Why the Greek island I’d always avoided is now one of my favorites

Nov 14, 2021

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Greece ticks every box for my ideal summer vacation: It’s easy to get to, has excellent weather, there are beautiful sandy beaches and genuine, warm hospitality. It’s affordable, and the food is delicious.

There are endless Greek islands to explore and my strategy has been to try a new island each time I visit. I’ve enjoyed the likes of Mykonos, Crete, Paros, Corfu, Kos and more.

But the most famous island in Greece had stayed firmly off my to-do list. At least, until now.

Sure, Santorini might be well-known for its spectacular sunsets, dreamy ocean views from high atop cliffs, and for being the perfect honeymoon destination. But, whenever I personally thought of Santorini, the negatives were always the first thing that came to mind.

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(Photo by Benjamin Smithson/The Points Guy)

I worried about the overwhelming cruise ships crowds, and the pushy influencers blocking space to take their perfect sunset selfie. Not to mention overpriced accommodations targeting honeymooners for more than $1,000 a night for a basic hotel room, and baking hot sun sapping my energy while traversing up and down hundreds of stairs each day.

I had easily found Greek perfection in so many other islands (Paros led the pack) with easy travel, few crowds and impressive affordability. So, why worry about Santorini?

A recent out-of-season trip to Greece to earn easy and affordable British Airways status had me thinking about which island to visit. I spent a few days on the island of Ios which was both amazing and frustrating as while there were zero crowds everywhere, but most amenities were closed.

After much research, I decided it was finally time to give Santorini a try. It was early October so I figured the crowds and cruise ships would largely have left for the season.

Santorini’s accommodation prices are largely seasonal and were significantly cheaper in October than they had been in July or August. I chose a Hyatt Small Luxury Hotels property and found a great deal at On The Rocks, located in the small village of Imerovigli.

Related: Romance is not dead: A review of On The Rocks, Hyatt’s Small Luxury Hotels in Santorini, Greece

(Photo by Benjamin Smithson/The Points Guy)

I caught the ferry from Ios to Santorini and as the famous island’s ferry port came into view, the first signs were not good. Hundreds of tourists were swarming the port, all attempting to maneuver large amounts of luggage around the limited space and uneven surfaces. As the ferry docked, the staff screamed at us to get off as quickly as possible, so they could keep their port stop short.

Once on the dock, there were no obvious signs or paths explaining where to go, and there was an atmosphere of absolute chaos. I was starting to regret my decision and considered jumping right back on the ferry. I could also see two large cruise ships docked at the island, and I imagined encountering thousands of day-trippers swarming into Santorini at that very moment.

Related: These are the best times to visit Greece

Once I arrived at the hotel, though, it was a completely different story. The property was incredible, from the breathtaking views to the hardworking staff and the swimming pool cleverly built right into the side of a cliff. It was an oasis of peace and calm and I felt immediately relaxed. The hotel was reasonably full, but in the village of Imerovigli in October, there were very few other tourists around.

(Photo by Benjamin Smithson/The Points Guy)

The sunsets right from the hotel weren’t bad either.

(Photo by Benjamin Smithson/The Points Guy)

I could have happily stayed at the resort my entire time in Santorini, but I had one more obstacle to overcome: braving the chaos of Oia to witness those world-famous sunsets over the blue church domes.

In October, I needn’t have worried. There were some people around and the most popular viewpoints were full of people holding a favorable spot to watch the sun go down, but it was nothing like I feared it would be. Virtually no selfie-sticks, the cruise ships had gone and though a very diverse crowd of people from all over the world remained, everyone was pleasant and respectful.

Oia, Santorini at sunset (Photo by Benjamin Smithson/The Points Guy)

It wasn’t the most spectacular sunset I’ve ever seen in my time, but I’m glad I got to experience it. There are plenty of stairs to face in Santorini but the weather was mild enough that I wasn’t wiped out from sunstroke.

After the sun went down it was an easy, well-organized bus ride back to Thira (near Imerovigli) for a cheap and cheerful seafood dinner at a local taverna before wandering back to the hotel.

The key to enjoying Santorini for me was being strategic about my visit. If I was to travel there during the summer peak periods I would have undoubtedly had a different experience. Even visiting in the months of May and September in the shoulder season would still have resulted in more crowds and higher prices.

Related: 11 things I wish I knew before visiting Greece

For me, I think October was the perfect time to visit (as I imagine May would also be for many, as it’s outside of peak season but still fairly warm). Accommodation prices dropped considerably at this time of year, and while it wasn’t a ghost town like Ios was, there were just enough people to provide genuine atmosphere, without it feeling crowded or unpleasant.

Choosing to stay in an area far away from Oia was also a good idea. It was peaceful in and around my hotel, but I could still head into (and out of) Oia whenever I pleased.

And the weather was absolutely perfect too, around 75 degrees Fahrenheit and sunny each day; perfect for topping up my tan before returning to face a long, cold U.K. winter.

Greece upgraded many of its airports during the COVID-19 pandemic and Santorini Airport (JTR) is new, modern and very easy to use.

(Photo by Benjamin Smithson/The Points Guy)

Bottom line

I thoroughly enjoyed my October visit to Santorini and it’s now one of my favorite Greek islands.

I visited alone, and my wonderful hotel was so romantic I’d love to return there with my partner next year. While I still would never dream of visiting in peak summer, if you are strategic about it you can experience the very best Santorini has to offer in the shoulder season.

I now fully “get” the magic of the place that attracts people from all over the world. I’ve seen a lot of ocean views in my travels and those endless caldera panoramas from high up the cliffs on Santorini are among the best.

There are plenty of Greek islands you don’t need to do any research or preparation to enjoy; just arrive and relax. Santorini definitely takes some planning, but it’s well worth the effort if you have the flexibility to avoid the crowds, heat and high prices.

Featured image by Ben Smithson / The Points Guy

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