Santorini just might make for the perfect holiday. Not only is it easy on the eyes, a stay on the Greek island can be as active or as leisurely as you’d like. Go sailing, take a hike, explore ancient ruins, or do nothing but sip wine and gaze at the sea. Even after spending six days there, it was one of the few places I didn’t feel ready to leave when the time came to pack up and move on. The bulk of Santorini’s visitors dock for a day, barely scratching the island’s surface. But linger if you can. You certainly won’t regret it.
Hike along the coast
The five-and-a-half mile walking trail linking the villages of Fira and Oia might well be the best hike I’ve ever done. I like my outdoor efforts to come with a payoff. If I’m going to suffer and sweat hiking for several hours, there had better be something spectacular waiting at the end like a sweeping mountain vista or a sparkling blue lake with icebergs floating in it.
Given that criteria, the Fira-to-Oia trail is the reluctant hiker’s jackpot—there is a payoff with almost every step. The clifftop trail winds along the island’s edge overlooking the caldera. Across varied terrain, up and down hills, we walked on…and on…and on. Occasionally we’d catch a glimpse of Oia like a mirage off in the distance, its cluster of white buildings gleaming in the sunshine.
Wanting to beat the intense heat, we set out around 8:30 a.m. Including numerous stops for photos and breathers, it took us nearly three hours to reach Oia. To our surprise and delight the trail was nearly empty, a refreshing bit of solitude on a crowded island.
Get those iconic shots in Oia
Even if you’re not staying in Oia, visiting the town is a must. Perched high above the sea on the end of the crescent-shaped island, Oia began as a Venetian fortress during the Middle Ages. It was later part of the Ottoman Empire and then became a major shipping port in the late 18th and early 19th centuries. Simply strolling around Oia offers plenty of photo ops of centuries-old castle ruins, windmills, blue-domed churches, and cave houses etched into the cliff. Try to avoid visiting Oia when cruise ship crowds are at their thickest by checking this schedule, which lists the number of ships in port each day and how many passengers are on board.
Break plates (with permission)
People around me threw their plates with gusto, smashing them on the cobblestone patio and sending pottery shards flying into the air. Still, I hesitated. It seemed rude, both to break the plates and to launch them in the direction of the dancers having a merry time. I did let them fly eventually, and found that it was kind of fun to break something.
The plate-smashing is part of the White Door Theatro’s interactive play, “The Greek Wedding Show.” A recreation of a traditional wedding reception in the post-war 1940s, the play began indoors with introductions of the bride and groom and various family members. The action then moved outside to a courtyard, where we were shown to a private table laden with a selection of appetizers and a carafe of white wine.
The majority of the show featured lively music and dancing. Attendees are treated like guests and encouraged to take part in the festivities. In fact, it’s pretty much mandatory. The lovely cast members actively engaged audience members, drawing them into the action and demonstrating how to do the various dances. We spent more time on our feet than we did sitting down. Except when we needed a thirst-quenching drink of wine, our glasses topped up by the groom’s quirky Aunt Maria.
Explore ancient ruins
A massive volcanic eruption in the 17th century BC both devastated and preserved the city of Akrotiri. This remarkable site, which predates Pompeii, was once a bustling trading center, and a prosperous one as evidenced by the two- and three-story houses adorned with frescoes—all of which lay buried until excavation began in the 1960s. Fortunately, an absence of human remains means Akrotiri inhabitants likely abandoned the city before disaster struck.
See the pretty things removed from the ancient ruins
Akrotiri is kind of a tease. There are placards scattered around showing photos of colorful mosaics found in the various dwellings. We looked around for these pieces of art, wondering how the heck we could be missing them, when we were told they’re now housed at the Museum of Prehistoric Thira in the town of Fira. So that’s where we headed next to see a fresco depicting blue monkeys and other eye-catching artifacts.
Visit a red sand beach
Before or after the ruins at Akrotiri, take a ten-minute stroll to an unusual beach nearby. Reddish sand and cliffs the same color make for some dramatic scenery.
Stuff yourself on local cuisine
Moussaka. Grilled prawns and sea bass. Stuffed vine leaves. We’ve already mentioned how delicious the food is in Santorini, and here are some restaurant suggestions. Our hands-down favorite was Dionysos, which was recommended to us by a friend, and specifically the dish “Pork Fillet Santorini”—grilled pork on a bed of pureed fava beans and accented with sundried tomatoes and capers. We also liked Theoni’s Kitchen in Fira and Taverna Simos in Firostefani, the next village over, both of which completed the meals with desserts on the house. And for stellar Greek salads we recommend the ones at Fira’s Meat Corner Grill. Their gyros are tasty, too.
Sample the local brew
The donkey is the unofficial symbol of Santorini, its adorably sad-eyed visage adorning everything from tote bags to bottles of beer from the Santorini Brewing Company. Of the Brewing Co’s three different varieties, we tried Crazy Donkey, touted as the first and only IPA produced in Greece. We bought a large bottle at a shop in Fira and took it back to our hotel to enjoy on the terrace overlooking the sea. We give the beer two hooves up.
Watch a sunset…or a moonrise
We thought our eyes were playing tricks on us. A few minutes after the sun set one evening, it seemed as if it reversed course and was popping back up over the horizon out to sea. Too much Crazy Donkey? Nope, just the first and only fiery moonrise we’ve seen.
Everywhere Once 
My friend is going to santorini soon, I’ll show her this
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where did you stay?
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Hi, Hilde. We stayed at the lovely, family-run Hotel Thira. The property overlooks the sea (non-caldera side) and is a short walk from the center of Fira. In early May, a double room cost $57/night.
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Don’t forget the fabulous little bookstore in Oia – Atlantis Books! So cute and great little history there.
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Enjoyed reading your article…Planing to visit Santorini sometime soon 🙂
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“..all of which was buried for millions of years until exacted in 1960’s”..
Artistic licrnse ? 😉
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Typo, it happens. 😉
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Nice! I want to go there!
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We only had a few days on Santorini 2010, as we looked back from the ferry, all 3 of us said it was the best, a place to visit again. I remember 1st night at the top, Korean newly weds asked me to take a photo for them, their backs out to the water. I did and walked on around the side of a restuarant to cablecar, then I looked at the buildings down the cliff, OH what a light picture, Where are the newlyweds,? I raced and found them, with hand signals and explanations, sent them to look at what `I had seen. Not every one would go where I did. It was great to see their faces about an hour later, coming up to thank me. Cique Terra North West Italy a similar feeling of wanting to return. Keep the photos coming Paul
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Very nice and informative post! Great photos too!
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Nice to travel there again with you. We spent 2 weeks there in late September 1987 to recover from SE Asia and India. Our tiny room perched on caldera hillside was $25/a nite. ..still a backpacker’s special. we had a very entertaining view of cruise ship passengers loaded onto donkeys. Beethoven and Bach played from some restaurant every evening at sunset. I must return to do that hike. But, Next time I’ll take a taxi from the port to Thira. I remember the bus , top loaded with ruck sacks, nearly tipping off a cliff. Thank you for sharing and jogging our memories.
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This post is awesome! I really need to go to Santorini ASAP and when I do, I have to do all of the things you listed here. 🙂
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Reblogged this on digger666.
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Wow Santorini is so beautiful!! Definitely gotta visit it someday.
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I wish I could hire you two as my travel agents to book my trips. Next year I’ll have enough money and unlimited time — it’s the planning that’s the overwhelming part for me. Great post as usual! Funny, I just went to the Thorn Tree Forum per your last post and saw a message from the Institute for the Study and Monitoring of Santorini Volcano (IMPIS) sent to Santorini hotels to warn their guests of dangerous landslide conditions at Akrotiri’s Red Beach.They are warning people not to go down to the beach and may have to erect a fence.
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