7 Days in Santorini: My Actual Travel Journal (With Regrets)
I went to Santorini in late September expecting paradise. I got something more complicated — and honestly, better. Here's the unfiltered version.
Day 1: Arrival and Immediate Confusion
Flew into Thira airport (JTR) from on a 45-minute Sky Express flight that felt like riding in a school bus with wings. The airport is tiny — one baggage carousel, one cafe, and a wall of taxi drivers holding signs.
I'd pre-booked a hotel transfer (€25), which turned out to be wise because the KTEL bus to Fira costs just €2.50 but only comes every 45 minutes and the schedule posted online was wrong. Taxis are scarce. Don't count on finding one.
Checked into a caldera-view hotel in Fira and — okay, I'm going to be honest. That first moment walking onto the terrace and seeing the caldera drop 300 meters to the sea, with the white buildings cascading down the cliff and the sun making everything glow — I stood there for maybe ten minutes without moving. Some views live up to the photos. This one exceeded them.
Evening: walked the caldera-edge path from Fira to Firostefani (1 km, stunning, free). Found the iconic three blue domes. Dinner at Naoussa Taverna — one block back from the rim where prices are 50% lower. Grilled octopus, Greek salad, a carafe of house white. €22 per person. That octopus was grilled with the kind of simplicity that only works when the ingredient is perfect.
Day 2: The Hike That Destroyed My Feet
The Fira to Oia hike. Ten kilometers on a clifftop with the most absurd views I've ever encountered while walking. I started at 7:30AM from Fira, which was a good call — by 10AM the sun was relentless.
Things I didn't expect: some sections are genuinely rocky and require mild scrambling. My running shoes were fine but flip-flops would have been dangerous. I brought 2 liters of water and finished them. The path through Imerovigli is the most beautiful section — the Skaros Rock ruins jutting into the caldera like a broken tooth.
Arrived in Oia around 11:30AM, legs shaking, and descended the 300 steps to Ammoudi Bay for lunch. Ammoudi Fish Tavern served me grilled red snapper with lemon and olive oil on a table where waves lapped below my feet. €30 for fish, salad, and wine.
The climb back up those 300 steps in midday heat was the worst 15 minutes of my trip. My calves are writing this complaint.
Watched the famous Oia sunset from the castle ruins. Arrived 90 minutes early. It was... fine? The sun goes down, the crowd cheers, it's undeniably pretty. But honestly, I've had more moving sunsets in random places that weren't orchestrated. The crowd made it feel like a sporting event.
Bus back to Fira: €1.80. Last bus runs around 11PM. Get to the second bus stop in Oia for a better chance of getting on — the first stop fills the bus.
Day 3: Volcanic Beaches and Ancient Ruins
Picked up a rental ATV in Fira (€35/day from Zorzos). Drove cautiously because these Santorini roads are narrow, winding, and other tourists on ATVs drive like they're in a video game.
First stop: Akrotiri Archaeological Site. I wasn't expecting much and was completely wrong. Walking above a city that was buried in volcanic ash 3,600 years ago — with three-story buildings, pottery still in place, drainage systems — is eerie and wonderful. The covered walkway keeps you shaded. €12 entry, audio guide worth the extra €5. Closed Tuesdays.
Then Red Beach. The volcanic red cliffs are genuinely dramatic. The trail from the parking lot involves scrambling over loose rocks — proper shoes, not flip-flops. The beach itself is small and pebbly. Swam in the morning before wind picked up. Beautiful and uncomfortable in roughly equal measure.
Lunch at The Good Heart in Akrotiri village. Moussaka, stuffed tomatoes, village salad. €14 total. This is what Santorini tastes like when nobody's trying to impress tourists.
Afternoon at Perissa's black volcanic sand beach. Sunbed rental €8, a cold Mythos beer €5. The sand is bizarre — jet black and gets scorching hot in direct sun. Laid my towel down and the heat radiated through it. Spent three hours doing absolutely nothing.
Day 4: Sailing the Caldera
The catamaran cruise. €160 per person for the sunset option with Caldera Yachting. I debated whether this was worth it for weeks. It was.
Departed at 2PM from Vlychada port. Sailed to the volcanic hot springs — the water turns warm and sulfurous near the volcano. Important: wear a dark swimsuit. The minerals stain light colors. I watched a woman in a white bikini realize this too late. Bright yellow stains. She was not happy.
Swam at White Beach (accessible only by water), sailed past Red Beach, and anchored as the sun set behind the caldera. BBQ dinner on deck, unlimited wine and beer. The captain kept refilling my glass without asking.
The sunset from the water was genuinely better than from Oia. No crowds. Just the caldera turning orange and gold from sea level. I took exactly one photo and then put my phone away.
Day 5: Wine Education Day
Santo Wines winery — 5-wine tasting flight with caldera views for €15. The Assyrtiko hit me immediately: mineral, saline, with an acidity that cuts through everything. The volcanic soil creates flavors I've never tasted in any other white wine. The woman pouring explained that the vines are trained into basket shapes close to the ground because the wind would destroy traditional trellises. That fact made the wine taste better somehow.
Venetsanos Winery after — built into the caldera cliff. Tasting from €12. The Vinsanto dessert wine (sun-dried grapes, aged in oak) was the best dessert wine I've had outside of Sauternes. Bought a bottle for €40.
Explored Pyrgos village in the afternoon. This is the Santorini you don't see on Instagram. A medieval hilltop village with kasteli ruins at the top offering 360-degree views. Zero tourist shops, zero blue domes, just stone alleys and cats sleeping in doorways. I sat at the top for 30 minutes watching the island below and wondered why everyone fights for space in Oia when this place exists.
Dinner at Metaxi Mas in Exo Gonia. Tomatokeftedes (the cherry tomato fritters) and slow-cooked lamb with a local Assyrtiko. €28 per person. Reserve ahead — this place is popular for good reason.
Day 6: The Beach Day I Needed
I'd been going hard for five days. Day 6 was deliberate nothingness.
Late breakfast at the hotel. Took the bus to Kamari beach (€2 from Fira). Rented a sunbed (€8), read a book for three hours, swam twice, ate a gyro from a beachside place for €8. The black sand gets impossibly hot — I sprinted from my sunbed to the water like the ground was lava. Because it kind of was.
In the evening, walked to the open-air cinema in Kamari — Cine Kamari, €10. They showed a recent film in English under the stars with a bar selling cold beers. One of the most atmospheric cinema experiences I've ever had. The screen backdrop is the dark mountain and the sky full of stars.
Dinner at Ouzeri in Fira — meze restaurant on an outdoor terrace. Grilled sardines, zucchini fritters, crisp white wine. €22. Perfect.
Day 7: Sunrise, Departure, and the Thing I'll Remember
Woke up at 5:45AM and walked to Imerovigli for sunrise. I was completely alone. The east-facing side catches golden light that paints the caldera in colors I don't have words for. No crowd. No cheering. Just the Aegean and the sun and volcanic rock turning warm.
This was better than Oia sunset. By a lot. Not even close.
Final breakfast at a caldera cafe in Fira. Greek yogurt with honey, fresh orange juice, spanakopita. Watched cruise ships arriving below.
Transfer to JTR airport. Pre-booked, which you should always do — the airport is tiny and 1 hour before departure is sufficient.
Already booked for next October. But here are my regrets:
Should have done the catamaran cruise earlier in the trip, not day 4 — it sets the tone for the island better than anything else
Should have spent less time in Fira and more in Pyrgos
Should have bought three bottles of Vinsanto, not one
Should have skipped the Oia sunset crowd entirely and watched every sunset from Santo Wines instead
Santorini isn't perfect. It's expensive, overcrowded in spots, and the Oia hype machine is a bit much. But the caldera views are real, the wine is extraordinary, the volcanic beaches are unlike anywhere else, and sunrise from Imerovigli made me feel things I can't properly explain.
Pack a dark swimsuit. Book the early hike. Watch the sunrise, not the sunset. That's my Santorini.
