SantoriniPicture a pool of sapphire sea ringed with peaks of pure black, red, and chalk white. Then top those cliffs with a huddle of brilliant white buildings mirroring the shapes of the landscape in stucco walls and arches capped with blue domes reflecting the color of the sea. It’s a description that can only describe one place– Santorini. Images of those blue domes litter the Internet, begging you to stop whatever you are doing, forget wherever you thought you wanted to go, and dream for a bit of Santorini. Scour the web and you can find articles telling you the exact best spots from which to watch the island’s famous sunsets. You’ll find tips about getting to the red beach and the white beach and tips for which of the vast array of tiny eateries overlooking the sea serve the freshest fish.

It is billed as the destination of a lifetime. But is it really? Here is what you really need to know.

The Santorini you really need to know

It’s hard to get there. Flight times average twenty hours or more at a cost of around $1,500 each way. There are a handful of lengthier options with multiple hops that cost less, but plan to spend a full day of your trip to get there and a full day getting back.

It’s expensive. Hotels are often in the $500 per night territory in peak season from June to late September. Meals are pricey, as you would expect on any island. And anything with that famous view comes with a premium.

Santorini shopping

Santorini shopping involves rubbing shoulders– literally.

It’s crowded. Really crowded. Think shoulder-to-shoulder everywhere you go. Roughly half a million tourists visit the crescent-shaped island each year, most crammed into the summer season. I visited in October and still felt cramped by the numbers of people. And to make matters worse, during the high season, cruise ships arrive almost every day, dumping thousands of additional tourists onto the island.

The top Santorini attractions and whether or not they are worth your time:

The Cave Hotels

Pluses: They are adorably small, unlike anything you will find anywhere else in the world. The views are spectacular, the proprietors charming.

Minuses: The hotels are squeezed in among shops, restaurants, and private dwellings, all connected by a maze of narrow cobblestone paths and staircases full of other tourists. Remember that shoulder-to-shoulder thing I mentioned?  The first problem is dragging your bags to the hotel from wherever it is you found to park your rental car, or where ever you were dropped by a taxi. The second problem is getting back out through the crowd when you want to shop or eat. The most concerning problem though is the gawkers. Those lovely terraces and pools you see in hotel photos can be seen by every tourist who wanders the walkways looking for their perfect sunset watching spot.

The Views and Sunsets

Pluses: They are stunning. There is no question about that. They are everything you thought they would be except…

Minuses: you will share them with thousands of other people, all looking for the perfect Santorini image to capture with their selfie stick. Be prepared for photo bombers, stairs, and lots of “Keep Off” signs on those lovely white arches.

The Wineries

Pluses: Like most everything else on the island, they have incredible views.Santorini wineries

Minuses: The wine is just average. There are crowds and stairs and the staff are often weary of the busloads of tasters that pass through the facility, especially on cruise ship days.

The Hiking Trail From Fira to Oia

Pluses: The scenic trail connecting the two main towns on the island makes staying in Fira rather than Oia more fun. Fira is slightly less crowded allowing you to venture to Oia and face the hoards only when you choose– like on the one day of your stay without a cruise ship in port. The views from the trail are exactly what you see on the Internet; they are why you came here in the first place.

Minuses: There are still hills and stairs to overcome to get anywhere. This island is not for anyone with mobility issues, or even weak legs.

Akritori Archeological Site

Pluses: It is an amazing archeological site– this is Greece after all.

Minuses: It is not an escape from the crowds, but then, this is Greece after all.

Scuba and Snorkeling

Pluses: It’s Santorini, right? The water is crystal clear and you get to have the bragging rights of enjoying the Aegean Sea like few others do. Above all, a boat trip gets you away from the masses of people on the island.

Minuses: Don’t come here looking for spectacular sea life. There are fish, but in fewer numbers than you would see in the Caribbean. But at least you can escape the crowds


Pluses: The fun thing here in the high season is celebrity spotting. Katy Perry, Brad Pitt, Angelina Joli, and Tom Hanks have reportedly been spotted in past seasons.

Minuses: Expect rocky beaches, not fine sugary sand, and of course, the ever present hills, stairs, and crowds.


Pluses: Most shoppers come here looking for local art and jewelry. The choices are extraordinary– enough to fill an extra suitcase with.

Minuses: Choose wisely and ask questions. Not all you see in the shops is locally produced. And did we mention the crowds and stairs? Hawkers are not a big problem, but in the areas closest to the stairs down to the cruise port, shop keepers do become a bit more aggressive than on the lesser-traveled paths.

Karavolades Stairs from Fira to the Old Port

Santorini donkeys

There will be poo!

Plus: Whether you go by donkey or on your own two feet, you will have a story to tell and amazing photos to prove it.

Minuses: There will be poo. Lots of poo. Smelly donkey poo. The donkeys themselves are known to be somewhat contrary, which means they may bump walls, fellow donkeys, or people walking the staircase. Taking the tram rather than the stairs is an option worth considering unless you really like donkeys. And stairs.

If I haven’t burst your bubble and you are still Santorini dreaming I can’t blame you. It is a beautiful place.

Santorini tram

All of the scenery and none of the poo.

Recommendations to make it a better trip:

Go in April, May, or late September, not mid-summer. My October trip was slightly chilly and breezy, but pleasant. The heat of summer would have made the crowds and stairs almost unbearable.

Stay in Fira, not Oia. A search for hotels in Fira for an April stay found numerous choices like the Anteliz, starting just over $200 per night. Similar rooms in Oia, like this one at Adronis Luxury Suites push closer to the $400 mark for the same time period.

Consider a cruise. There will always be cruise ports that leave you wanting more than a day to fully enjoy everything. Unless you love crowds of fellow tourists, Santorini sadly, does not fall into that category. I sailed on the Silver Spirit by Silver Sea and found a day in port to be quite adequate. I drank in the beauty of the place, then left it comfortable in the knowledge that there are far quieter destinations to enjoy the culture of the Greek Islands.

As much as you may picture yourself lounging by the pool on the terrace of your cave hotel looking out at the spectacular colors of the caldera at sunset, trust me when I say that the sunsets from the balcony of a cruise suite as it sails toward the next amazing port are just as lovely.