September 5, 2025

I have dreamed about Santorini since I first had seen a picture of the whitewashed buildings, the blue-domes, and the blue water in the background. I bought a calendar once and I think I kept that picture for years after because I loved that image so much. When Andy and I got engaged – this was where I originally wanted to get married.

One thing led to another and the universe had other plans and we got married in the Dominican Republic instead. This was the port stop that I was most excited to visit because of how long I had dreamed about Santorini for – and honestly, it didn’t let me down.

Santorini is one of Greece’s most iconic islands, but what makes it truly unique, is that it sits on the rim of an active volcanic caldera. The result of a massive eruption thousands of years ago that shaped its dramatic cliffs and crescent shape.

One of things to note about Santorini is that all of the villages are on the cliffs, and tourists have limited options to get to the top. You can climb up 588 stairs to the top of Fira, ride a donkey, ride a cable car and pay 10 euro per person (one way), or book an excursion with the cruise ship who will arrange travel for you.

We opted for the last option, which took the guess work out of it for us. It did mean we had an early wake up call for us, but we got on tender who brought us over to the new port where our bus was waiting for us. These roads were teeny tiny and would have had anyone who was afraid of heights pinching their eyes closed and praying for it to be over as quickly as possible.

Our first stop was Oia, with its winding alleys and the famous blue domes. We were one of the first busses to pull into the parking lot, and our tour guide was so excited that she hustled us to the meeting point and told us to get to the “Instagram” point as quickly as possible because the crowds would be getting there soon and the lines would get long for the picture.

This is where things got funny. Andy and I ended up splitting up on accident because she told us that the there were two different vantage points for the domes, and both of us were in too deep with our respective lines. Andy’s line moved faster. He then came over to my line to be the ever-dutiful Instagram husband and take my pictures. Another bucket list item secured!

Our next stop was a winery – Artemis Karamolegos. We sampled three wines: a crisp white Assyrtiko, a dry rosé Assyrtiko, and a sweet wine that they were famous for, the Vinsanto. Santorini has some of the oldest grapes in Europe because they were resistant to phylloxera, which had devastated the rest of Europe’s vines. We enjoyed our time there before getting back on the bus for our last stop.

We made our way to the capital, Fira. This is where most tourists make the pilgrimage from the old port (the 588 steps or the donkey route). Thankfully, we were already at the top. We had an hour here, so we made our way to the edge and snuck a peek of the caldera and the donkeys before doing a little shopping.

We made our way back to the cruise ship after our stop in Fira. Andy and I discussed, and we realized that everything had worked out the way it was supposed to. We were supposed to get married in the Dominican Republic. Santorini was stunning, and beautiful. But it was small – and I think we would have been bored after a day or two. It’s funny how things work out and you just don’t know it at the time!

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