Cyclades Dream: Sifnos, Milos and Kimolos at their finest

This is a premium trip. You stay in handpicked 3 and 4-star boutique hotels, in double rooms with private bathroom. On Sifnos, you remain four nights in the same place, facing the beach of Kamares — no need to repack each day. On Milos, two nights in an upgraded hotel in Adamas. In Piraeus, a comfortable 4-star hotel bookends your journey. Your luggage is transferred between islands; you carry only a small daypack. Single room available on request.

Breakfast each morning at the hotel. Picnics of local produce during walks. Each evening, you dine at a taverna with the group — an opportunity to taste each island's specialities: the flavours of Sifnos, reputed as the finest table in the Cyclades, the fresh fish of Milos, the cheeses of Kimolos. Meals included from dinner on Day 1 to breakfast on Day 10.

This trip is designed to be accessible and enjoyable. Walks last from 2 h 30 to 5 h per day, on well-marked trails — the famous flagstone kalderimi of the Cyclades. The pace is one of discovery: your guide adapts to the group, scheduling panoramic pauses and swimming breaks. No day is a forced march.

From 5 to 14 people, accompanied by a qualified English-speaking guide.

10 days / 9 nights / 7 days of walking.

The trip begins on Day 1 at Athens airport (orientation meeting at 6 pm in Piraeus) and ends on Day 10 at Athens airport after breakfast.

Late spring (May–June) and early autumn (September–October) offer ideal conditions: magnificent light, mild temperatures, islands free from the summer crowds. The famous Meltem breeze pleasantly refreshes the atmosphere in warmer months.

Looking to continue your discovery of Greece? Explore our trips to the Cyclades, our holidays in Crete or our escapes to the Ionian Islands. Discover Greece by bike or on a self-guided holiday at your own pace.