Easy to Moderate
Difficulty Level

swimmingfood and wineHikingChurches-monasteriesArchaeological sitesHorseback ridingSailing

Cyclades islands Multi-Activity Adventure

When you think about Greece, the first things that come to your mind are white – cub houses, deep blue crystal clear waters, sandy beaches and sun? Are you looking for an unforgettable summer getaway with an authentic touch of culture and adventure? If the answer is yes, then this is the right exploration for you!

Join us to explore the hidden side of the Cyclades islands… go hiking in ancient paths, kayaking inside Santorini’s caldera, sailing or horseback riding among Naxos’ white sand beaches, go for wine testing, visit traditional villages and Venetian castles, monasteries and important archaeological sites, taste some delicious Greek food and of course, meet the local people and immerse yourself in their slow pace way of life!

Whether you are a couple, group of friends, solo traveler or family, this exploration is ideal if you want to enjoy a unique holiday experience in the Aegean Sea, beyond the beaten path

Our Cyclades islands multi-activity adventure is also available as a private trip. Take your own bunch of friends or family, choose your travel dates and leave the rest on us!

Tour Highlights

  • Explore the largest of the Cyclades islands, Naxos
  • Explore on foot Venetian castles and traditional villages
  • Visit a traditional citrus distillery in Naxos and sample their famous locally produced liqueurs
  • Sail, swim, dive and snorkel in the turquoise waters of Naxos’ coastline on a daily sailing cruise
  • Enjoy the worldwide renown sunset in Oia, Santorini
  • Discover the archaeological site of Akrotiri, also known as the “Greek Pompeii”
  • Sail inside Santorini’s caldera and swim in the hot springs!
  • Take a wine tour and taste the marvelous Santorini wines
  • Hike alongside the caldera in Santorini and enjoy the striking views it offers!

Additional information

Tour paceModerate
Suitable forAll travelers
Comfort levelSuperior

Day 1: Athens – Naxos

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 walking tour in Naxos town (Chora).  We will visit the Venetian castle and the old town, while your guide will give you a first insight on 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 during our first day all together!

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

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. From Chora, we will transfer to Kurunochori village, which is the starting point of today’s hike. Passing by small, traditional villages (Mili, Ano and Kato Potamia), you will have the chance to visit two beautiful Kouros statues lying there since the ancient times, as well as an abandoned Jesuits monastery, a secret gem of Naxos! Our hike ends at Melanes village, where you will enjoy lunch in a traditional family run taverna.

Next stop is a visit of the picturesque village of Chalki with the traditional citrus distillery, where you can sample their famous locally produced liqueurs.

Return to Chora later in the afternoon, evening free to enjoy Naxos the way you wish.

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

meals Breakfast, Lunch                accommodation 3* Hotel in Naxos


Day 3: Day Sailing around Naxos and/or Small Cyclades

Today we will set off on a daily sailing cruise and explore the hidden gems of Naxos’ coastline. Depending on the weather, we will sail either north or south of the island and/or possibly to the Small Cyclades. Turquoise crystal clear waters and secluded beaches, sandy anchorages and stunning seascapes are waiting for you! A day full of surprises, fun and adventure! Swimming, snorkeling, diving from the boat, local delicacies and much more will give you an unforgettable experience!

meals Breakfast, Light Lunch                    accommodation 3* Hotel in Naxos


Day 4: Naxos - Santorini

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.

Nobody can resist the charm of the never-ending, golden sandy Naxos beaches and its clean, greenish blue waters. You will have this morning free to spend it the way you wish before we depart for Santorini. You can choose among a fantastic horse-riding tour, a cooking class, a bike tour or simply wonder around the narrow streets of Chora, purchase local products and souvenirs or relax on the beach.

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. Santorini is a worldwide acclaimed wine destination, so don’t miss the chance to taste some local varieties! For the kids, we can offer fresh juice or refreshments.

*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 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. 3.5 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 roof top 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 on board, prepared by the crew.  On top of that, you will enjoy Oia’s famous sunset right from the deck!

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

meals Breakfast, BBQ Dinner     accommodation 3* hotel in Santorini


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 as 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 ‘kasteli castles’ on the island. We will afterwards ascend 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 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 afterwards 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-storey 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!

meals Breakfast                  accommodation3* hotel in Santorini


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, purchase any souvenirs you may want, before we take 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, 2 lunches, 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 (2 sailing cruises, 3 hiking & 1 walking tour, 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 2021 & 2022 

Departs on Price / person + Own room
29 May ‘21 1.390 € 220 €
19 September ‘21 1.390 € 220 €
17 October ‘21 1.280 € 170 €
10 April ‘22 1.280 € 170 €
14 May ‘22 1.390 € 220 €
17 September ‘22 1.390 € 220 €
8 October ‘22 1.280 € 170 €

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

Prices 2021 – 2022 for private groups:

Price per person
Low season Medium season High season
For 2-3 guests 2,000 € 2,180 € 2,350 €
For 4-5 guests 1,475 € 1,560 € 1,720 €
For 6-7 guests 1,275 € 1,370 € 1,530 €
For 8-9 guests 1,215 € 1,285 € 1,415 €
For 10-16 guests 1,150 € 1,240 € 1,300 €
Single Supplement 170 € 220 € 270 €
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 Updated Flexible Terms & Conditions.

Travel safe – Learn more about our enhanced safety measures.

Tour Reviews

4.5/5 based on 2 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

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