The tour was a gift from our travel agent. A day in Santorini with a well-known guide, someone who was passionate about Greece and – as a bonus – was a photographer. “He has shown some very famous people around the island,” our agent had said, “and he will take wonderful pictures of your family. You will love him!”

We typically book every aspect of a trip ourselves, but with cruises, we always work with a travel agent. This was the first time anyone had arranged a tour for us. It was a generous gift, and it was especially welcome in Santorini, where we would need transportation to get around. We thanked our agent profusely and didn’t give the tour another thought.

A month later, we arrived in Santorini. It was a glorious summer morning, and the island loomed high above the sea. Our ship anchored offshore, requiring a tender to take us to the base of the island, where we were faced with a transportation choice for the trip to the town of Fira at the top: cable car or donkey. We agreed on the faster cable car, especially with a guide waiting for us.

The guide wasn’t there, but we were a few minutes early, so we waited at the cable car platform. Various guides holding signs with their group’s names waited  with us, meeting and greeting and moving on to their waiting cars and vans. Group after group arrived and left, and still we waited. I’m not sure why it took so long for us to realize that our tour wasn’t going to happen, but finally after half an hour, we began to lose hope.

We didn’t have a cell phone with us – this was 2006 – and agreed that Herb would walk into town to find a phone while the kids and I would wait at the platform in case our long-lost guide finally appeared. When Herb phoned the tour office, he was told that the gentleman who ran the office and was supposed to show us Santorini was unable to do the tour. He had asked someone to take his place, but apparently she had forgotten and they would send her as soon as they could.

We had been waiting over an hour when she finally arrived. An unsmiling, 30-something-year-old woman who had not planned on showing anyone around that day and clearly was not happy about being there. Her accent was unmistakably not Greek. She was from Queens, New York, an expat who had moved to Greece because of her family’s heritage, but who never quite took to the place and was moving back as soon as she could.

We told her we wanted to see Oia (pronounced EE-Ah), the village featured in those iconic photos of Greece – white buildings with blue-domed roofs perched on the side of a cliff and looking out on the bluest of seas. She sighed as she drove us there. “It’s way too touristy,” she told us. And after giving us a brief overview of the town, she said she would meet up with us when we were done.

The words “done” and “Oia” should never be used in the same sentence. I found it impossible to be done with anything there – the enchanting views, the pastel-colored houses, the friendly shopkeepers and food vendors. We tasted Santorini-grown pistachios, honey-covered peanuts, olive oils and caper leaves, which can only be found on the island. I wanted to bottle up a little bit of everything and pack it in my suitcase. If Oia was for tourists, then I was very happy to be one!

Our family in Santorini, Greece. 2006.
Emily & Herb
Emily and Herb and the charming architecture of Oia.
Oia Houses
Blue-domed roofs in the distance.
Oia Other View
Looking out on the Aegean Sea.

Our guide drove us to a café on the beach for lunch and ended the tour at the Fira cable car platform. We wandered around the town and headed back down the hill on the cable car. The donkeys would have to wait for another visit. We hadn’t seen everything that we’d planned, but we had salvaged the day and had made it to beautiful Oia.

And we had learned a few Travel Lessons:

Travel Lesson #1.

Confirm and reconfirm. ALWAYS. Airplanes, trains, hotels, tours, people. It doesn’t matter how recently you made the plans or how confident you are that everything is set. This tour was tricky because it was a gift. I assumed the travel agent had taken care of everything and felt it was inappropriate to contact the tour guide directly. In retrospect, I should have emailed the guide, introduced myself and our family, given a brief overview of what we wanted to see and confirmed the tour. And I should have copied the travel agent on the email.

Travel Lesson #2.

Bring your cell phone, even if you don’t think you’ll need it. Today we always do. You never know. And Google Maps can be a lifesaver.

Travel Lesson #3.

Make sure you have contact information for everything you’ve booked – names, phone numbers and confirmation numbers. Bring copies of receipts or make sure you have confirmation emails on your phone.

Travel Lesson #4.

Always have a back-up plan. Had I done my homework before the trip, I would have discovered there was bus service between Fira and Oia. And I should have checked out other tour options or car services, “just in case.”

Travel Lesson #5.

Make the best of the moment. Even with the most meticulous planning, glitches happen. Surprises and disappointments are part of traveling. The trick is not to let them ruin the moment. It would have been easy for our guide’s negative energy to seep into our spirits in Santorini that day. But the beauty of what we saw and experienced there made that impossible.

We may have been stranded for awhile…but oh, what a place to be stranded.

Looking Out to Sea


  • Thank you for sharing your photos and thoughts about traveling and I’ve taken your tips to heart. You have a lovely attitude after such an obvious disappointment with the tour guide.

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