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Cyclades Islands Adventure


7 days


Arrival & Departures: Athens - International Airport Eleftherios Venizelos


Airplane, minivan & sailboat

Join us as we discover the undiscovered side of the Cyclades islands… Trek along ancient paths, kayak inside Santorini’s caldera, sail or go horseback riding along Naxos’ white-sand beaches, go wine tasting, visit traditional villages and Venetian castles, monasteries and important archaeological sites, sample some delicious Greek food, and, of course, meet the locals and immerse yourself in their slow-paced way of life!

Whether you are a couple, a group of friends, or a family, this expedition is great if you want to have an off-the-beaten-path experience in the Aegean Sea.

By Trip Tailors

This trip can be tailored to your needs. Fill out the contact form at the bottom of the page with the dates of your trip, your budget, the number of people, and anything else you think is important for us to take into account in order to send you a personalized proposal.

* Tour leader during the whole trip, local guides & activity instructors
* Accommodation for 3 nights in Naxos and 3 nights in Santorini in 3 * hotels
* All meals, as indicated on the trip notes (6 breakfasts, 2 dinners)
* All Ferry tickets (Athens to Naxos, Naxos to Santorini and Santorini to Athens)
* 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

* Air Tickets
* Travel insurances
* Accommodations in Athens
* 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 personal expenses and tips

Your steps


Athens - Naxos




Sailing Small Cyclades


Naxos - Santorini






Santorini - Athens


Athens - Naxos​

We will meet in Piraeus port early in the morning, where you will be greeted by your tour leader! We catch the ship to Naxos, the biggest of the Cyclades (approx. 5 hrs by ferry). After checking in, you will have free time to relax at your hotel, spend some time at the beach, or have a cup of coffee at one of the front side cafés. We shall have a welcome tour of Naxos town in the afternoon (Chora). We will tour the Venetian castle and the old town, and our guide will provide us with information about the island’s history and culture.

Meals included: Dinner
Accommodation: Naxos



Today, we’ll go through the greatest of Naxos’ inland scenery, including its rich valley, olive orchards, vineyards, and medieval towns.

Starting in the village of Moni and traveling along old marble routes and the Tragea plateau, we will arrive in the scenic village of Chalki after around 3.5 hours and visit the traditional citrus distillery, where we will be able to enjoy their famous locally manufactured liqueurs. Following lunch, we will visit the gorgeous villages of Filoti and Apeiranthos, two of the most well-known and traditional villages on the island of Naxos.

Hike duration: 3.5 – 4 hours | Distance: 6.5 km | Level of difficulty: easy to moderate
Meals included: Breakfast
Accommodation: Naxos


Sailing Small Cyclades

Today we will go on a daily sailing cruise to the islands of Iraklia and Schinoussa, two remote earthly paradises in the Aegean Sea that will fascinate you with their crystal clear, turquoise seas and peacefulness! A day packed with surprises, excitement, and adventure! Snorkeling, diving with a sea scooter, kayaking, and other activities will undoubtedly provide you with an amazing experience!

Meals included: Breakfast
Accommodation: Naxos


Naxos - Santorini

Nobody can resist the allure of Naxos’ endless golden beaches and their clear, greenish blue waves. Some of them may be explored on horseback*! We will also have plenty of opportunities to swim and snorkel in the crystal blue waters of the Aegean Sea, depending on the season and weather. Alternatively, you may spend your final morning in Naxos slowly, either shopping in Chora or simply strolling through the small lanes and sipping coffee in one of the wonderful cafés across the side front.

We’ll take the boat to Santorini in the afternoon. Prepare to be awestruck by this stunning, enchanting volcanic island and to be inspired by its one-of-a-kind energy! The views from the boat as we reach the caldera are just breathtaking and enthralling…

Our first day in Santorini includes wine tasting of characteristic local wines as well as a tour through the island’s main city, Fira.

Optional Activities: Horseback riding and mountain biking are optional. You can discuss your alternatives, costs, and availability with your tour guide.
Meals included: Breakfast


Santorini - Hiking and cruise

Today we’ll hike from Fira to Oia, all the way along the Caldera cliff edge. It is a picturesque path with no specific challenges that offers breathtaking views of the caldera. After passing via Firostefani, Imerovigli, and Skaros, we will arrive at Oia, a charming village, in about 3 hours. When you arrive at the scenic town of Oia, you will have free time to roam through its gorgeous streets, explore the modest exquisite stores, or relax and enjoy your lunch in one of the several cafes/restaurants with rooftop terraces giving excellent caldera views.

Later, we’ll descend the steps to Ammoudi Bay, where we’ll join a lovely catamaran vessel for a wonderful sailing excursion inside the caldera. You will get the opportunity to swim in the Hot Springs, see more of Santorini’s beauty, and enjoy a BBQ meal served by the staff on board. 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
Meals included: Breakfast and BBQ Dinner
Accommodation: Santorini



Today will be a fantastic day in Santorini, exploring the natural and historical grandeur of the island! In the morning, we will first visit Pyrgos, a traditional village that was designated as a «protected town» in 1955. We will next proceed to the monastery of Prophet Elias, which is located on Santorini’s highest point and offers 360-degree views of the island! From there, a spectacular, slightly steep, descending track leads us to the Ancient Thera archaeological site. From there, we’ll take the descending hiking trail to Perissa. You will have free time to relax, enjoy swimming, water sports, scuba diving, or take a walk along the long black sandy beaches of Perissa and Perivolos, followed by lunch at one of the coastal restaurants.

Following that, we will go south to the archaeological site of Akrotiri, popularly known as the «Greek Pompeii,» which is one of the most significant prehistoric settlements in the Aegean*.

Optional Activity: Instead of visiting Perivolos beach, we can organise a fantastic sea kayak adventure for those of you who enjoy sea kayaking. Starting from Akrotiri, you will paddle via the Red and White beaches, experiencing the island’s south coast in an unusual way! 
Meals included: Breakfast
Accommodation: Santorini


Santorini – Athens

Today is the final day of our seven-day trip to the Cyclades islands. You have the morning free to explore Fira and buy any souvenirs you choose before we board the boat back to Athens.

Meals included: Breakfast

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