Part 3 of 4: Adventures in Greece
Day 1: Arriving in Imerovigili and The Rock of Skaros
September 2018. We arrived at the Port of Athinios in Santorini after a 2.5 hour speed ferry from Milos ready for exploring sunny Santorini. Wow! What a crowded port! Instantly I missed Milos, because it was so quiet and peaceful there. The drive to our hotel, along a steep narrow winding road had me nervous, as did the busy traffic of Fira and Imerovigli. I told my husband I wondered if we should have just stayed in Milos.
Astra Suites

It really didn’t take long to reach our hotel, Astra Suites located in Imerovigli. To our surprise, staff members were at the curbside to greet us! Not only that, but the staff slung our bags onto their shoulders and carried the bags as not to ruin the wheels! We followed their lead, down stairs that seemed to turn here and there like a maze. Despite the fast paced walk down the steps, I was in awe of the beautiful blue and white buildings built on and into the cliff.
The concierge was at the entrance greeting us and offering fresh cold lemonade. The opulence of Astra Suites left me speechless. To put it another way, this place was amazing! The concierge showed us to our accommodations and gave us a tour of the room. After that, he arranged a walking tour of the island for our last day, as well as a table reserved at the Astra Suite Restaurant for the evening. Even more amazing, our room was located adjacent to the infinity pool which overlooked the caldera and the majestic Rock of Skaros. Seriously, I had a hard time believing I was here because it was just unimaginable, in other words, I was filled with gratitude. For more information on Astra Suites follow this link to their home page. Astra Suites.









The Rock of Skaros
Barely settled in Santorini, we knew exactly where we wanted to go exploring first on this sunny day. We wanted to enjoy a bit of adventure and climb the rock in front of us! The Rock of Skaros was formed by a volcano thousands of years ago. In addition, a fortress was built around the rock in the 14th century. Also houses and buildings were built around the rock as well for protection from raiders. In the 18th century, earthquakes reduced the fortress to rubble and ruins. These ruins are still present today.
Climbing the Rock
As staff pointed the way, excited to explore, we followed their directions. To begin with, we were to start walking towards Fira. Next, we were to descend at a small church located beneath the restaurant with the red umbrellas. Once found, we were to pass the church, and descend down the path. Finally, follow the path to the top of The Rock of Skaros. Shockingly, we had no problem getting there, as described. Did I mention I love Greece? After passing the church, we walked down many steps towards the bottom of the Caldera, this was the easy part. In contrast, the way up took awhile. The path seemed to end towards the top because there was no particular pathway the last 20 feet or so. In other words, it was a vertical climb! For this reason, I did not climb to the top even though Steve did.
Path to Skaros Starts at this Church Looking up at Church Path to Top of Rock of Skaros View Half Way Up Ruin From the Fortress Cave Ruin Almost to the Top! Climbing the Last Few Feet View from Top of Skaros
Astra Suites and Astra Suites Restaurant
After exploring, a dip in the pool felt wonderful back at Astra Suites under the sunny Santorini sky. In fact, the tranquility of looking over the pools edge was priceless. Dinner was at the Astra Suite Restaurant. The Rock of Skaros was directly across from our outdoor table. In addition, the sun set over the caldera adding to the ambiance. Our wait staff was attentive, the food was marvelous, and our first dinner in Santorini was perfect.
Perfect Dinner Location Beautiful Sunset Sunset Bread and Flavored Butter Ancient Boar Shrimp

Day 2: Fira Town and Sailing Tour
We awoke early and enjoyed breakfast, especially since it was brought to our small private terrace. We were ready for exploring Santorini on this beat sunny day. Plans for the day included a 1.4 mile walk from Imerovigilo to the town of Fira and a sunset catamaran tour of the caldera. The path to Fira takes you up and down many steps, past churches, restaurants, hotels, shops and more. It is quite the workout!.
Town of Fira
Wandering around the narrow cobblestone streets you will see Greek culture in abundance. I enjoyed the sidewalk musicians. I asked a young accordion player if I could take his picture, shyly he smiled and nodded his head, yes. The blue steeples and domes of the churches were scattered around Fira. You will also find there are shops for everything. I bought a pair of leather sandals. Fira was busy, although not so crowded we couldn’t take pictures and enjoy a leisurely pace. We had a great time exploring this Santorini town. We were there early in the morning which helps avoid the cruise ship tourists.
St. Gerasimos Church, Firostefani, Santorini Windmill Street in Fira Shoe Shopping Upscale Fira Street St. John the Baptist Church at Fira Accordian Player Imerovigili

Sunset Sailing Tour
Next on our agenda was the Catamaran tour. Soon we were sailing over the turquoise waters of the Aegean Sea. We past the Red Beach and the White Beach. The crew skillfully sailed us around the tiny island of Nea Kameni, just off the Santorini shore. Still an active volcano and responsible for creating Santorini as it is today. The water is warmer here than the sea because of the volcano. I didn’t swim because it was too chilly for me, although Steve enjoyed a swim. The crew prepared a delicious dinner. It was quite the feast. We dined on pork, shrimp, chicken, and several side dishes. The fava was so yummy. We sailed out to sea to view the sunset. Unfortunately, the evening’s sky was a bit overcast. Regardless, viewing the sunset from sea was still spectacular. Our boat tour ended as the sun went down.






Day 3: Walking Tour and Fira

Venetian Castle
Today we were excited as we prepared to go on a walking tour exploring Santorini, complete with wine tasting! It was another sunny day! After another great breakfast on our terrace, we walked up the many steps to the road to meet the tour guide and 3 other tourist couples. Blue Shades of Greece was the name of the tour company with Billy as our guide. Billy was knowledgeable and we liked him immediately.
Pyrgos
First stop was the charming village of Pyrgos. Pyrgos is set inland Santorini and is a peaceful village immersed in culture. Remnants of it’s medieval past are scattered throughout the town. Pyrgos hosts one of the 5 Venetian Fortresses in Santorini, which is Kasteli Pyrgos. When you roam the streets of Pyrgos you will see authentic Greek culture, not the touristy culture you see in Fira. Because of this, it is much less crowded. Billy led us around to the sites in town. He then led us atop a hill where we awed at a panoramic view of the Aegean Sea and Fira in the distance. Interesting to note, in 1953 there was an earthquake which did considerable damage to several of the structures and homes. Sadly, some have never been repaired.







Akoritori
I was excited about the next stop since it was on our must see list. Akortori is an ancient Minoan Civilization. It also was covered by a volcanic eruption in the 16th century BC. Reminiscent of Pompeii, volcanic ash buried the city which preserved it. No human remains were found, unlike Pompeii, the people had some type of warning and evacuated. Excavation is still being performed. When you visit this ruin it is inside to protect the area. You are able to walk around platforms which overlook the ruins and excavation areas. You can also walk around on the ground floor amongst some of the ruins.
After viewing the ruins we took a short drive to the Black Beach and passed a tomato factory and museum. I can’t imagine what is in a tomato museum but I wish I would have had the chance to find out!
Akrotiri
AkrotiriAkrotiri Akrotiri Tomato Factory and Museum Black Beach
Megalochori
Megalochori, next on our agenda, was yet another picturesque village for exploring Santorini on this beautiful sunny day.. Quiet and traditional like Pyrgos, Megalochori, has it’s own distinctive charm. Like Pyrgos, it is located inland, furthermore, the countryside around the little village is rich with vineyards. Interestingly, the vineyards in Santorini do not grow upward on trellises. As a matter of fact, the grape vines are close to the ground. Since ancient times and continuing today, the vines are trained to grow close to the ground, in a circle, resembling a basket or bowl, subsequently, preserving water for the plant.





Venetsanos Winery
Speaking of grapes, next stop was the Venetsanos Winery. Located high on a cliff overlooking the sea, Venetsanos was a perfect place for a wine and food tasting. Five types of wine were sampled. My favorite was Mandilaria, which is a dry dark red wine with a fruity aftertaste. Generally speaking, all the wine was good. In addition, local food was paired perfectly with each sampling of wine. Varieties of cheese, fava, pork, grape leaves, and tomato fritters were served. Tomato fritters are a must try Santorini specialty. As a matter of fact, Steve does not like tomatoes yet he loved these fritters. In addition we enjoyed Fava, another Santorini special treat that has a distinctive Santorini taste.
Venetsanos Winery View from the Winery View from the Winery Tomato Fritters Local Meats, Fruits, and Cheese
Oia
Last stop, the beautiful, Oia. Billy expertly maneuvered us up steps and through alleys finding the best place to view the famous Oia Blue Domes. An iconic view also beautiful. Oia is similar to Fira, with shops and restaurants lined along the narrow cobblestone streets. How I would have loved to spend a few more hours in this fascinating town. I was wishing this was not our last day because I would have loved to visit Oia again.
We had never thought we would enjoy a walking tour as much as we enjoyed this one. That is to say, it was interesting and at each place we were able to get out and explore, we never felt rushed. Blue Shades of Greece showed us a comprehensive tour of Santorini and had us visiting places we would not have discovered on our own. Particularly, Billy was an amazing tour guide he helped make exploring Santorini on a sunny day even more perfect!







Back at Astra Suites we relaxed and watched the breathtaking sunset from our room and terrace. The sunset was spectacular which made us happy since it was our last night in Santorini. Supper was at Anogi, a restaurant recommended by our tour guide. Dinner was wonderful with souvlaki being my choice, whereas Steve chose shrimp. I selected a white wine which complemented my meal nicely.
Soulvlaki at Anogi Shrimp at Anogi
Fira
Steve wanted to walk back to Fira to buy a few T-shirts he had seen yesterday. I wasn’t fond of the idea because we had walked and climbed a lot of stairs today! Steve was going regardless, therefore, I tagged along. I was glad I did! Fira was vibrant at night. In essence, there was a festive atmosphere as the lights were bright, music could be heard from tavernas and restaurants, and many people were out and about. Steve found some T-shirts so we headed back. I was not enjoying the steps at all. Fortunately, a local had told Steve of a back way with less steps. He found the area and we followed the alley back to Imerovigli, as a result, I was much happier. Thus ended our last night in Santorini. We had a great time exploring sunny Santorini and can’t wait to return.

Resources:
Before any trip I take I do a lot of research to find the most information I can and plan for my best trip possible. I liked this book for Santorini because there are lot of tips and information I did not find elsewhere. I did not necessarily like the day by day itinerary, but the information was good and did help plan my itinerary.
For more on my trip to Athens and Greece you can follow these links:
https://thegenxtravels.com/2019/04/23/exploring-athens-greece-rainy-day/
https://thegenxtravels.com/2019/04/23/3-days-in-beautiful-milos-greece/
https://thegenxtravels.com/2019/04/28/5-best-beaches-to-explore-in-milos-greece/
https://thegenxtravels.com/2019/05/09/exploring-acropolis-parthenon/
Diary of a Gen-X recommendations for hotels and restaurants are based on our own experiences. We do not receive compensation for recommending at any of these nor are we affiliates of any hotels or restaurants. We only recommend restaurants that we have personally visited and we feel have great food and great service. The only hotels we recommend are again places we stayed which were clean, comfortable, and provided great hospitality.
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looks amazing everything, can t wait to go there in 25th of July ♥️
Have a wonderful trip!! I’ll be looking forward to your post on Santorini!
thank you very much ! and sure , i will share my experience in Santorini!
Love all the photos. Putting this on my travel bucket list.
I loved Santorini! We are returning in September to see the things we missed the first time!
Nice trip! I was there a week ago. I liked the way you visited Santorini and that you concentrated everything in few days: that’s how Santorini worths a visit, all at once.
I also liked how you tell us your experience even though I prefer sharing my feeling instead of being a real travel guide 🙂
Thank you. Santorini is so amazing!