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  • Writer's pictureSiri Kay Jostad

Santorini Greece: Travel Guide

Updated: Aug 19, 2020

If ever there were a place made for Instagram, it's Santorini

by Siri Kay Jostad

If you want to go straight to Where to Stay in Oia, go here

If you want to go straight to Where to Eat in Oia, go here

Social Media Is Impacting Santorini

Santorini is smaller than you might guess--it's just 35 minutes or so to drive end to end. This sets the island up for massive traffic issues during high season and when cruise ships dock because there is essentially a single road.

Locals refer to their island's 13 towns as "villages." We all know the island as Santorini, but locals don’t use that name for it. Santorini (Saint Irene) was so named by the Franks in 1200AD.

The real name for the island is Thira, named to honor a Spartan king.


(You may not realize it, but that roof is someone's home or business)

When I visited, I witnessed people blatantly disregard each other, as well as ignore the merchants and land owners, by boldly stepping over railings and other obvious barriers on to the roofs of buildings, and sneaking under ropes meant to ban entry, just in order to 'get' their pictures. When told to step back, I heard these people say things like ‘it’s ok…just one photo”. The locals don’t think it’s ‘ok’. One photo multiplied by thousands of individuals each day adds up. It’s wrong. People taking photos are very often trespassing. This is serious stuff. It's so serious and sad that locals have to paint on their rooftops warnings to stay off. I even saw one roof with with barbed wire laid over it. Please be sure, if you go, to get explicit permission to go on walls and roofs and down paths that lead to people's homes.

When you work with a Flytographer professional photographer, they actually get official permits to go where normal tourists are not allowed, so you get access to some special spots and you are doing so legally. Personally hopping under ropes while jealous tourists watched on hungrily made me feel like a celebrity. 😁

One poor old island native was charging tourists 1 euro to take photos with his donkey all fancied up. Sad donkey. We just gave him 2 euros for his effort. A lot of people took pictures without paying him which is a bit of a sin. I think it’s sort of weird for people to take a photo with a donkey they had no experience with…what's the memory they are preserving there?

Apparently, this old guy is a ‘pensioner’. We learned all about him from Veronica, our Concierge at Armani Luxury Villas. She was a wealth of information for every random question we had. Greece doesn’t have a social security system or a formal system for taking care of the retired elderly and selling photos with this donkey that he owns is his way of being an entrepreneur and supporting himself at the end of life.

Siri Kay Jostad of Wander Away with Siri Kay looking at a fancy donkey in Oia Santorini Greece
This is the dressed up donkey. Check out the crowds in the background to see what a normal day looks like during off-season (October!)

Get this fact:

The island has only had electricity since 1974!

Photography at its Best

This picturesque piece of rock with its dramatic cliffs, cascading to the bluest of seas, paired with stunning sunsets, bright white stone houses with blue church domed roofs is a stunningly epic backdrop for Instagram influencers. Today, everyone who goes to the island is attempting to capture the perfect's absolutely CRAZY to see and I am utterly amazed that anyone ever gets a shot without someone else in the background. We got up at 5am to meet our Flytographer photographer, Kimon, just after sunrise in order to get photos with just us in them. And we were amazed how many others were running around town at that early hour to do the same.

If you're not familiar with Flytographer, it's a community of photographers on every continent, that you can hire when you're traveling. You hire one for 30, 60, 90 or 120 minutes to take pictures of you on your vacation. It is truly the most amazing service. Me and my friend booked an hour and a half. Guarantees that you will come home with at least 30 professional (Read: good) photos from your trip. If you're a blogger, this is an invaluable resources for getting pics in case you don't have an 'Instagram husband" along for the ride.

They were kind enough to give me this code for you: FLY25 for $25 off your first booking with them.

Siri Kay Jostad of Wander Away with Siri Kay being photographed in Oia Santorini Greece by Flytographer Photographer Kimon
TBH: I never love myself in pictures...but getting a pro to take them means I will feel the best I can!

How to Avoid Cruise Ship Crowds

During season, which extends April 1 to October 31st, the island's 15,000 population swells to over 2 million people. This will matter to you when you visit. Most tourists arrive by cruise ship, docking in the capital town of Fira, so you will want to plan your daily activities around the influx of people.

There are lots of places on the web where you can get information about the docking schedules of cruise ships around the world. I use Crew Center because no matter where I am in the entire world, you can get detail about which cruise line, the exact ship, the port, the time of arrival and departure, the number of passengers and the number of crew. Seriously, this is SUCH valuable information.

On my recent visit to Santorini, this is how we used this information:

If a ship was arriving at 9am, we knew it would take buses until 10am to get to Oia. Most ships leave their passengers on-island until an hour past sunset, since that's what people come to Santorini for. On that day, we would do all our in-town shopping or eating, then leave the village for a hike or a lesser populated activity. If you read my blog about Rhodes, I share how great this advantage was and what exactly we did to avoid cruise ship crowds.

Blue Roof of Oia Santorini Greece

Why the Buildings in Santorini are Painted White

The magic visual of this island is the landscape of white structures, occasionally topped with azure blue. The obvious theory for why the buildings are all white is for their ability to deflect extreme heat. It also turns out that during times of cholera and the plague, a cheap disinfectant was lime whitewash, so covering houses with it was an effective way to contain the epidemics.

Siri Kay Jostad of Wander Away with Siri Kay posing in front of a blue roof in Oia Santorini Greece
Seriously loving my new aquamarine ring I'm wearing here that I bought in Athens just before landing in Santorini

What do the Blue Painted Roofs Mean?

It's often said that the blue and white colors represent the Greek flag and are supposed to be a gesture of patriotism begun during the Ottoman occupation when they were not allowed to fly their flag. Instead, they showed their patriotism by painting the villages the colors of the flag: blue and white.

Blue roofs belong to churches. The reason there are so many, is because most private properties have their own family chapels. I was told by a resident that many people erect chapels on their private property in order to take advantage of tax breaks and at one time, the offer of free electricity. So...aside from religious reasons, you can see there are other motivators for building a chapel at home.

Toilet Paper

It's an island with no natural water. They don’t flush the toilet paper…instead they put it in the trash can next to the toilet (and they ask you too as well!). Gross, right? Well...ya gotta live local.

Out of habit, I accidentally flushed mine twice in our villa. (sorry Armeni Luxury Villas)

Get a Porter on Santorini !

OMG, were we glad to have a porter. The concierge for our hotel offered to arrange his hire and he met our car at the post office where our driver dropped us. He literally put a 40 lb suitcase on his shoulder, a 10kg duffel over the other shoulder and hand carried the other 40 lb suitcase. (#betterthanadonkey) For that we tipped him 20 euros and it was well worth it.

See? Even this guy can't believe what our porter is carrying!

Since none of the streets in Santorini have names, we would have been super challenged to find our villa without his leading the way. He wound his way through the crowds of people and took us down steep stairs (that btw, we would never have wanted to navigate ourselves with heavy luggage in hand) right to our villa door. Be smart—tip well because you will need him to get you out of there at the end of your stay too.

Santorini Streets Have No Names

People use landmarks-- like turn left at the Poniros (jewelry store), then find the place with green stairs and there is the restaurant. Causes you to pay quite good attention 😁

Santorini Beaches

Because of its active volcanic history, the island has beaches with 3 colors of sand: red sand, black sand and white sand...which makes it kind of fun. Keep in mind, that the popular village of Oia (pronounced EEE-Uh) has no beach…just buildings built into and cascading down the steep cliffside towards the caldera

Views from Santorini

The views are everything you expect them to be and everything you've seen on Instagram.

There is something magical in the water of the caldera. I can’t explain it. It's mesmerizing.

The Oia Main Drag

We were advised not to go anywhere outside our villa for the hour before sunset because the main path in town is crowded like a line for a Disneyland ride. The first night, we doubted how bad it could be and decided to brave it anyway, thinking all would be fine if we headed the direction opposite of the best sunset views people clambered for. It was still like salmon swimming upstream. We had to keep ducking into shops to make any headway. Kinda not worth it.

Santorini Resources

Cruise ships dump thousands of people into this village on the daily. Typically 4 ships per day, but in high season up to 9 per day. Locals say the tourists are mostly Americans and Chinese. Not many Europeans. The feeling around town is that cruise ship visitors don’t really spend much money in the village, and from our perspective it looked like everyone was just taking photos. Resources on the island are imported, and water is difficult to come by. Villagers feel the cruisers take food and water from their boats and simply walk through town looking for photo ops. Not good for the local economy, except for the fees the Cruise Companies pay to the government to dock here. So many people you can’t drive easily which is a problem if you live or work on the island..

Local Life

It was interesting to learn that locals work 9 months a year with not a single day off—sometimes 12 hours per day because they are serving the tourist season. People need to earn a full year's living in those few months so they work their hineys off. Many people we spoke to then took these other 3 months to travel themselves, go visit family or just to go home and go to the beaches themselves.

Getting Around

There are only 33 taxi cabs on the island and no Uber.

Initially, I booked a rental car. We had places all over the island to visit. I was sorry to miss many of them in our 5 days, but when I got there and saw the vehicular chaos, I was SO relieved I didn't have a car. Instead I booked a private driver back and forth to the airport and called on them during our stay for any place we needed a ride--like when we walked the Oia to Fira trail and our tired feet wanted a ride home.

Here's the sitch:

There's no parking. Flat out. If you go to Oia, there's a postage stamp sized parking lot by the post office. Don't expect to find a spot. If we had flown in with our 40 lbs roller bags plus carry on, had to find a place to leave the car amongst the utter car chaos there at the entrance to Oia, then (lugging bags) attempt on our own to locate our would have been a frustrating mess. We saved our vacation by canceling the rental and ordering a driver.

Siri Kay Jostad of Wander Away with Siri Kay riding in the back of a car on Santorini Greece
Here I am a passenger, not a driver (thank goodness)

Booking rides in advance with private drivers is expensive. From the airport to Oia for a private ride is was 50 euros. For a shared ride with someone going the same direction, it would have been 40 euros for the two of us.

If you're not staying in Oia, then it will be easier to have a car. If you want neither car, nor private driver, there are those 33 taxis (fat chance) and there is a slow bus system. It can be done.

This is the lovely 3-villa complex where we stayed 4 nights. The concierge, Veronica, was top notch. She is as good as you would get at a 5-star hotel. Veronica spent time explaining and sharing everything we could ever want to know and need for our stay. For check-in, she sat with us in the living room of our air conditioned villa so that by the end, we felt like we’d made a friend. You can read more about this and other places to stay in Santorini here.

All 3 villas at Armeni are unique. Our Grand Family Suite (Glafki) was huge. It felt like we had checked into a small home. Two big bedrooms, 2 big bathrooms, a TV (which we never used), Living room, a kitchen with oven, stove, sink, dishwasher, frig and our fave…a hot water kettle. The frigerator acts as a mini bar but they gave us 2 bottles of ice cold water and a bottle of wine on check in as gratitude for choosing them. The electric kettle was our friend every night when we made tea. .A humidifier keeps the cave hotel from ever getting musty. The indoor dining table is where I caught up on email and wrote blog notes. The private patio behind our own locking gate with views of the caldera, housed our private jacuzzi and the outdoor dining table where we took our breakfast each morning (included in the booking price)


We were close to the main path of Oia and yet far from the madding crowd above. Quiet and private, just how I like it. Apparently celebrities do too because they frequently rent all 3 villas at once for family, security and staff.

In a cliffside town with hotels built into caves, wifi is a constant challenge everywhere in Oia. Signals struggle to penetrate all that rock. In our villa, the wifi was good but it was best out on the patio...which is where we should be anyway, not on our devices. Despite the wifi struggle, my friend, Vaishali, who teaches live language learning classes on Sundays, even when we travel, had wifi good enough to connect for 2.5 hours of problem.

Bathrobes and towels were provided.

To read about the yummy, worth-visiting places we ate in Oia, click here

Shops In Oia Worth Stopping For

Charm and quirk ooze from every corner of this now-famous book and art shop. When you're browsing books, look up. Secret loft beds, hidden amongst the books are where the founders used to live and sleep in the early days of the store. One was our host (a darling young Irish man who looked like a California surfer). He spent oodles of time gently helping us pick out an ancient Greek philosophy book. Along with that, I bought two

Greek poetry books. The outside roof of the shop is open to all. Sale books are on open shelves for 5 euros up there, some couches and sun cover, plus a really great view and photo spot. They welcome anyone who wants to come up to lounge or take pictures…which many were doing.

Antique Store (so sorry I can't remember the name!)

It was located on the same side of the trail as Poniros Jewelry store a few stores closer to the Oia castle, if that helps you locate it. We found all kinds of treasures we loved in here and came home with some antique coins. I fell in love with some handmade rugs here too.

The Evil Eye

The Greek Evil Eye is literally everywhere and on everything you can image in every single store. I bought some small necklace charms and a glasswork evil eye I brought home for my mom. The traditional dates back to the 6th Century BC and the symbol is meant to ward off the curse of an evil eye shold someone cast that upon you.

Hike From Fira to Oia

To avoid the cruise-shippers on one of the days of our visit, we got up early to walk the famous 'path' between Oia and Fira, the island's capital. Our concierge let us know that the first part of the 'path' from Oia was actually just along the main road sharing space with cars and ATV rentals (no thank you!). She advised we hire a driver to drop us at the place where the 'path' diverges towards Imerovigli on the dirt, which we did and were glad of it.

You'll note that I keep putting the word 'path' in quotations. This is because we had this vision of some flat pastoral path meandering through meadow-like areas high above the coast. Well it ain't none of that!

Check out this video I took at the start of our walk. haha

Siri Kay Jostad of Wander Away with Siri Kay at a church on the path between Oia and Fira Santorini
The first 'site' on the hike/path is this 500 year old church (great photo opp)

To read all about our adventures on the trail along with some ideas how to maximize the experience, read this post.

The hike ends in Fira. We didn’t eat in Fira even though we met our driver for the ride back home in front of the McDonalds.

If you want to know about the amazing places where we ate in Oia, read about them here.

The Oia Castle

The Oia Castle is the ruins from which everyone pilgrimages at the end of each day to sit and watch the famous Santorini sunset. One afternoon, we walked towards the castle with intentions to take steps down to Ammoudi Bay. Bad timing…sunset was upon us. Since no cruise ship was in, the crowd was lighter, but people lined up early to scope seats on the castle wall.

We came upon these hairbands tied on railings…what are they for?

The walk down the stairs to Ammoudi Bay smelled like urine. We understood why when we saw that donkeys walk the trail.

At the bottom of the steps, Sunsets Restaurant was the reward. We'd already had dinner so opted for dessert. We had best Baklava ever paired with a classic Santorini sunset view.

The Donkey 'Taxi'

At the bottom of the 250 stairs back up, a man offers you a donkey 'taxi' to ride up for the bargain price of 6 euros. He had a line of takers, including some pretty big men. Halfway up, walking, I understood the need. I mean it was a heart pumping, body sweating, heavy breathing trek. Once again, we'd inadvertently embarked on this trek wearing inappropriate footwear and found ourselves divesting our flip flops. We found that the leather of them was slippery on the stone and offered no protection for the cobbled road.

Bare feet meant we were dodging donkey dung all the way up. Our timing totally sucked. The green flash of sunset hit just as we neared the top and hundreds of humans poured on to the path, slowing us to a stop. The magic of a local man playing accordian player made it all tolerable and a wee bit magical. Got home, washed feet, plopped in the private hot tub of our villa.


The whole Canaves brand is very confusing. There are six different Canaves resorts on Santorini and it takes a genius to determine the differences. Luckily only one has a spa. The spa is at the Canaves Oia Suites which is at the ‘end’ or ‘bottom’ of the island at the end of the path through town.

Whenever I travel a spa treatment is in order.

Here we indulged in an Indian head massage and goat milk hair mask ritual paired with a foot and leg massage, which turned out to be a wonderful full body massage with the hair treatment. Canaves is uber upscale, fancy and formal. You are definitely being ‘served’. Got the requisite paper panties option which we find is the case all over Europe. Canaves was expensive but the experience was top notch.

Inner Island flights

I flew Business Class from the US to Greece, which meant my airline allowed me 70lbs in a single piece of luggage. Turns out, that leaves you at a disadvantage if you also need to take flights between Athens and any of the islands where airlines like Volotea, Olympic and Aegean only allow a single bag weighing 20-23kg (40 to 45 lbs) PLUS they also sometimes limit the total weight your carry ons can be (in the instance of Volotea, you are limited to 10kg of weight between your backpack, purse or anything else you bring into the cabin).

When I got tired of buying a cheap new suitcase every time I traveled abroad in order to bring back my purchases, only to donate it once unpacked at home, I got smart and bought 2 REI nylon duffles. They fold up into themselves to form a zippered pouch no bigger than a pocket. These have been life savers. In the instance of the inner island flights, I just repacked some of my big suitcase into my small duffle to carry on and in the end the Volotea rep just checked it free anyway. Good karma!

Note:. Don’t film inside the Santorini airport…the security guards don’t like that. I found out the hard way and deleted my video whilst she watched!



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