Easy to Moderate
Difficulty Level

swimmingfood and wineHikingChurches-monasteriesArchaeological sitesHorseback ridingSailing

Cyclades Islands Multi-Activity Adventure

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.

Additional information

Tour paceModerate
Suitable forAll travelers, Couples, Families, Solo
Comfort levelSuperior

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

meals Dinner       accommodation 3* Hotel in Naxos


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.

meals Breakfast, Lunch                accommodation 3* Hotel in Naxos


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.

meals Breakfast                 accommodation 3* Hotel in Naxos


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, cooking class etc. are optional activities. You may consult your tour leader for options, prices and availability.

meals Breakfast          accommodation 3* Hotel in Santorini


Day 5: Hiking from Fira to Oia & Sunset Sailing Cruise

Today, we will take the scenic hiking trail from Fira to Oia, all the way along the Caldera cliff edge. It is an easy, approximately 3.5-hour hike, passing through Firostefani, Imerovigli and Skaros, offering spectacular views over the caldera and culminates in the charming settlement of Oia. Upon reaching 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 roof top terraces offering breathtaking caldera views, where you can enjoy your lunch.

Hike duration: 3.5 – 4 hours | Distance: 9 km | Level of difficulty: easy to moderate

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!

meals Breakfast, BBQ Dinner     accommodation 3* hotel in Santorini


Day 6: Santorini South Discovery

Today we will enjoy a fantastic day in Santorini as we explore the natural and historical wonders of the south! In the morning, our first stop is the traditional village of Pyrgos, a designated “protected settlement” since 1955. Pyrgos, a typical Fortress Settlement of the Cyclades islands, boasts the ruins of Kasteli Castle atop its hill – one of the island’s five ‘kasteli castles’. We then ascend to the monastery of Prophet Elias, offering 360 panoramic views of the island. A breathtaking but slightly rough descent trail leads us to the archaeological site of Ancient Thera, perched at 360m height on Messavouno mountain. Inhabited since the 9th century, it was named after the mythical king of the island, Theras.

From there, we will follow the descending hiking path to Perissa, where you will have free for relaxation, lunch, swimming, water sports, scuba diving or a walk along the long black sandy beaches of Perissa and Perivolos.

Continuing south, our next destination is the archaeological site of Akrotiri, also known as the “Greek Pompeii”. This prehistoric settlement, a significant Bronze Age site, unveils unique findings, two-story buildings and houses.

*For sea kayaking enthusiasts, we can offer an alternative adventure instead of visiting Perivolos beach. Starting from Akrotiri, embark on an unforgettable experience, paddling by the Red and White beaches, exploring the south coast of the island in an extraordinary way. This adventure includes views of spectacular rock formations, swimming, snorkeling in crystal-clear waters, visits to beautiful beaches, and a light picnic – all part of this amazing adventure!

meals Breakfast                  accommodation3* hotel in Santorini


Day 7: Santorini - Athens

This is the last day of our weekly adventure in the Cyclades islands. The morning is yours to explore Fira town, purchase any souvenirs you may want or enjoy an optional activity of your choice before we board the ferry back to Athens.

meals Breakfast        accommodation  Depends on your schedule

What is included:
Trails Beyond tour leader for the whole trip, local guides & activity instructors.
6 days of accommodation in 3* hotels, based on double occupancy (for 4* accommodation, please contact us).
All meals, as indicated on the trip notes (6 breakfasts, 1 lunch, 2 dinners).
All Ferry tickets (Athens to Naxos, Naxos to Santorini and Santorini to Athens), economy class.
All necessary ground transfers on the islands.
Entrance fees to sites listed in the tour itinerary.
Cost for all activities included in the tour program (1 sailing cruise, 4 hiking & 1 walking tours and 1 wine tour).
All taxes.

What is not included :

International airfares.
Travel insurance.
Transfers to/from Athens airports and to/from Piraeus port.
Any meals not specified in the itinerary.
Any beverages or alcoholic drinks during meals.
Optional activities that are not included in the day-to-day itinerary.
Other expenses of personal nature and tips.

Scheduled departures 2024

Departs on Price / person + Own room
26 March ‘24 1.590 € 250 €
14 April ‘24 1.590 € 250 €
12 May ‘24 1.590 € 250 €
22 September ‘24 1.700 € 280 €
13 October ‘24 1.590 € 250 €

*There is a minimum of 4 participants for the tour to depart

Prices 2024 for private groups:

Price per person
Low season Medium season High season
For 2-3 guests 2.350 € 2.460 € 2.620 €
For 4-5 guests 1.750 € 1.850 € 2.030 €
For 6-7 guests 1.570 € 1.670 € 1.830 €
For 8-9 guests 1.460 € 1.560 € 1.700 €
For 10-16 guests 1.400 € 1.470 € 1.650 €
Single Supplement 250 € 280 € 370 €
Low season: April, May & October

Medium season: June & September 16th -30th

High season: July, August & September 1st – 15th


*10% Discount for children up to 11 years old

Please read carefully our Booking Terms & Conditions.

Tour Reviews

4.75/5 based on 4 reviews
January 11, 2016

We wanted to spend our holidays in the Cyclades islands but we were looking for someone to show us the secret paths, beyond the tourism masses. And so did Danae! We really enjoyed our time in Naxos and Santorini, 2 very beautiful islands, and especially the hiking trails both islands, the daily sailing cruise to Small Cyclades and the wine tour in Santorini. If you ever want to discover the Greek islands off the beaten track, do it with Trails Beyond!

December 13, 2019

It was a fantastic experience and Danae was very good. There was a one day general transport strike during our stay and she was able to sort out other transport for us and was very professional. Thought accommodation in Santorini could have been a bit better. But overall great.

December 13, 2019

Hi Debbie, thank you for your wonderful words! I am glad you enjoyed your holiday with Trails Beyond and I truly hope we get to see each other some time soon, it was a great pleasure to meet you and travel with you guys!! Regards, Danae

April 19, 2023

On behalf of us all, I just wanted to thank you so much for an amazing trip!

Everything from the accommodations, transportation and logistics was without a hitch. But the best part was the tours and meeting the guides, they were all so professional and kind. We got to understand the Greek culture and traditions at a personal level and it made the trip all the more enjoyable.

Thank you again! Erica, Courtney, Greta and Claire!

April 19, 2023

Hi ladies,

So great to hear from you and I am so happy you enjoyed your holiday in Greece with us!
The best reward is to have satisfied and happy travelers 🙂
Historical guides in Greece are indeed very professional and knowledgeable, glad you appreciated it!
I also hope you got a glimpse of the Greek Easter celebrations, which are very traditional 🙂

I hope you had a safe flight back home!

Warm regards,

July 16, 2024

Overall, very good tour. Super friendly and patient tour guide, mediocre hotel at Naxos, fine hotel at Santorini. The itinerary was well defined, flexible and interesting. The highlight of the trip was the day with the boat tour. Totally recommended.

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