No Regrets!

The flight over to Santorini offered views of several cute little rocky islands. Santorini is much bigger than the others. Coming in from the east offered a close-up view of the massive peak of Profitis Ilias. Had no idea there were mountains this big out here.

Just outside of the airport was a shuttle bus waiting to take me to Fira (FEE-dah), where my hotel is. They dropped me at the bus station, and after a short walk, I was at Thalia’s Apartments. Thalia herself appeared to greet me and give me the lowdown on her place and the island. She’s very sweet and couldn’t believe I was in my late 30’s. I’m loving it.

In late afternoon, I made my way to the famous Santorini view across the water. Crossing the main street is an adventure, with cars and buses and scooters zipping both ways unpredictably. My walk continued past the souvenir shops and and up the hill and to the edge of the cliff overlooking the water. And then it opens up. The view is immense and breathtaking. No photos can prepare you for that. Cruise ships on the water below are the only thing that give a sense of scale, and they look like toys.

Geologically, this place is fascinating. Santorini was once a much larger island until a huge volcanic explosion in 1600 BC blew out the middle of it. What’s left is a larger ring island with most of the tourist amenities and a few smaller, mostly uninhabited islands. In the middle is the massive crater which is now filled with ocean.

Walking up and down the alleys of Fira, there are bars and restaurants with terraces built out over the cliff, each of them reaching for the best possible sunset view. Souvenir shops sell t-shirts and bracelets and magnets.

As the sun began to set, I parked myself at the Iriana Café, a little terrace playing amazing loungy covers of my favorite songs. Sipping a mojito, I watched as the reddish sky slowly faded to black and the Big Dipper revealed itself. The beauty and the music and the mojito were perfect. This was one of those happy moments that sticks.

When I was first planning this trip, I half-jokingly sent invitations to a few friends to meet up with me somewhere along the way, assuming that none of them would take me up on it. I was shocked when Ruth, an Israeli girl I met on a dating site about 6 years ago but never actually met, told me that she was spontaneously buying a last-minute ticket to fly out to Santorini and meet me. Wow. Completely nuts, completely awesome.

I met Ruth at the bus station, and we hit it off immediately, just like I thought we would. I took her to my favorite spot at the Iriana Café so that she could enjoy her first Santorini sunset. We got a drink, and I introduced her to my selfie stick.

Later that evening, Conrad arrived. Very cool and weird to see a familiar face after being away for so long. I introduced him to Ruth, and the three of us would spend the next few days exploring Santorini.

Conrad and I rented scooters, perfect for zooming up and down the island, exploring black and red sand beaches, and finding amazing views over the caldera. We treated ourselves to delicious meals at places recommended by friends and by TripAdvisor. One day was spent exploring the black and red sand beaches on the east and southern coasts of Santorini.

From FIra to Imerovigli to Senor Zorba’s to Oia, we enjoyed a beautiful sunset from a different spot each night.

And each night, we’d dance at Highlander Bar and Murphy’s until the wee hours of the morning. Good times.

Despite hordes of people, it seems to me that tourism here is still in its adolescence. Much of the island is undeveloped, and there are no giant chain hotels on the island. I wonder if there are Greek regulations prohibiting them.

On our last evening in Santorini, we took our scooters up to Oia (EE-ah), the town on the northern tip of the island famous for its sunset views. Driving our scooters along the cliffs to Oia, the views are spectacular.

Through regulation or unprecedented cooperation, all the rooftops in Oia are white. And all the domes are painted a uniform shade of blue. What’s the name of that blue? Is there a Pantone number for it? The uniformity of the architecture and colors really helps the photos, but the lack of clouds doesn’t. We didn’t see a single cloud in Santorini, which makes the sunsets a little less interesting to look at.

The last day in Santorini was rough for Conrad. He lost his iPhone on one of his scootering runs and he dropped and cracked his GoPro. 🙁

Five days was just about right to see and do everything on the island. This morning, Conrad and I said goodbye to Ruth and headed to the marina to begin the next chapter of our adventure, a 10-day G Adventures sailing trip through the Greek Islands!