Cyclades
Greece
Explore the Cyclades island-hopping itinerary

Explore the Cyclades island-hopping itinerary

4 Reviews | Local experience, Nature, Sightseeing

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10 days
5 destinations
From 2.150€ pp
30 awesome beaches
10 archeological sites
Endless Greek delicacies

The Cycladic islands are characterized by white-washed houses, turquoise blue seas, olive groves, and sun-parched landscapes. It is here where the man lived in harmony with the environment for thousands of years. Island hopping is the best way to connect with this past and get to know the islands, each of them stamped with its unique character.

The trip will start in Athens, and after visiting the Acropolis and the new Acropolis museum, you will hop on our ferry to Tinos. Tinos is a wonderland of natural beauty, dotted with more than forty marble-ornamented villages found in hidden bays, on terraced hillsides, and atop misty mountains. The next stop is Naxos, the biggest and one of the most beautiful islands of the Cyclades. It is an island with incredible landscape interchanges with Venetian castles & traditional villages perched on its mountains cliffs. From Naxos, you will sail for the day to the Little Cyclades, a group of tiny islands that lie between Naxos and Amorgos. The final stop will be Santorini, an island famous for its amazing landscape. A jaw-dropping scenery of cliffs, blue water, and whitewashed stone villages coupled with an amazing culinary heritage.

Days

1 2 3 4 5 6 7 8 9

Day 1 Athens

Often referred to as the cradle of Western civilization, Athens has remained a colorful and vivid city. You can’t move without bumping into an ancient ruin or building, which evokes imagery of the Greek gods or the thoughts of their
philosophers. In the afternoon, you will meet your guide at the hotel lobby for an introductory talk. You will walk around Plaka, the oldest neighborhood of Athens, where you will have our first dinner at a traditional Athenian restaurant.
Day 2 Athens-Tinos

No matter how many photographs you’ve seen, nothing can prepare you for visiting and walking around Acropolis. Alongside a private guide, you will explore the site and head towards the stunning Acropolis Museum. In the afternoon, you will drive to
the port of Rafina to embark on the ferry to Tinos island. In Tinos, the core beauty is hiding behind the extraordinarily and well-preserved villages, the stone huts, the architectural details of the unique dovecotes, and the “handmade” terraces that cover the island terrain.
Day 3 Tinos

The day will start in Falatados, and from there, you will hike around the valley of Volax until you reach the village. Cottages crouch among smooth round boulders, which tumble down the mountain like giant bowling balls. Nobody knows how
these peculiar rock formations evolved. Some say there was a volcanic eruption; others claim that meteorites rained down from the sky. The 20th-century Greek philosopher Cornelius Castoriadis simply concluded that Tinos was “not made by human hand”. From Volax you will hike to the imposing rock of Exombourgo, with its medieval castle on top of it. Before we descend towards the town, you will visit a local house where you will take a cooking lesson and learn how to make traditional Cycladic recipes.
Day 4 Tinos-Naxos

After an authentic Tinian breakfast, you will be transferred to the port to embark on a ferry to Naxos. As the ferry arcs toward the island, you will catch the first glimpse of the Portara, a marble gateway on the
headland, all that remains from an ancient temple dedicated to Apollo. After settling in at your hotel and having a light lunch, you will head towards the start of the hike, right next to the place where the two “small” Kouroi (male statues) of Naxos lay down for the last 2600 years. You will continue onwards the Upper Castle, the former Venetian stronghold, passing olive groves interspersed with elements of the phrygana and maquis, and you will end up to Chalki, one of the most beautiful villages on the island.
Day 5 Naxos-Little Cyclades

Today, we will stumble across locals’ secret spot: Small Cyclades. Tucked away between the larger Cycladic islands of Naxos and Amorgos, the Small Cyclades consist of a group of islands that form a place of sheer & tranquil beauty. Life
is slow here, a microcosm right in the middle of the Cyclades. Here, the local people have a different sense of time and mindset. Locals live mainly from fishing – it is claimed that there are more boats than residents – and there are no real roads and hardly any cars, so everyone either walks or cycles.
Day 6 Naxos

Naxos is home to the highest mountain in the Cyclades, Mount Zeus and the hike to the top of it is probably the most epic thing to do in the region. Mount Zeus has a historical significance because, in ancient
times, the local Greeks believed that the cave on the northwest flanks was the birthplace of the god Zeus. As you climb, you’ll get the distinct feeling that Greek mythology is rooted in reality. After the hike, you will go for lunch in Apiranthos, which seems to grow out of the stony flanks of the mountains. The afternoon is free, and our recommendation is to visit the gorgeous sandy beach close to your hotel. After a fulfilling hike, swimming in the Aegean crystal waters is the best way to refresh body & mind.
Day 7 Naxos-Santorini

The town of Naxos is considered one of the most beautiful towns in the Cyclades, particularly popular for its fine architecture that is composed of Venetian and Cycladic elements. In the morning, you will explore the impressive Venetian castle that
stands on top of it. Later on, during the day, we will catch the ferry to Santorini. After settling in at your hotel cited in the caldera, you will hike the picturesque trail between Imerovigli and Oia, which is one of the must-do things when visiting Santorini. With breathtaking views and stunning vistas at every turn, this trail is going to be one of the prettiest ones you’ve ever hiked.
Day 8 Santorini

In the morning, you will head towards Akrotiri, Santorini’s principal archaeological wonder, a town destroyed by the volcano eruption, but preserved under layers of lava. In the Akrotiri ruins & museum area, you will enjoy your private guide will introduce
you to the history of the area. Following this, you will put on your bathing suits, and paddle into one of the most scenic areas of the island. Kayak is a wonderful way to explore the dramatic south-coast line of Santorini, especially the Red Beach which has high red cliffs and smooth hand-sized pebbles submerged under clear water. In the afternoon, you will visit one of the best wineries on the island, and during the wine tasting paired with local delicacies, you will be introduced to many different award-winning wines.
Day 9 Santorini-Athens

In the morning, you will do an easy walk towards the main town of the island, Fira. The path follows the edge of the caldera and passes several churches and houses, and offers the opportunity to soak in amazing views.
In Fira, you will have time to visit the Prehistoric Museum, as well as to see frescoes and other artifacts from Akrotiri’s ancient city. After lunch, you will have a transfer to Santorini airport to catch your internal flight to Athens. After check-in in your rooms and refreshment, you are going to have a farewell dinner.

This is a sample itinerary and can be fully customized according to your travel plans and needs. The price of this trip is indicative, given that it can change depending on several factors, including the season, activities, etc. In every case, our savvy travel experts will create a travel plan based on your budget and your bucket list! The travel planning service is free of charge and includes as many changes and customizations as you wish, until you’re fully satisfied with the result.

What's included?

Accommodation
In-country transportation
Trip planning by our travel experts
Activities and tours
24×7 support during your trip

What's not included?

Food & Drinks
International flights

Reviews: 4

Satisfaction: 5

We absolutely ADORED this trip to the Cycladic islands!

Aug 10 2020

by traveler: Tina J.

The beauty of these islands was insane, even better than on the postcards and the internet! The highlight of the trip was the Small Cyclades islands, which are completely off the beaten trail and very peaceful. It was like a whole other world! We can't wait to be back!

This island-hopping trip was amazing!

Aug 7 2020

by traveler: Jonas N.

We had plenty of time to snorkel and swim. Kayaking was an unforgettable experience, it was the first time we tried it and can’t wait to do it again. The staff was friendly and helpful, they gave us plenty of information about the sites and got us to the best swimming spots. A must-do!

Cyclades island hopping

Jul 29 2020

by traveler: Peter T.

A great way to see the best of the Cyclades, both the popular and the less known islands. The best part was the sunset watching at the end of the day, right from the deck! It was something we’ll never forget. Also, the trip had the perfect amount of relaxation and adventure, highly recommended!

Amazing island hopping experience in the Cyclades!

Jul 1 2019

by traveler: Jane K.

The staff were so helpful and kind, they constantly made sure that everything was good and provided us with tons of useful information. Everything was taken care of down to the last detail! I highly recommend it!

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