15-day island hopping in Greece – Mykonos, Naxos, Sifnos, Paros & Santorini

Day 1: Departure for Mykonos

The journey begins with a flight to Mykonos. The island has a distinctly dual character: during the day, beaches offer a sense of freedom and calm; in the evening, Mykonos transforms into a lively setting of music and lights.

Whitewashed houses contrast with the deep blue sea, while narrow streets connect the harbour to the iconic windmills. Tradition and modern life blend effortlessly here.

Day 2: Mykonos Town and Harbour

The walk starts at the iconic windmills overlooking the sea. Winding paths lead between white houses with blue shutters and bougainvillea into the heart of the town, where narrow streets unfold like a maze. Small boutiques, galleries and cafés line the way.

The walk ends at the harbour, where fishing boats gently bob on the water and terraces look out over the sea. One of the harbour restaurants serves the fresh catch of the day.

Day 3: The Beaches of Mykonos

In the 1960s, Jackie Onassis gave Mykonos an international allure. With her large sunglasses and effortless style, she became a familiar presence on the island long before it turned into a fashionable destination. Mykonos combines freedom, luxury and a festive atmosphere by the water. Here, the line between day and night fades, and summer seems endless.

Day 4: Ferry to Naxos

The ferry takes you to Naxos, the largest and most fertile island of the Cyclades. The interior reveals a patchwork of vineyards, orchards, traditional villages and historic sites. A drive through the Traga Valley passes Belonia and Apiranthos, the fishing village of Apollonas, and the monasteries of Faneromenis and Ypsilatera. You stay three nights on Naxos.

Day 5: Naxos Town and the Portara

Naxos is known for its sandy beaches and Venetian heritage. The Portara gate dominates the harbour of Naxos Town. The Kastro forms one of the best-preserved Venetian citadels in the Cyclades. The day is free to explore the harbour, citadel and nearby beaches.

Day 6: Ferry to Sifnos

On Sifnos, time seems to slow down. The island has no airport and remains relatively unspoilt. White villages sit naturally in the landscape, interspersed with terraces, olive trees and countless small chapels watching over sea and land.

Day 7: Chrisopigi Monastery and the Seven Martyrs

The Panagia Chrisopigi Monastery stands on a rocky outcrop in the sea and is the symbol of the island. A second viewpoint is offered by the Church of the Seven Martyrs, reached by a staircase connecting the church to the mainland. The view over the Aegean Sea is part of the experience.

Day 8: Sifnos, Slow Down

Midway through the journey, a day without a programme. Time for the pool, the terrace and silence, before boarding the next ferry.

Day 9: Ferry to Paros

Paros lies at the heart of the Cyclades and is, after Naxos, the largest island of the archipelago. The capital, Parikia, has an old town with Byzantine and Venetian influences. Naoussa features one of the most beautiful fishing harbours in the Cyclades. Ancient marble quarries and the butterfly valley can also be visited. You stay three nights in a Caractère hotel.

Days 10 and 11: Paros and Antiparos

A kaïk from Parikia or Pounta takes you to Antiparos. This small island has just one village: Kastro. Its mountainous landscape and natural beauty contrast with the more cosmopolitan atmosphere of Paros. The cave of Agios Ioannis extends more than one hundred metres into the mountain and reveals stalactites formed over thousands of years.

Day 12: Ferry to Santorini

Santorini’s main attraction is the caldera: a steep volcanic wall against which white villages cling like birds’ nests. Steep slopes create spectacular views. The setting feels almost cinematic, with sun-drenched terraces, an endless blue sea and a carefree island atmosphere made famous worldwide by an iconic musical love story. Each evening, the sunset paints the sky in shades of red and gold above the submerged volcanic crater.

Day 13: Fira and Donkey Paths

Fira is the capital of Santorini. You wander through narrow streets, visit the Orthodox cathedral and may encounter groups of donkeys. They were traditionally used to transport goods from the harbour up to the town above, their arrival announced by the sound of colourful bells.

Day 14: Oia and Imerovigli

You begin high on the cliffs of Imerovigli, where the caldera stretches out like an ocean of blue. The Skaros Rock stands as a silent guardian. Each step along narrow paths brings you closer to the horizon.

You then slowly descend towards Oia, where the white of the houses contrasts sharply with sea and sky. Narrow streets wind between boutiques and terraces, while the sun reflects off blue-painted domes. At sunset, the village seems to glow as gold, pink and orange merge and the rhythm of the island gently pulses.

Day 15: Departure or Extension

It is time to return home. A possible extension to Serifos adds five days to the journey. The island is known for its sandy beaches and the harbour town of Livadi, with mining architecture dating back to the 19th century. Caractère arranges the extension on Santorini or the crossing to Serifos.

What budget should you expect? For this journey, expect an indicative price from €15,000 for 2 people. This price includes international flights, ferry crossings, and accommodation in a room with breakfast and depends on your travel dates, hotel selection, and any extras such as excursions or extensions.