July 2016 – 4 nights with extended family
Santorini is easily what makes the Greek islands so famous. The picturesque whitewashed houses, blue-roofed churches, and old windmills set against the deep blue sea are the backdrop for one of the most romantic places on earth.
Like the rest of our travel guides, this is not an all-encompassing account of everything we did. We do not want to make a list of ‘Best’ or ‘Must-do’ experiences since we know it depends on your personal preferences. These are only our personal favorites and they are divided into two groups: “Avventura Favves” and “Other Things We Liked”.
The Avventura’s Greek Islands Map

Overview

A massive volcanic eruption in 1646 BC created this uniquely shaped island that formed from the edge of the caldera of the volcano. Standing at the highest point in the center of the island (330 meters above sea level) allows for some of the most astounding views in the world.
Despite the fact that the summer months in Santorini can bring in 15,000 cruise passengers a day, we found it easy to stay away from the crowds. There are three main villages (Fira, Oia, and Imerovigli) on the island and they each have their own vibe. We picked a cozy cave hotel nestled into the cliff near the quiet village of Imerovigli and enjoyed a perfect view overlooking the Caldera. We swam in the hotel pool and ate a delicious breakfast of fresh fruits and vegetables served to us on our balcony. The local tomatoes are so sweet and are the best we’ve ever eaten.
Because we felt like it was the right thing to do, we did squeeze in some culture at the archaeological dig of Akrotiri, which was part of the Minoan civilization and possible inspiration for the lost city of Atlantis. However, more appropriately, we focused our time on visiting wineries, beaches, and eating delicious traditional greek cuisine and fish, while enjoying perfect sunsets from many places throughout the island.
Avventura Favves

Perissa Black Sand Beach – Definitely make a stop at this beach to experience the unique black volcanic sand of this long beach with plenty of space to spread out the crowds. There are lots of beach bars lining the back of this beach and they all have their own sunbed service. It’s quite comfortable to order a juice or a small snack and spend the day relaxing on the sunbeds.




Venetsanos Winery – This small family-run winery gives a personal tour of their underground cellars with all of its unique architectural aspects. The family used to pump grape juice directly to the port below to be shipped to wineries to use for their own production, but we’re very happy that they realized it’s much better to just make the wine themselves. They are making some of the best white wines in the world from the Greek grape called assyrtiko. It has an incredibly rich flavor balanced with the minerality you would expect from the black rock volcanic soil. We bought a few bottles to bring home, but we wish we could have brought more. Although it can be found in the States, it is easily twice the price.
To Psaraki – This taverna is off the beaten path and is worth the drive to the southern part of the island. It has a long string of tables lining the coast offering every table an incredible sunset view. They serve up fish-focused classic greek dishes. Greeks love kids, which is part of what makes it such a great family destination. So while the adults had drinks and coffee, the kids played in the yard of the family that owns the restaurant since the restaurant and their home are one and the same.






Nomokis Villas (images above) – This is definitely one of our favorite hotels of all-time. It’s a cozy hotel with rooms cut out of the rock nestled into the edge of a cliff. They had a small pool, hot tub, and bar area, and served a delicious breakfast directly to our room with some of the freshest fruits and vegetables we have ever eaten. It was tranquility at its best.
Red Sand Beach – This rocky beach at the base of huge dramatic red cliffs produce the most crystal clear water. The kids loved snorkeling here and swimming out to the many rocks further off-shore. It’s a bit tricky to get to and requires some trekking over large rocks to round the corner.
PK Cocktail Bar – Some areas of Santorini are getting more of a nightclub vibe (like on Mykonos) and this cocktail bar is a good example of this. It’s not really our scene, but who doesn’t love craft cocktails artfully made with small tables overlooking the caldera?
Other Things We Liked


Santo Wines – This winery has a bit more of a touristic vibe than the family-run places we usually like to visit, and even though the guide seemed to be talking from a sheet he memorized it did give a lot of good information about their production and cellars. Even better, they offer lots of different options for combinations of wine tasting and snacks. We did the 18 wine tasting because, why not? The view was beautiful and the descriptions of the wines were good, but they did lack the personal service touch.


Ammoudi Fish Tavern – We spent the last night of our trip at this tavern with tables overlooking the marina below the village of Oia. It was a perfect spot to view the sunset, drink assyrtiko, and eat fresh whole fish. It would have been a favve if it were not so pricey. There are donkeys to take you up to town, but we felt bad for them, so some of us walked up the steep path and others took the car back to the town for ice cream.
Logistics and Miscellaneous Notes
- Santorini is very easy to get to in the summer months. Like all of the popular Greek Islands, there are many direct flights to the island from most of the major cities in Europe. The ferry service is also convenient. For this trip, we flew to Santorini after touring Athens and then took the ferry from Santorini onto another Greek island, Koufonisia.
- As we mentioned above, in the busy summer months, there can be up to 15,000 cruise ship passengers disembarking every day into the village of Fira. We chose to avoid this area entirely and would recommend the same to others.
- The best time to visit Santorini is in September. We would actually say this for visiting every Greek island. We had a blissful quiet week on the island of Skopelos in September 2019.
Next Time We Go
- We would stay again in the same area of the island (near Imerovigli) with the best views of the caldera. One can never get too much of that view.
- Drink more assyrtiko wine by visiting some of the other top-rated producers, Domaine Sigalas, Artemis Karamolegos, and Avantis Cellar Door. And this time make sure to ship plenty of wine home.
- Spend a day on a private boat that takes you to the white sand, red sand, and black sand beach in one day. We visited Santorini before we discovered just how much we love boat experiences.
- Go without the children, for the most romantic experience!
And just because we have more beautiful pictures…








