Two weeks island hopping in the Greek Cyclades

Greece itinerary


1

Created by:
itinerary-hub

Published on:
Oct. 15, 2020

14 days

688 km

7 steps


This is a two week itinerary in the Greek island group of the Cyclades in the Aegean Sea. Visit some of Greece's most beautiful and picturesque islands with stunning landscapes and authentic towns.

Step 1: Naxos

2 days recommended

Naxos
Category Rating
atmosphere
scenery
tourism
food
beach
culture
nightlife
wildlife
adventure

Naxos

Naxos is the largest island in the Cyclades, offering a perfect mix of beautiful beaches, historic sites, and traditional villages without the tourist crowds of its neighbors. The island's main town, also called Naxos or Chora, welcomes visitors with its iconic ancient marble doorway - the Portara - standing tall since 522 BC, framing gorgeous sunset views.

The island has an impressive history dating back thousands of years. Once an important center for Cycladic civilization, Naxos later became known for its marble quarries, which provided materials for many ancient Greek sculptures and buildings. Today, you can still see impressive marble statues called 'kouros' left unfinished and abandoned in ancient quarries.

Naxian cuisine is worth noting - the island is famous for its exceptional local produce. The fertile land yields fantastic potatoes, cheese (especially the local graviera), and citrus fruits. Naxos also produces its own distinctive spirits, including kitron, a liqueur made from citron leaves.

The mountainous interior hides charming villages like Apeiranthos, known for its marble streets and preserved architecture. These inland communities maintain authentic Greek traditions and offer a glimpse into local life that coastal resorts often lack. With crystal clear waters along its shores and rugged mountains dominating its interior, Naxos provides a more diverse landscape than most Greek islands.



step 1: Naxos

Transportation type:

car/bus/boat

54 km / 33 miles

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step 2: Ios


Step 2: Ios

2 days recommended

Ios
Category Rating
atmosphere
scenery
tourism
food
beach
culture
nightlife

Ios

Ios is a small but vibrant island in the Cyclades group in Greece, famous for its beautiful beaches and lively nightlife. The main town, Chora, sits on a hilltop with its characteristic white-washed buildings and blue-domed churches creating that classic Greek island look that you always see in photos.

During summer, Ios transforms into a party hotspot, attracting younger travelers looking for fun. However, there's much more to this island than just partying. The island has over 30 beaches, with Mylopotas being one of the most popular thanks to its golden sand and clear blue waters.

Ios also has an interesting history dating back thousands of years. It's said to be the final resting place of the famous poet Homer. The island was named after the ancient Greek word for violets, which supposedly once covered its hills.

Beyond the beaches and bars, Ios offers authentic Greek culture in its more remote villages. Local tavernas serve traditional Greek cuisine using fresh ingredients from the island.

The island strikes a nice balance between developed tourist areas and untouched natural beauty. It's possible to find secluded spots even during the busy season if you're willing to explore beyond the main areas.



step 2: Ios

Transportation type:

car/bus/boat

50 km / 31 miles

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step 3: Santorini


Step 3: Santorini

2 days recommended

Santorini
Category Rating
atmosphere
scenery
food
beach
tourism
culture
wildlife
adventure

Santorini

Santorini is nothing short of spectacular. This Greek island in the Aegean Sea stands out with its iconic white-washed buildings topped with bright blue domes perched on dramatic cliffs. The island is actually what remains of a massive volcanic eruption that occurred around 3,600 years ago, which created the stunning caldera views that leave visitors in awe.

The sunsets in Oia are famous worldwide, painting the sky in vibrant oranges and pinks as the sun dips below the horizon. But Santorini offers more than just pretty views. The island boasts unique black, red, and white sand beaches due to its volcanic nature. The ancient site of Akrotiri provides a fascinating glimpse into Minoan civilization preserved under volcanic ash, sometimes called the 'Greek Pompeii.'

Food lovers will appreciate Santorini's culinary scene, featuring local specialties made with ingredients grown in the volcanic soil. The island produces exceptional wine from grapes cultivated in some of the oldest vineyards in the world, where vines are trained into unique basket shapes to protect them from strong winds.

While summer brings crowds, Santorini holds its charm year-round. The island balances its tourism fame with authentic Greek culture that persists in villages away from the main tourist spots, where locals continue traditions that have existed for generations.



step 3: Santorini

Transportation type:

car/bus/boat

142 km / 88 miles

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step 4: Milos


Step 4: Milos

2 days recommended

Milos
Category Rating
atmosphere
scenery
tourism
food
beach
culture
nightlife
wildlife
adventure

Milos

Milos is a volcanic island in the Aegean Sea, part of the Cyclades group in Greece. It's famous for its incredible moon-like landscapes and more than 70 beaches with crystal clear waters in all kinds of colors - white, pink, and red sands surrounded by turquoise waters.

The island is where the famous Venus de Milo statue was discovered in 1820, which now sits in the Louvre Museum in Paris. This gives you an idea of the rich history that runs through Milos - with ancient catacombs dating back to the 1st century and remnants of mining operations that have been active since prehistoric times.

The main town, Plaka, sits on a hill with narrow streets perfect for exploring. Nearby, Klima is a traditional fishing village with colorful boat houses (syrmata) built into the rocks right at the water's edge. These unique structures serve as homes on the top floor and boat storage below.

The local cuisine focuses on fresh seafood and traditional Greek dishes, often with a twist unique to the island. And unlike some of its more famous neighbors like Santorini or Mykonos, Milos offers an authentic Greek experience without massive crowds, making it a perfect spot for travelers looking to experience the beauty of the Cyclades in a more relaxed atmosphere.



step 4: Milos

Transportation type:

boat

294 km / 182 miles

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step 5: Serifos


Step 5: Serifos

2 days recommended

Serifos
Category Rating
atmosphere
scenery
tourism
food
beach
culture
hiking
wildlife

Serifos

Serifos is a stunning Cycladic island in Greece that sits a bit off the radar compared to its famous neighbors like Santorini or Mykonos. That's exactly what makes it special - fewer crowds but all the Greek island beauty you could want.

The island is known for its pristine beaches with crystal clear waters. Livadakia, Agios Sostis, and Psili Ammos are some of the most beautiful spots to enjoy the Mediterranean sun. The main town, Chora, perched on a hill overlooking the harbor, looks like a perfect postcard with its white houses climbing up the rocky slope.

Serifos has a rich mining history dating back to ancient times. The abandoned mines near Megalo Livadi tell stories of the island's industrial past, which peaked in the early 20th century before declining. These rusty remnants create an interesting contrast against the natural beauty of the landscape.

The local cuisine focuses on fresh seafood and traditional Greek dishes, often with a unique Serifos twist. Marathopites (fennel pies) are a local specialty worth trying, along with the island's goat cheese and thyme honey.

With only about 1,400 permanent residents, Serifos maintains an authentic Greek island atmosphere that's increasingly hard to find. The locals are known for their hospitality and maintaining traditions that have nearly disappeared on more developed islands.



step 5: Serifos

Transportation type:

car/bus/boat

76 km / 47 miles

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step 6: Paros


Step 6: Paros

2 days recommended

Paros
Category Rating
atmosphere
scenery
tourism
food
beach
culture
nightlife
wildlife
adventure

Paros

Paros, a stunning island in the Cyclades, is often celebrated for its enchanting combination of traditional Greek charm and beautiful beaches. It's a place where whitewashed villages with blue-domed churches sit beautifully against the backdrop of the Aegean Sea.

This Greek paradise offers a perfect balance of relaxation and adventure. The island is famous for its fine white marble, known as Parian marble, which was used to create masterpieces like the Venus de Milo. The main town of Parikia and the fishing village of Naoussa are filled with narrow cobblestone streets, blooming bougainvillea, and tavernas serving fresh seafood.

Paros has a rich historical past, with traces of Minoan, Mycenaean, and Byzantine civilizations. The Church of Ekatontapiliani (Church of 100 Doors) in Parikia dates back to the 4th century and is one of the oldest and most important Byzantine monuments in Greece. Beyond history, the island is also a water sports hub, particularly for windsurfing at Golden Beach.

The local food scene is vibrant with restaurants serving traditional Greek dishes using locally sourced ingredients. Paros offers a delightful mix of cosmopolitan vibes and authentic Greek island life, making it an appealing destination for all types of travelers.



step 6: Paros

Transportation type:

car/bus/boat

70 km / 43 miles

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step 7: Mykonos


Step 7: Mykonos

2 days recommended

Mykonos
Category Rating
atmosphere
scenery
food
beach
tourism
culture
nightlife
wildlife

Mykonos

Mykonos is a stunning island in Greece's Cyclades group, known for its bright white buildings with blue doors that look amazing against the backdrop of the clear blue Aegean Sea. This island has a perfect mix of relaxing beaches and exciting nightlife that keeps tourists coming back year after year.

The island has a rich history dating back to ancient Greek mythology, supposedly named after the grandson of Apollo. In the 1960s, it became popular among celebrities and the international jet set, helping transform it from a simple fishing village to a world-class destination. Today, the island keeps its traditional Cycladic architecture while offering modern luxury experiences.

Mykonos Town (Chora) is the heart of the island with its famous Little Venice area and the iconic windmills that have become the island's trademark. The maze-like streets were originally designed to confuse pirates but now create a charming atmosphere for exploring the many boutiques, restaurants, and galleries.

Beyond the beautiful beaches and party scene, Mykonos has archaeological sites worth visiting, including the nearby island of Delos, the mythical birthplace of Apollo. The local food scene offers incredible Greek dishes, fresh seafood, and excellent local wines that complete the Mykonos experience.


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