Cyclades Islands Adventure: Trekking, Sailing, and Wine Tasting

Early in the morning, we meet at Piraeus port, where you will be welcomed by your tour leader! We board the ferry to Naxos island, the largest of the Cyclades islands (approx. 5 hrs by ferry).  Upon arrival and check-in at the hotel, you will have free time to relax at your hotel, spend some time at the beach or enjoy a cup of coffee in one of the front side cafes.
In the afternoon, we will enjoy a welcome tour of Naxos town (Chora).  We will visit the Venetian castle and the old town, while our guide will give us a good insight into the history and culture of the island.  Before dinner, when the sun goes down, we will not miss the chance to walk through the paved footpath towards the islet of Palatia and admire the impressive marble gate of Portara and the stunning sunset views it offers. In the evening, we will enjoy a welcome dinner on our first day altogether!

Enjoy a good breakfast today, as we will explore hiking the best of Naxos inland, with its fertile valley, olive groves, vineyards, and traditional villages.
Starting from the village of Moni, crossing old marble paths, and the Tragea plateau, we will end up in the picturesque village of Chalki after approx. 3.5 hours and we’ll visit the traditional citrus distillery, where we will be able to sample their famous locally produced liqueurs.
After lunch, we will visit the picturesque villages of Filoti and Apeiranthos, the most well – known and traditional villages of mountainous Naxos.
Hike duration: 3.5 – 4 hours | Distance: 6.5 km | Level of difficulty: easy to moderate

Today we will set off on a daily sailing tour with destination Iraklia and Schinousa islands, two secluded earthly paradises in the Aegean Sea that will captivate you for their crystal clear, turquoise waters and their calmness! A day full of surprises, fun, and adventure! Snorkeling, diving with a sea scooter, kayaking and much more will definitely give you an unforgettable experience!

Nobody can resist the charm of the never-ending, golden Naxos beaches and its clean, greenish-blue waters. You can explore some of them on a horse ride*!  Depending on the season and the weather, we will also have plenty of time to enjoy swimming and snorkeling in the crystal clear waters of the Aegean Sea. Alternatively, you can enjoy your last morning in Naxos leisurely, go to Chora for shopping or simply walk around the narrow alleys and enjoy your coffee in one of the charming cafes across the side front.
In the afternoon, we will take the ferry to Santorini. Prepare yourself for this striking, magical, volcanic island and feel its unique and inspiring aura! The views from the boat once we enter the caldera are simply stunning and captivating…
Our first day in Santorini includes a wine tasting experience of signature local wines and a walk around the capital city of the island, Fira.
*Horseback riding/ mountain biking are optional activities. You may consult your tour leader for options, prices, and availability.

Today we will take the hiking trail that leads from Fira to Oia, all the way along the Caldera cliff edge. It is a scenic route with no particular difficulties, offering spectacular views over the caldera. Passing by Firostefani, Imerovigli, and Skaros, we will finally reach the picturesque settlement of Oia in approx. 3 hours. Once in the picturesque village of Oia, you will have free time to walk around its picturesque streets, visit the tiny beautiful shops or relax in one of the numerous cafes/restaurants with rooftop terraces offering fantastic caldera views and enjoy your lunch.
Later on, we’ll follow the steps down to Ammoudi Bay, where we’ll board a beautiful catamaran yacht and enjoy a memorable sailing cruise inside the caldera. You will have the chance to swim in the Hot Springs, discover more of Santorini’s beauties, and enjoy BBQ dinner onboard, prepared by the crew.  On top of that, you will enjoy Oia’s famous sunset right from the deck!
Hike duration: 3 – 4 hours | Distance: 9 km | Level of difficulty: easy to moderate

Today we will enjoy a fantastic day in Santorini, discovering the natural and historical beauty of the south! In the morning, we will first visit the traditional village of Pyrgos, which was declared a “protected settlement” in 1955. Pyrgos is a typical Fortress Settlement of the Cyclades islands and on its hilltop, you can find ruins of Kasteli Castle, one of the five ‘Castelli castles’ on the island. We will afterward head towards the monastery of Prophet Elias, located on the highest hill of Santorini, offering 360 panoramic views of the island! From there a breathtaking, yet slightly rough, the descending trail begins that will take us to the archaeological site of Ancient Thera. Located at 360m height, on Messavouno mountain, it was named after the mythical king of the island, Theras, and was inhabited since the 9th BC century.
From there, we will follow the descending hiking path towards Perissa. Once there, you will have free time to relax, enjoy swimming, water sports, scuba diving, or a walk along the long black sandy beaches of Perissa and Perivolos and lunch in one of the seaside restaurants.
We will afterward head south and visit the archaeological site of Akrotiri, also known as the “Greek Pompeii”, one of the most important prehistoric settlements of the Aegean*. Unique findings, two-story prehistoric buildings, and houses, dated back to the Bronze Age, will definitely amaze you!
*For those of you who love sea kayak, we can arrange an unforgettable sea kayak experience, instead of visiting Perivolos beach. Starting from Akrotiri, you will paddle by the Red and White beaches, discovering the south coast of the island beyond the ordinary way! Views of the spectacular rock formations, swimming and snorkeling in crystal waters, beautiful beaches and a light picnic are all part of this amazing adventure!

This is the last day of our weekly adventure in the Cyclades islands. You have the morning free to explore the town of Fira, purchase any souvenirs you may want before we take the ferry back to Athens.