Last year, at the end of September, we spent three days in Santorini as a late-summer escape. The weather was still beautifully warm, but the crowds had thinned out significantly.

For a destination as popular as Santorini, that made all the difference. Instead of packed viewpoints and long waits (though, there were some exceptions- more below 🙂 ), we experienced the island in a much calmer, more relaxed way. It felt like the perfect opportunity to soak up the last bit of summer before the season officially came to an end.

In this travel guide, I’ll show you how we made the most of our three full days on the island: what we visited, how we got around, where we ate, and, most importantly if its worth paying Santorini a visit 🙂

1. Where we stayed in Santorini
2. Day 1 – Fira to Oia Hike
3. Day 2 – Boat trip
4. Day 3 Kamari & surroundings
5. Our favorite food spots in Santorini
6. Santorini – worth it or overhyped?

Where we stayed in Santorini

When it comes to choosing accommodation in Santorini, it really depends on your travel style, budget, and how you plan to get around the island.

The west coast is famous for its breathtaking sunset views, especially in places like Oia. However, it doesn’t offer direct beach access due to the steep cliffs. That’s why we decided to stay on the east side of the island, which is generally less touristy, more affordable, and much closer to the beaches.

During our stay, we based ourselves in Kamari, a relaxed seaside town on the east coast. We stayed at Mon Signor Boutique Hotel, and I can genuinely recommend it. The hotel was clean, beautifully located on a hill, and our room even had a private whirlpool on the balcony—perfect for unwinding after a day of exploring. Since we visited at the end of the season, the price was very reasonable. A similar stay with a caldera view in Oia would have easily cost double, if not more.

To get around, we rented a scooter, at Santoride – Rent a Moto which turned out to be the perfect choice. It gave us the flexibility to explore the entire island at our own pace. The owner was very kind and helpful and provided us with the best service.

If you’re not comfortable driving, there’s also a reliable public bus system connecting Kamari to Fira, where you can transfer to a bus to Oia. You’ll also see plenty of tourists renting quads, which can be a fun option. That said, they’re significantly more expensive, and since the roads on Santorini are in very good condition, a scooter is usually more than sufficient.

Day 1 – Fira to Oia Hike

On this day, we decided to do one of the island’s highlights: the hike from Fira to Oia. It turned out to be one of the most beautiful coastal hikes we’ve ever done. The views along the caldera were absolutely breathtaking and it was the perfect way to start the trip on an active note.

We drove our scooter from Kamari to Imerovigli, parked there, and started the walk. The hike took us 2 hours. Along the way, we stopped several times to soak in the incredible ocean views, admire some of the island’s most stunning luxury hotels, and—of course—pet a few of the many cats you’ll find all over Santorini.

We started the hike at 10:30 AM and reached Oia around 12:30 PM. By that time, it was already getting very hot, even though it was October.

If you’re visiting during the peak summer months, I’d highly recommend avoiding the midday heat. Instead, start early in the morning or go later in the afternoon to make the hike much more enjoyable. Make sure to bring sunscreen, sunglasses and a cap, as there’s very little shade along the trail. Also, avoid wearing sandals—the path can be uneven in parts. A good pair of sneakers or sports shoes will be much more comfortable and safer. It is also important to bring water but in case there is always the possibility to buy it along the way.

In German we say “Der Weg ist das Ziel”—the journey is the destination—and in this case, that couldn’t have been more true. For me, the hike itself was actually more beautiful than the destination, Oia.

I don’t want to be unfair: Oia is undeniably stunning. The whitewashed houses, the caldera views, and the iconic sunsets are all as beautiful as they look in pictures. But the overtourism—even in October—was honestly overwhelming. I can’t even imagine what it must be like in peak season in June or July. To be clear, the tourists themselves are not the issue, we were part of them too. What stood out more was the way the town felt staged in certain areas for certain type of influencers. There were terraces where you could rent dresses and take “Instagrammable” photos on swings, which made parts of the atmosphere feel a bit artificial and superficial.

We had originally planned to come back to Oia in the evening by scooter to watch the famous sunset from there. But after visiting at midday, we decided against returning and chose to watch the sunset somewhere else instead—which turned out to be a great decision (more on that below).

After lunch, we took the bus back to Fira and then walked back to our scooter in Imerovigli. While passing through Fira, we realised how beautiful the town actually is: vibrant, scenic, and noticeably less crowded than Oia. It’s definitely worth a visit!

Day 2 – Boat trip

Since we had already seen how beautiful Fira was the day before, we decided to head back to that side of the island to watch the sunset—this time from a Imerovigli viewpoint. It definitely did not disappoint. The views over the caldera were absolutely stunning, and we were lucky enough to catch one of the most beautiful sunsets of the entire trip.

Day 3 Kamari & surroundings

To unwind, we spent the afternoon at the beach, which was pleasantly quiet at this time of year. One thing worth noting: the beaches in Santorini are not sandy, but mostly made up of pebbles and volcanic rock.

Santorini isn’t your typical beach destination—it’s much more about exploring, landscapes, and unique experiences shaped by its volcanic origin. That said, there are plenty of other places in Greece if you’re looking for a classic sandy beach holiday. But Santorini stands out in its own, very unique way.

In the evening, we headed to the small village of Pyrgos, which turned out to be incredibly charming. With its narrow streets, traditional architecture, and a variety of small boutiques, it felt much more authentic and relaxed than some of the busier towns.We enjoyed some delicious moussaka at one of the best restaurants we visited during the trip (more on that below), which made it the perfect way to end our time in Santorini.

Our favorite food spots in Santorini

What would a trip be without some proper Greek food? The food in Santorini was absolutely delicious and definitely one of the highlights of our stay.

Here are some of our favorite spots:

Santorini – worth it or overhyped?

The honest answer is: a bit of both. Yes, certain parts like Oia, can feel overcrowded and overly staged at times. If you go in expecting a quiet, untouched paradise, you might be disappointed.

But if you approach Santorini the right way, it’s absolutely worth it. 🙂

There’s so much more to the island than the famous Instagram spots: breathtaking hikes along the caldera, hidden sunset viewpoints, charming villages like Pyrgos, and unforgettable experiences out on the water. We found that the magic of Santorini lies in exploring beyond the obvious and timing your visit well, especially in the shoulder season.

For us, it was the perfect mix of adventure, relaxation, and stunning scenery.And would we go again? Yes: but just like this: off-season, with a scooter, and always chasing the quieter corners of the island.

Happy exploring! 🙂