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8 Day Greece Itinerary: Athens, Milos, Santorini

Exploring Santorini

This 8 day Greece Itinerary is from our trip in September of 2018 which includes, Athens, Milos, and Santorini. It is a great itinerary for your first trip to Greece. We choose these areas because we felt we would get a good representation of what Greece was like.

Diary of a Gen-X recommendations for hotels, restaurants, activities or tour companies are based on our own experiences. We do not receive compensation for recommending at any of these nor are we affiliates of any hotels, restaurants, activities or tour companines.

Why We Picked Athens, Milos & Santorini for our Greece Itinerary

We choose Athens for the culture, famous Greek ruins, and for the Old European city life. In contrast, we chose the small island of Milos for more solitude, greek authenticity, small villages and towns, history and the many spectacular beaches. Lastly we chose Santorini for the experience of this famous island, the culture, and the beautiful towns built on the caldera.


Athens has many neighborhoods and we decided on the Plaka area because we could walk everywhere we wanted to explore. We wanted to see the Acropolis and Parthenon, Roman Forum and narrow old streets and shops. Comparatively, Plaka offered all of this within and more walking distance. Overall, we were very happy with this choice.


Milos turned out to be exactly what we wanted and more. Above all, very quiet and not at all busy or touristy. We decided to stay in Pollonia because it is a small village, very quiet and access to everywhere we wanted to go was a short jaunt and easy. Even though our hotel was outside of the village, it was just a short walk down the hill to Pollonia which had many delicious choices for dinner.


We chose Santorini because of the beauty of this island. At Santorini we elected to stay in Imerovigli. We decided on this area because it is right in front of the Rock of Skaros and we loved that view. Altogether, it turned out to be a very good choice with beautiful views of the caldera and amazing sunsets. Imerovigli is also less busy than Fira and Oia, therefore more quiet. which we liked. Imerovigli is also just a 30 minute walk from Fira and it is easy to hop on a bus to Oia. We were more than thrilled with this choice and it was absolutely perfect for us.

Greece Itinerary, Athens, Milos, Santorini

Fly Day


Day 1: Athens

For additional details, you can read more about our first day in Athens on my blog page Athens on a Rainy Day.


Day 2: Milos-Explore

Day 3: Milos-Boat Day

Day 4: Milos-Beach Day

For additional details click on my post, 5 Best Beaches in Milos. You can also read more about our time in Milos by clicking on my other post, 3 Perfect Days Exploring Milos.


Day 5: Santorini-Exploring

Day 6: Santorini-Fira Visit and Boat Day

Day 7: Santorini-Island Tour

  • Breakfast Astra Suites
  • Blue Shades of Greece Walking Tour of Island. All in all, I can’t say enough good things about this tour and the tour guide. To summarize, this is the best way to see Santorini’s highlights!
  • Pyrgos
  • Akortori
  • Megalachori
  • Venesantos Winery is set on the caldera. We had a nice assortment of wines to taste along with a generous assortment of meats, cheeses, fruits and Santorini favorites.
  • Oia is a city sitting on the caldera. Popular for it’s blue domed churches. Again, lots of steps, but that’s just Santorini!
  • Transfer back to Astra Suites.
  • Sunset swim at Astra Suites was a perfect way to relax after a big day of walking! In addition, beautiful sunset views.
  • Walk to Fira at night. Walking to Fira at night was as much fun as during the day. The town has a totally different exciting vibe.
The Lights of Fira

For more details you can click on my Santorini Trip blog page.


Day 8: Athens-Acropolis & Parthenon

Fly Day


I am big on planning and planning for a trip is always fun! It helps to have the right resources and if you use a travel agency using someone you trust is invaluable. When planning for our Greece Itinerary, I did a lot of research on line to determine we wanted to go to Athens, Milos and Santorini.

Travel Agent

We use True Trips Greece as our Travel Agent. They were highly recommended to us by one of my husbands associates. This group is awesome and they are located in Greece so know all the ins and outs. They arranged all of our hotels, transfers (car, local air and ferry) and some of our activities once we arrived in Greece for our entire itinerary in Athens, Milos and Santorini. From picking us up at the airport the first day to getting us back at the end, everything went smoothly. Everyone was prompt, courteous and had great information! We used there services for both our 2018 and 2019 trip. Currently we are working with them for our 2020 trip which may or may not happen! Regardless they have been there for us and are keeping us informed through this entire Covid mess. I can’t say enough good things about this group.

Internet Information

The Internet is a great place to get information but you need to make sure the sites are up to date and reputable. My favorite sites are as follows:

Guide Books and Maps

I absolutely love tour guide books and Maps. I think they have great information and are great to carry along. The following are my favorites that I have used when deciding what to do.


We had a wonderful first time in Greece! I hope my Greece Itinerary of Athens, Santorini and Milos is helpful and I tried to include helpful links both from my own blog site and other resources as well. I have included direct sites when possible for hotels and restaurants. We absolutely loved Greece and I will be coming out with another Itinerary over the next few months in reference to our 2019 trip which includes Athens, Crete and Santorini. Although we went to many of the same hotels and a couple of the same resturants there will be lots of new information and more places to discover!

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A Rainy Day in Athens, Sept 2018

3 Days in Milos, Sept 2018

5 Great Beaches in Milos, Sept 2018

First Time Guide-3 Days in Santorini, Sept 2018

Exploring the Acropolis and Parthenon, Sept 2018

Astra Suites Hotel, Santorini, Sept 2018, Oct 2019

To Read About our Other Greek Trip Click Below:

10 Days in Greece-Athens, Crete, Santorini-10 Day trip to Greece Sept/Oct 2019 Athens, Crete & Santorini