
Santorini. Those surreal blue and white pics you see on calendars, guide books, travel agents and pretty much everywhere you see the word Greece. It’s a major cruise ship destination and apparently the crème de la crème of the Islands. It’s also a fair distance from major boat charter bases, so you need a decent weather window to get there. Lucky for us, we got that! Was it a piece of cake getting over there, not really.
We set off at midnight with Heath and Dalen getting us off the cramped dock and into the open water. The waves weren’t large, only 3-4’ significant, but they were from dead ahead. There wasn’t enough wind to sail without any help from the engine, but we were able to throw up the sails to help steady the ride a little. That always helps alot with the bouncing about. Zach and Andrew had the 2:00-4:00 shift, while Bonnie and I did 4:00-6:00. It’s obviously not much of a shipping channel, as we saw very few other vessels. The stars were brilliant and it was gorgeous out. When I took the helm at 4:00, you could already clearly see the lights of Santorini in the distance even though it was at least 22 nautical miles away.

We approached the island from the East, rounded the northern tip and moored by the inner plug. This is what they call it, as the whole area is a large volcano. It was, in a word, spectacular. The island has sheer cliffs along the inside with white city nestled along the tops. By all appearances they built as absolutely close the edge as possible and it looks like if one rock would shift, all the houses would slither and slide into the sea. White step paths occasionally zigzagged up the cliff, and near the main town, Fira, there was a tram to bring people and supplies up. Four enormous cruise ships were languishing in the bay and tenders were constantly steaming back and forth, ferrying people to shore and back. Excursion boats hauled people to the inner “plug” where you can hike around volcanic craters and see a few puffing fumaroles.
When I googled what to do at Santorini, most of the top ten things involved a catamaran, so that was nice since we had brought ours along.
Tour the inner bay on a catamaran ✅
Dinner on a catamaran ✅
Sunset from a catamaran ✅
Private tour with your friends on a catamaran ✅
You get the picture. So, we started by hiking the trails of the plug and gazing in awe at the blue, blue sea, the shockingly rugged cliffs and the beautiful town perched on top. After that we headed to the main island, where we tied off on an ancient, rusty pier in the middle and took our dinghy to the little harbor. You can’t actually dock your private vessel there. It’s only for the commercial ones and they certainly keep it hopping! By the way, we can easily fit nine adults in our dinghy. Our bums might dip into the water a little and we may be mistaken for a boat of refugees, but that’s nothing.
Just so you know how steep and high this really is, we took the tram up. Yes. We did. It just looked a bit daunting to climb that much. Also there was the business of not having all the time in the world.

We got to the top and into a crush of people, beggars and tourist shops. It took less than 10 minutes for us to find a rental company that could supply us with a couple little cars and we headed off to explore the real island.
The eastern part of the island has more of a gradual slope down to the water and its full of terraced farm land. They grow things like beans, cucumbers and grapes. It looked a little dumpy some places, but also very pretty. The town of Oia is located on the NW end of the island, and it’s exactly how it looks in pictures. I was rather surprised to note that most pics are really truly not photoshopped. It is absolutely gorgeous! We walked the twisty streets, climbed up and down uncountable staircases and stopped for an afternoon crepe break in a tiny cafe called Vitrin overlooking it all. Imagine, hot sun shining on white buildings, brilliant blue sea sparkling below, hot pink bougainvillea and a crepe smothered in Nutella with a large scoop of vanilla ice cream on top. Can life get much richer?

The SW tip of the island had a black sand beach that we strolled on, although I was much more attracted to the areas of washed up pumice rock. Large washed up areas of little rocks that you could sit in and swirl your hands in and it almost felt like you were swirling packing peanuts around. You could also have rock fights with zero negative repercussions. By the way, it is impossible not to duck when a rock comes flying at you, even if you know it won’t hurt.
Our cars had to be back by 6:00 and Heath and I needed to return to the boat as dark was approaching and we hadn’t turned our anchor light on. The line for the tram was so backed up we took the zigzag path, running all the way. It was technically closed for some construction, but clearly others were going around the barriers so we hardly slowed when we came to it. Bonnie was with us as well since she was on supper duty. We hopped into the dinghy and sped off, cheerfully waved and goodbye’d by a couple of strangers. The rest of the crew explored a little more but mostly shopped for provisions as we will be a little out of civilization for a couple days after this.
We spent the evening eating and gazing at the views. All the cruise ships were gone by 9pm and we were ready for bed. It seemed a little presumptuous just to go to sleep next to such a very solid, immovable pier, but the wind was supposed to hold us off it in the night and we chose to trust.
It held us off all right, in fact, the wind really kicked up in the night and we bounced and shook on the end of our leash in a rather annoying fashion. Rather that than bumping into it I guess.
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