photo: Debbra Dunning Brouillette)


Kalipso was my favorite shop. (Photo: Debbra Dunning Brouillette)


I wish I’d had more time for shopping! (Photo: Debbra Dunning Brouillette)


There were so many restaurant/bars overlooking the caldera, it was hard to choose! (Photo: Debbra Dunning Brouillette)


(Photo: Debbra Dunning Brouillette)

Ouzeri Greek Restaurant, Fira

We ended up choosing Ouzeri Greek Restaurant in Fira to have an early dinner before going back to the ship. (Photo: Debbra Dunning Brouillette)



Ouzeri’s menu (Photo: Debbra Dunning Brouillette)


Greek appetizers at Ouzeri, Fira, Santorini (Photo: Debbra Dunning Brouillette)


Opa! Here’s to serendipity in Santorini! It was definitely a day to remember.

Although we wished we could stay to watch the sun set over the caldera, we reluctantly said our goodbyes and took the tram back down to the shore where Windstar’s tender boat was waiting to return us to our ship in time to set sail for our next port of call.


(Photo: Debbra Dunning Brouillette)

For more information on our cruise, go to the Windstar Greek Isles Destination Page.
Also on the blog: Ah, Athens! Must-see sites: Acropolis and Acropolis Museum

Ah, Athens! Must-see sites: Acropolis and Acropolis Museum



















19 Comments on “Serendipity in Santorini: A Day to Remember

    • Thanks, Irene! Yes, I am so glad we were able to visit Santorini on our cruise, and that it worked out to share it with our friends from home!

  1. Great post, Debbie. It reminded me so much of the great week that Reg and I spent on Santorini to celebrate our 1st wedding anniversary in 1996. How time flies! I’m so glad you got to explore this incredible island with your friends.

    • Doreen, I didn’t know you had spent a week in Santorini! What a wonderful place to visit for your anniversary. I would love to go back and spend more time there, as my friends did, but glad, too, that we were able to visit several of the Greek isles.

  2. Santorini wasn’t as sophisticated when I visited over 30 years ago, but it was getting busy. I just loved visiting again and seeing it through your tour, thanks so much for letting me see the entire island again.

    • I’m sure it would be interesting for you to go back and see all that has changed…and how much has stayed the same. I’m glad you enjoyed my post!

    • I also love the colors, Donna! All the shades of blue from sea and sky to the blue-domed churches, were my perfect color palette.

  3. Serendipity indeed! I am sure that made your cruise that much more enjoyable. And what a set of wonderful colorful photos, full of sun and life. Thanks for a wonderful posting!

    • Yes, it was an unforgettable day. I am so glad we have the photos from our “photo shoot” to remember the day, as well as those I took on our island tour. I had always wanted to photograph the blue domes.

  4. I love these kind of ‘small world’ stories, and what better place to meet than in Santorini. You just can’t take a bad photo there, either – as your post demonstrates!

    • You are right about that, Jane! There is a new “photo op” at every turn! Santorini is a photographer’s dream.

  5. Absolutely stunning you all look like you are having a wonderful time…I especially like Debbie’s outfit that matches the architecture perfectly. After seeing your photos I now have to add Santorini to my plans when in Greece next year.rend

    • Thank you, Michele! I hope you do make it to Santorini next year. It is a special place. And thanks re: my outfit. I often dress in shades of blue and it was most appropriate for our surroundings.

    • Marilyn, I’m so glad you enjoyed the photos! It was nice to have the photo shoot, too, to help document our day together.

  6. I’ve never seen blue look so brilliant and white look so fresh and clean. Unbelievably stunning, along with the model in the matching blue! I learned a lot from reading this and it’s no wonder it’s a favorite place!

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