Greek Islands 2-3 Week Itinerary

Greek Islands 2-3 Week Itinerary

Is there a more spectacular destination in Europe than the Greek Islands?

For some time now I have found that something seems to be lacking when I go on my yearly “big” trip.

I began noticing this last fall when I was in Santorini, a startlingly beautiful Greek Island. I had planned our trip to the Greek Islands for months, leaving only minor items to last minute execution.

Santorini was the third stop on a trip through the islands of Greece over a course of about 3 weeks. My husband and I were celebrating our anniversary, so we wanted it to be perfect – maybe too perfect.

I organsied the whole trip independently and planned to travel by plane and boat, although you might also want to consider Greece tours which include most of the main Greek islands in the itineraries.

The places I had chosen to visit were off the beaten track enough that I felt a sense of adventure, with a bit of luxury thrown in for few days in Santorini. 

Here are the places I visited and where I recommend if you are looking for an authentic experience and have two to three weeks free to explore Greece.


1. Athens

Athens skyline

We flew in to Athens and spent one night at a hotel near the Acropolis. Athens is a really special city, with ancient ruins, temples, museums, cafes, restaurants, markets and so much more. Be sure to see all the main highlights which can be done in 2 days.

We then hopped on a small plane for the 20 minute flight to the magical island of Milos.  


2. Milos

Milos, Greece

Our three nights on Milos had the feeling we had found new family members we forgot we had; the people were so hospitable I thought I might be Greek and have a grandma on Milos I never knew existed.

The food was the best we had on our entire trip. We went on a sailing excursion and ate fresh fish caught by our captain prepared by the first mate. This was authentic Greece. 


3. Santorini 

Santorini, Greece

Santorini is one of the most famous islands in Greece.

For three days we had awakened to one of the most famous views in the world – the caldera of Santorini from Fira (or Thira).  The scores of donkeys passed by just below our terrace each morning, tethered together with bells on, they made their melodic descent, occasionally sneaking a bite of a restaurant’s greenery.  

We spent our days lounging by the pool sipping the cool white wine of the island overlooking the famous cliffs and many cruise ships that looked like toys coming in each morning just after dawn.  We scurried through the narrow walkways and shops that magically opened an hour before the cruisers made the trek up the gondola or on the backs of the little donkeys.  

Soon I started to feel a drain… I wondered how long I could keep up this sense of euphoria, traveling where I had planned for so long, experiencing things I had hoped to experience, it began to feel like a charade.

Everything was too blue, too white, too startlingly, achingly beautiful – and the people we encountered were all tourists, mostly there for just a few hours’ stopover from a cruise ship.  This added to feeling of unreality.

As I explored the coast of Santorini, seeing some of the most beautiful beaches in Europe, conversing with the “locals” (many of whom were from somewhere else; hardly anyone was actually Greek) I realized what was missing - something authentic.  


4. Syros

Siros, Greece

This stayed in the back of my mind as we boarded the ferry for our next stop, Syros.

Ermoupolis, Syros, I hoped, would take us out of the “tourist” zone and into the authentic daily life.  The capital of the island group of the Cyclades, Syros is a “year round” island, where whatever legal matters that need tending are done and therefore it doesn’t close down when the tourist season ends.

With streets paved in marble, competing churches on dual hilltops, its idyllic harbor and neoclassical buildings looking like a movie backdrop, it certainly was different than Santorini.  

Strangely we found more upscale food, at a place which seemed more out of Manhattan or San Francisco than anything you might find in Greece, with its cool vibe, blue back-lighting, decadent artistic foods, deconstructed traditional Greek entrees, it was like we walked out of an ancient world and into the future.

We did feel like tourists, but at least we were the minority, not the majority, of people we encountered. 

Everyone was still very friendly and almost everyone spoke English, but we were glad to be among people who greeted one another with a warm “Ya Sas” (Hello) or “Cali Mera” (good morning) instead of countless faces in a rush to purchase something and get back on their ship. I would recommend learning some basic Greek travel phrases to really impress the local people.

We rented a scooter (much to my dismay, my husband was determined to explore as the locals do) and rode to the opposite side of the island, discovering little beaches and empty harbors along the way.  


Why You Should Seek an Authentic Greece Experience

The trip was, by all accounts, exactly as I’d planned it.

The water was the most vibrant hue of sapphire, with the perfect amount of salinity and the right temperature to be both refreshing but not too cold with the perfect blend of adventure and relaxation.

The Greek Islands I experienced are now woven in to my being, an awareness that contributes to who I am.  But that is why I travel – to learn.  To learn about different people, experience new places, and sometimes even learn something about myself. 

Now when I go, I will look for the authentic, special places that the tourist hordes have yet to find.  For only then will I find the genuine inhabitants, engaged in their daily routine, and I will sit in silence and allow it to soak in.

I will remember the faces of the people, because I will talk with them, even for a short while.  Then I will have found what I was looking for – the authentic travel experience.