Cyclades islands multiactivity Adventure (7 days)

When you think about Greece, images of white – cubed houses, crystal clear deep blue waters, sandy beaches and abundant sunshine most likely come to your mind. Are you seeking an unforgettable island getaway infused with an authentic touch of culture and adventure? If the answer is yes, then this exploration is made for you!

Embark on a journey with us to uncover the hidden side of the Cyclades islands – go hiking in ancient paths, explore Santorini’s unique coastline via sea kayaking, ascend to the highest peak of the Cyclades, sail within Santorini’s caldera, indulge in wine tasting, discover traditional villages and Venetian castles, explore monasteries and important archaeological sites, taste delicious Greek food and, of course, connect with the local people, immersing yourself in their unhurried way of life.

Whether you are a couple, group of friends, solo traveler or family, this adventure is perfect for those seeking an active holiday in the Greek islands beyond the beaten paths.

Our Cyclades islands multi-activity adventure is also available as a private trip. Gather your own group of friends or family, select your preferred travel dates and leave the rest to us!

Tour Highlights

• Explore Naxos, the largest of the Cyclades islands.
• Hike to Mount Zas, the highest peak of the Cyclades.
• Explore on foot Venetian castles, ancient sites and traditional villages.
• Witness the renowned sunset in Oia, Santorini.
• Hike along the caldera in Santorini and sip in the spectacular views!
• Discover the archaeological site of Akrotiri, often referred to as the “Greek Pompeii”.
• Sail inside Santorini’s caldera and swim in the hot springs!
• Take a wine tour and savor the exquisite Santorinian wines.

Day 1: Athens – Naxos  (optional hike or welcome walking tour)

Early in the morning, we meet at Piraeus port, where you will be welcomed by your tour leader. Our journey starts as we board the ferry to Naxos island, the largest of the Cyclades (approx. 5 hrs by ferry). Upon arrival, you will have free time to enjoy lunch and a quick swim in the sea, if you like. Depending on the arrival time (according to the ferries timetable), this afternoon will feature either a hike to Chalki village or a welcome walking tour in Naxos town (Chora).

If the ferry schedule permits and the conditions allow for a more extended hike (also dependent on the season), you will be transferred to the beautiful village of Chalki. Once the commercial hub of the island, Chalki is nestled in the Tragea valley amid numerous olive groves. Our ascend towards the village of Moni, includes passing by several Byzantine churches, with Panagia Drosiani being the most renowned. Upon reaching Moni, you can enjoy the stunning view to the south and walk through orchards, olive groves, oaks and plane trees, before descending back to Chalki village. This is a loop-hike of easy difficulty.

Hike duration: approx. 3 hours | Distance: 8 km | Level of difficulty: easy to moderate

If the longer hike is not feasible today (due to late ferry arrival or limited daylight), we will instead enjoy an introductory walking tour in the Chora of Naxos. We will visit the Venetian castle and the old town, with your guide providing an initial insight into the island’s history and culture. As the sun sets, we will take a walk along the paved footpath towards the islet of Palatia, where we can admire the impressive marble gate of Portara and enjoy the stunning sunset views it offers. To conclude our first day together, we will gather for a welcome dinner in the evening.

Walking duration: 1 – 1.5 hours | Distance: 2 – 2.5 km | Level of difficulty: easy

Day 2: Naxos inland hiking: traditional villages & Kouros statues

Start your day with a hearty breakfast as we embark on a captivating inland hike across Naxos, featuring fertile valleys, olive groves, vineyards and traditional villages. Our journey begins with a transfer from Chora to Kurunochori village, the starting point of today’s hike. Passing through charming, small, traditional villages (Mili, Ano and Kato Potamia), you will have the opportunity to explore two beautiful, very well-preserved Kouros statues lying there since the ancient times, and an abandoned Jesuits monastery – an undiscovered gem of Naxos! Our hike concludes at Melanes village, where you will enjoy lunch in a traditional family run taverna.

Hike duration: 4.5 – 5 hours | Distance: 12 km | Level of difficulty: easy to moderate 

In the afternoon, we will visit the magnificent Temple of Demeter, near the village of Sangri. This beautiful temple, constructed during the 6th century BC, showcases the finest Naxian marble and is dedicated to the goddess of harvest and fertility.

Later in the afternoon, we return to Chora, and the evening is yours to enjoy Naxos as you wish.

Day 3: Hike to Mount Zas

Today’s hike is among the most popular hikes in Naxos, and we offer you two compelling reasons to embark on this adventure: a climb to the summit of Mt. Zas, the highest mountain in Naxos and all the Cycladic islands (1004 m), and an ascent to the mountain associated with the birth and upbringing of Zeus. Our journey starts in the village of Filoti, leading us up to the Agia Marina church. As we ascend the old footpath, we enter the Natura 2000 protected area, treating us to gorgeous panoramic views of the Aegean Sea and the neighboring islands. This circular trail takes us past the cave of Zeus, ending at Aria Spring.

Hike duration: 4 – 4.5 hours | Distance: 9.5 km | Level of difficulty: moderate | Elevation gain/loss: +580m/-580m

Following our descent from Mount Zas, you can enjoy lunch at one of the numerous local tavernas in Filoti. In the afternoon, depending on the hike we will have done the first day, we will either guide you on a walking tour in Naxos Chora (exploring the Venetian Castle and the Portara marble gate) or take you to the quaint village of Chalki, where we will visit a traditional citrus distillery and taste Kitron liquor, one of the local products Naxos is renowned for.

Day 4: Naxos - Santorini

Nobody can resist the allure of the never-ending, golden sandy beaches and pristine greenish blue waters of Naxos. This morning will be free to spent the way you wish before we depart for Santorini. Options abound – from a fantastic horse-riding tour, a cooking class, a bike tour or simply a leisurely walk around the narrow streets of Chora, shopping for local products and souvenirs or unwinding on the beach.

In the afternoon, we will board the ferry to Santorini, the striking and magical volcanic island with 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 features a wine tasting experience with signature local wines and a walk around the island’s capital, Fira. Santorini is a worldwide acclaimed wine destination, so don’t miss the perfect opportunity to savor some local varieties. For the younger participants, fresh juice or refreshments are available.

*Horseback riding/ mountain biking are optional activities. You may consult your tour leader for options, prices, and availability.

Day 5: Hiking from Fira to Oia & Sunset sailing cruise

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, we will descend the steps to Ammoudi bay, where we’ll board a beautiful catamaran yacht and for an unforgettable sailing cruise within the caldera. You will have the opportunity to swim in the Hot Springs, discover more of Santorini’s beauties and enjoy BBQ dinner prepared by the crew onboard. To top it off, you will witness Oia’s famous sunset right from the deck!

Hike duration: 3 – 4 hours | Distance: 9 km | Level of difficulty: easy to moderate

Day 6: Santorini South Discovery

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, 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 toward 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 kayaks, 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!

Day 7: Santorini - Athens

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