7.5.2026
The first thing I learned in Santorini? You’ve absolutely got to go with the flow. When my husband and I visited in June 2015, we were swept up in everything from donkey paths to red, black, and white beaches, ancient ruins, and cliffside views that didn’t feel real.
If you decide you too need this out-of-this-world experience, here are my top tips to help make your stay more enjoyable:
Plan to lug your suitcases on cobbled streets.
Like other areas in Europe, some roads are pedestrian only and if you’ve booked a hotel on one of those, your taxi driver will drop you off nearby and you’ll need to haul your suitcases around on the cobblestones and use Google Maps or some other service to locate and reach your destination. Our hotel wasn’t even on a pedestrian-only street, yet our taxi driver still dropped us off “nearby.” Thankfully, our hotel contact sent a small vehicle to rescue us and deliver us curbside (crisis averted).
Skip the Oia sunset.
Although it supposedly has the best sunset views on the island, we planned to watch a sunset from here and bailed. The marble walkways were gorgeous but slick, and with the shoulder‑to‑shoulder crowds, we spent more time trying not to get jostled about than enjoying the view. I’ve read it’s worse now with the number of cruise ships that visit the island. We drove back to Thira/Fira (where we stayed) and found the sunsets there spectacular as well.
Know whether the beach you are visiting is organized or unorganized.
Organized beaches tend to be in front of restaurants in the main areas of the cities. The loungers are free to use all day if you order food or drinks from the restaurant and consume it on the beach. (We misheard a kind gentleman explaining this and thought he said consummate it on the beach, which briefly horrified us before we realized what he meant — and then we couldn’t stop laughing.) Unlike the US, at the organized beaches the drinks are served in glass, you’ll get glass plates, real silverware, and cloth napkins. Although just as nice, unorganized beaches don’t have loungers or restrooms, and the trash might be overflowing, so you’ll need to plan accordingly. We treated our visits to unorganized beaches as “no trace” experiences and took our trash back with us to the hotel.
The caldera is jaw-dropping!
We didn’t have a ton of money when we visited, so we couldn’t afford to stay in one of the hotels on the caldera. Instead, we frequented the restaurants there for gorgeous sunset dinners and stunning breakfast sights. We also took advantage of the many public walkways along the caldera to get as much time looking at the views as we could. Note: I even used the public walkways for some morning runs, though I had to watch my footing so I wouldn’t faceplant on the ancient steps.
Rent an ATV and drive around without a plan.
The island is only so big so you can’t get too lost! Stop and enjoy the moment – let the island set the pace. That’s a huge part of the charm of this beautiful gem! The first day we took ours out, we accidentally wound up at the top of Mount Profitis Ilias, the island’s highest point. One wrong turn led to a sweeping view of the Aegean and a quiet monastery we hadn’t even planned to visit.
In Closing,
Santorini is one of those rare places that rewards anyone willing to wander. Skip the crowds, chase the views, taste everything, and don’t be afraid to take a wrong turn — it might lead you somewhere unforgettable. If you go, I hope these tips help you spend less time stressing and more time soaking in that Aegean-blue bliss, the kind that stays long after you’ve left the island behind.