Santorini; Or: The Great Octopus Hunt

Around a decade ago I found myself in Astoria, Queens sitting across a dinner table from my pal Carey, who was trying to convince me to try the grilled octopus he had just ordered. “Trust me,” he said. “I was skeptical, too.” Or something like that. I’m using some dramatic license here. I was definitely skeptical, though. Octopus? Like, the grabby bastards that pulled wooden ships to their wat’ry doom? No, that was kraken, he explained. I, a Missouri rube, was not as enlightened as Carey, a recent Missouri to New York transplant. The octopus arrived. A pink and white tube of meat, charred and half-covered in blackened suckers, lay on the plate amid a swirl of olive oil dashed with oregano. It didn’t look appetizing, but my culinary philosophy was “I’ll try anything once.” Carey cut himself a chunk, popped it in his mouth, and moaned slightly.

My first bite was more tentative. A little piece, with no suckers. It practically melted on my tongue. The flavor came through as something like chicken, with hints of char from the grill and a bit of seasoning from the olive oil and oregano. The texture, though, was what really elevated it. Firm, yet buttery with enough tooth that you knew it was meat, but so tender that it couldn’t possibly be meat. “Try a bite with the suckers,” Carey said. “They’re the best part.” I did. They crunched a little, adding even more texture to an already mind-blowing mouthfeel. He was right. They were, in fact, the best part.

Reader, I’ve been chasing that high ever since. The chase has stretched from New York to Florida, from London to Lisbon, from Italy to–most recently–Greece. I’m not saying I planned a family vacation around my hunt for the world’s best octopus, but I’m not saying it wasn’t on my mind, either.

Planning for this started in May. I had a milestone birthday in October, and it was the same week the kids were out of school for their midterm break. With Covid interrupting travel for the last two years, I wanted to do something special. My first thought was Portugal, but I’ve been there a number of times for work, and I wanted to go somewhere I hadn’t already been.

A few years ago I was sitting in a bar in Reno talking to one of the sales guys at work, and he mentioned how the most amazing place he had ever been was Santorini. This was a guy who basically lived on the road and had been successful enough in his career to be able to go anywhere he wanted. That comment lodged itself in my brain. In May, when I was looking at destinations, Santorini came to mind. With the busy season in Santorini being in the summer, there were plenty of hotel rooms and flights in late October. I checked with Carissa–who was convinced the moment she saw the photos–and booked the trip.

After some quick research, there were three things I wanted to do, for sure. Take a boat tour of the island’s beaches, hike down the island’s spine from Fira to Oia (ee-UH), and continue The Great Octopus Hunt.

If you look at a map of Santorini, you’ll see that it’s a crescent-shaped island with more islands in the middle and another off on the west side.

Originally Santorini was one large, circular volcanic island and home to a village on the southern edge near where the map shows Akrotiri. That lasted until about 1700 BC when the volcano erupted. Much of the island ended up submerged and what was left ended up covered in lava, ash, and mud. The village was inundated with mud, and the island’s physical shape was forever changed.

Our first full day included breakfast at the hotel on the patio outside our suite. When I booked the rooms, I didn’t realize how nice the breakfast would be. That was a delightful surprise. We wandered Fira, the island’s capital and largest village, for a bit, then caught our bus to Vlychada on the island’s southern shore. The boat tour took us west past Red Beach, White Beach, the black cliffs, and the island’s caldera. Red Beach is a product of the iron the volcano ejected. White Beach–only reachable by boat–is named after the white cliffs overlooking it and is actually a black pebbly beach with shockingly clear waters.

The black cliffs (I’m struggling to find the actual name) are another product of the volcano and include a bunch of linked caves only reachable by divers. I was hoping we would have time to hike on the caldera, but the tour only included a swim in the volcano-warmed waters near it. The scenery wasn’t as impressive as the beaches, but it was interesting to swim in such sulfur-rich water. Well, I thought so until I realized that my damp swimming shorts were stinking up the closet two days later and I had to give them a thorough rinsing.

The real pinnacle of the sailing was the sunset. We had already seen one sunset from the crater’s rim at the hotel, but seeing it from the water was even better.

The second full day was the hiking day. I led the girls out of Fira, through the neighboring villages of Firostefani and Imerovigli, and out to Skaros Rock. The stairs down to the rock ended at the ruins of a fortress that fell into disuse after a series of earthquakes in the 1800s. We wanted to climb out to the top of the rock, but the path up to it involved more actual climbing than we were prepared to do. (Two of our party thought hiking in their Air Force Ones was a good idea.) After Skaros we climbed back up to Imerovigli and continued along the trail toward Oia. A few different churches clung to the hills, their white walls and blue domes little oases amid the dusty rocks and withered grape vines. It wasn’t hot, but it was definitely warm, and the anti-hiking whining crescendoed a kilometer short of Oia.

Fortunately, we made it to Oia without anyone dying of dehydration or sunstroke, and a bit of ice cream helped revive morale. We wandered through the warren of alleys that is Oia–I may have led the party astray with a poorly chosen turn–and made our way down another long flight of steps to Ammoudi Bay and a little taverna right on the waterfront. 

The Great Octopus Hunt resumed at Dimitris Taverna with a local beer, a half liter of local white wine, and an order of grilled octopus. My expectations were tempered. Not only do I still have a high bar to clear from Taverna Kyclades in Astoria, but I’ve also had A LOT of mediocre octopus over the years. Did you know that people willingly make boiled octopus? And that they serve it cold? I learned that the hard way. A few times. Dimitris, though. Dimitris delivered.

I’m not going to say it was better than Taverna Kyclades, but I will say that they are both S-Tier. We ended up ordering a giant seafood platter that included more octopus, but the second order was a bit tough and overcooked. It was still better than the boiled appetizers I’ve had at other places, but only B-Tier at best. 

We had three full days in Santorini, and I didn’t have concrete plans for day 3. The options were to catch the bus to Akrotiri and see the ruins, book a boat to take us to the caldera for a hike on the active part of the volcano, or tour a winery. All three were supposed to be reasonably fun activities, but Carissa and I are both history buffs (and the girls refused to go hiking again). We went down to Akrotiri and wandered the ruins. In retrospect, I probably should have booked a guide, but it was plenty impressive to see the village and read the plaques describing the excavations. The building itself was fascinating, too. It had wonderful natural light and was pleasantly cool inside. All with minimal energy usage. 

We watched the sunset at the hotel again, then wandered Fira to find dinner. I had a few places in mind, but they were a bit too low-scale for our tastes that evening, and my nicer option was already closed for the season. After a bit of recalibration, we found a place on the edge of the cliff and settled in for another round of The Great Octopus Hunt. As ever, I assumed the worst. We ordered another big seafood platter, and the octopus was actually pretty decent. Not quite to the heights of the first taste in Greece, but better than the second batch. We’ll call it A-Tier. (If you’re wondering how S-Tier is better than A-Tier, just roll with it. You clearly don’t spend enough time on the internet; that’s probably for the best.)

It wouldn’t be a family vacation if everything went to plan. We had a minor wobble Sunday evening. The plan was to take the train to Gatwick, stay at a hotel by the airport, and fly out early Monday morning. We made it as far as Clapham Junction where we learned that there were no trains leaving Victoria, therefore our path to Gatwick was blocked. We solved that problem by paying for an Uber to take us to the hotel. The real wobble came in Greece on the way home. We were flying Ryanair to Milan and EasyJet from Milan to London. I was able to check in online for the EasyJet flight with no issues. When I tried to check in for Ryanair, it gave me an error on the youngest child’s birthday. After trying two browsers and the airline’s app, I figured I’d just go to the airport a little early and get a boarding pass printed. LITTLE DID I KNOW that Ryanair charges 55 EUROS PER PERSON for in-person check-in. I tried to explain that I would have done it online but their system was giving me errors with no clues on how to solve them, but the clerk manifestly did not care. The message was to pay up or find another airline. I grudgingly paid because what else was I going to do? There was some follow-on drama with the staff that I don’t want to get into here, but we were ultimately able to get out of Greece on schedule and get home on schedule, if unnecessarily poorer. It was absolutely extortion, and it will be a good, long while before I give Ryanair another cent. 

Setting aside Ryanair being shambolic, we had a lovely trip. The boat tour was phenomenal. The company was wonderful. The Great Octopus Hunt was a resounding success. The hunt, however, will continue. Much like life itself, The Great Octopus Hunt is about the journey more than it is the destination. May your own journies be as fulfilling and delicious.