Santorini – The Second Time Around was Better Than the First

DAY 1:

Welcome to Santorini!  


The fast ferry from Mykonos is a quick 2 ½ hour ride. It makes one stop along the way in Paros and then off to Santorini. 

I must mention the organized way to board and disembark the ferry.  It goes like this………. The port of Mykonos, Tourlos, is 2 km north of Mykonos Town and this is where ferries from Piraeus, Rafina, and other islands arrive. Imagine 3 large commuter ferries and thousands of anxious travelers hanging around and waiting patiently for the ferry to arrive.  You can see it in the distance but if you can’t don’t worry, the passengers quickly head to the dock towing their luggage and whatever else they are taking with them. It’s a mad dash. 

The ferry docks and the gates open.  Some are getting off and some are getting on.  You only a few seconds to get on before the gate closes and the ferry departs.  Enter the cargo area and drop your luggage along with everyone else.  But remember where you drop it.  Because when the ride is over it’s the same mad dash down to find your luggage and disembark.  And if you can’t find it the fun begins.  

Just imagine climbing over baggage and pushing through the hoards who have successfully found their belongings and are ready to get off! It may sound like a horrifying experience but if you don’t ride the ferry you have not experienced Greece.  My clients got it.  I was seasoned at this.

Travel to Greece

As promised our driver was waiting for us which is another story.  Look for your name on a sign board.  Hopefully you have good eyesight and are a speed reader.  Because you have arrived at Athinios port and it may be more crowded than Tourlos in Mykonos.  Santorini hosts around 80,000 travelers per day during peak season, June – October.  Imagine all the people.  And that is why Santorini does get the reputation of being overcrowded with tourists.  But overcrowded or not it is a must see.

Santorini Sunsets

The volcanic island of stunning sunsets and dramatic views from Oia town is a major attraction because of its energy and mystery.  Famous for the strange white auberge (eggplant), the town of Thira and naturally its very own active volcano are what make this island a dream come true.  

Santorini is more romantic and much better suited to a honeymoon or couples’ vacation and those not looking to rock the house as they do in Mykonos.


Mystique, a Luxury Collection Hotel, Santorini

Last year we experienced the cave like rooms of Mystique, a luxury 5 star hotel. Awarded as one of the best hotels in the world it is carved into the rugged Caldera cliffs of Oia. Mystique overlooks the turquoise expanse of the Aegean Sea that encircles the island of Santorini. It’s iconic location on the lower side of the Caldera offers unobstructed, infinity views but take note, it is located on the lower side. 

Ooh the steps.  The 85+ steps in the heat can be challenging to say the least.  If you have problems with walking, balance, your knees your ankles or are not into a workout 5 times a day then do not choose a cliffside hotel.

Canaves Oia Epitome Santorini

This year I chose Canaves Oia Epitome for our accommodation. This 5-star luxury property is located in Oia but not built in the rugged Caldera cliffs like so many of the other luxury haunts. 

Perched above the picturesque fishing town of Ammoudi, the property is inspired by traditional Cycladic architecture, combining natural and earthy materials with modern design and style. Unique in that it is the only property on the island that offers both sea and sunset views from the privacy of each of the 24 luxury villas. 

You can still walk to town.  You will experience the finer things in life without having to climb hundreds of steps to get to and from your room, dinner, town…

Because we were 2 couples the room that suited us best was the Aqua Retreat Two Bedroom Pool Villa. It is luxury living at its best with two spacious living rooms, a Master bedroom with King Size bed and bathroom with rain shower, a second bedroom with King or twin beds, a wet area with rain shower and a separate bathtub. 

To round out its escapist feel, Aqua Retreat Villa features a unique see-through glass wall pool view from the lower level’s bedroom.  And if that wasn’t enough, a private garden with a hammock and a private terrace with an open air private heated swimming pool, as well as outdoor dining and sitting areas. 

The expansive view to the sunset, the Aegean Sea and Thirassia Island adds an extra level of indulgence. 

 Santorini, we have arrived.  It’s summertime and the livin is easy.

Dinner at Elements

That night we decided to enjoy dinner at Elements, the hotel’s restaurant.   We were greeted by Executive Chef Tasos Stefatos who walked us through the courses. 

It is a menu for the sophisticated – Modern European Cuisine meets Greek traditions.  My husband and I celebrated our anniversary on a candle lit terrace with impeccable sunset views surrounded by our friends.  It was truly a night to remember.

Day 2 in Santorini

The next day we would head to Ammoudi Bay to set sail on our own private 45ft Catamaran Sailing Yacht.  With Captain Kallisti and crew Babis, Tasos and Ioannis we were on our way to catch the sunset.  

It was time to swim in crystal clear fresh waters, admire the views of the Santorini Caldera, feel the power of the volcano and experience the benefits of swimming in its therapeutic waters.  Selfies and photo stops at the Lighthouse of Akrotiri and the intriguing Indian Face Mountain.

And then it was time for dinner.  Feta, tomatoes in the traditional Greek Salad, olives and olive oil, grilled beef and chicken, fresh fish and wine.  Opa! And the best is yet to be.  

Time to sail to the Old Port of Fira following the caldera coastline to the hidden church of Eftapedes, the bay of Armeni with the sun setting behind us. It is a Santorini Spectacle! And the night has come to an end.  Tomorrow is another day.

Day 3 in Santorini

Our last day in Santorini and how can you top last night.  Of course, with a private tour of the town with my favorite tour guide George.  He has promised a day to remember and off we go.

The most photographed and famous church with the blue dome in Firostefani.  “Firostefani” (Fira + Stefani, meaning crown in Greek) derives from its position on the highest part of Fira. Its gifted location on the caldera, on the north part of the island, makes it a remarkable sight.

Then off to another village Imerovigli and to the church of Prophet Elias, with a wonderful panoramic view.  The monastery of Prophet Elias, one of the oldest of the island. 3 kilometers away from Pyrgos village, is the highest settlement of Santorini and the only place you can have a bird’s eye view of the entire island.

Fira, Perivolos and Psaraki at Vlychada Marina

Fira, the beautiful capital of Santorini with its narrow streets is filled with inspired shops, relaxing cafés and exciting museums leading to picturesque neighborhoods that reveal the beauty of the town.

Off to Perivolos, one of the famous volcanic beaches of Santorini with black sand, deep clean waters, fully organized beach bars and taverns right on the seafront. 

George was hungry and so it was time for lunch. To Psaraki at Vlychada Marina, was created by its owners Thanasis and Aggeliki based on the idea of simple and honest food.  We met the owners and  chose our fish.  Simple and basic local products from the Santorinian land included cherry tomato, fava beans, capers, cucumbers, young green peas and white eggplant.  Simply delicious!

Santo, one of the finest wineries and most beautiful winery of the island is near Pyrgos. We got to taste local fresh crispy whites, captivating reds, old and rare, authentic and traditional and the opportunity to shop for some local products we simply could not do without.

Drinking wine and watching the sunset over the Caldera…… heaven on earth.

George saved the best for last as we headed to Akrotiri, a prehistoric settlement and one of the most important sites in the Aegean.  Once a Minoan port with connections to mainland Greece and as far as Egypt and Syria this ancient town is the actual town made of mud-brick.

Following a volcano, the town was covered in ash and has been preserved for centuries.  Akrotiri today is covered by a bioclimatic roof and walkways suspended above the archaeological remains.  We were able to walk down streets thousands of years old and see what the ancient city looked like.  It was an amazing experience. And now it was time to bid farewell to George. 

Adio.  See you next year.  Same time same place.

Tomorrow Santorini would be a memory, but the night was still young – Greeks don’t eat dinner until 11 PM.  We had plenty of time to head to Oia, one of the most photogenic towns with a maze of small shops, restaurants and cafes, almost all with spectacular views of the rest of the island and the caldera, and the remnants of a counter-culture community from back in the day when Oia actually was a quiet village.

The main street of Oia is anything but.  It is filled with tourists from all over the world.  It is fun, it is energetic, it is crowded but I wouldn’t miss it for the world.

All the healthy Greek eating gave us a craving for something Italian and Skiza did not disappoint.   A beautiful CAFÉ – PIZZERIA with two levels, outdoor and indoor seating, and a breathtaking volcano view. The pizza was excellent, and the gorgeous 180-degree view of the Aegean Sea left us in awe. 

Tired from a long day it was time to head back.  We knew the trip was close to coming to an end, so we needed to hang on to every second.  Tomorrow is another day and we’re still in Greece.

lisa crawford
Lisa Crawford

Luxury Travel Advisor, Founder, and CEO

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