Imagine waking to the scent of jasmine in a boutique hotel on Sifnos, stepping onto your terrace to find the Aegean sparkling below. Your English-speaking guide greets you at breakfast with the day's plan: a walk along ancient flagstone paths to a hilltop monastery, a swim in a hidden cove, lunch at a taverna the guidebooks haven't found. This is the Cyclades as they were meant to be discovered — unhurried, intimate, with every detail taken care of.
This premium 10-day journey through three secret islands of the Western Cyclades has been crafted for those who appreciate the finer things. Upgraded 4-star hotels, carefully chosen for their character and location, ensure you return each evening to genuine comfort. Your guide, specifically trained for English-speaking travellers, brings these islands alive with stories of local traditions, hidden chapels and the best sunset terraces.
This trip is also available with a French-speaking guide at a different comfort level and price point.
Itinerary

Program
From Piraeus, a ferry carries you to Sifnos (approximately 2 h 30). The island appears, white and luminous, one of the most attractive in the Cyclades for walking. Settle into your hotel at Kamares, facing a pretty beach, for four nights. After a swim and a picnic with your feet in the sand, you set off for a gentle first walk. The path takes you from Kastro, the fortified former capital perched above the sea, south to the charming harbour of Faros and the monastery of Chryssopigi, built on a tongue of rock reaching into the waves. An optional longer route continues inland to Apollonia, through irrigated valleys to the monastery of Vryssi and the village of Exampela.
From Apollonia, a path punctuated with chapels climbs to the monastery of Profitis Ilias, the highest point of the island. The 360-degree panorama embraces the entire archipelago — an unforgettable moment of contemplation. The descent passes through the cave of Vougnous and the springs of Kalamitsi before reaching the bay of Vathy, where a welcome swim awaits in crystalline waters. Evening at a waterfront taverna.
Beautiful paths lead to Artemonas and its cobbled lanes bordered by bougainvillea, then to the celebrated chapel of Panaghia Poulati, suspended above the sea. You follow the coast to Kastro, where shaded alleyways invite leisurely exploration. The charm of this fortified village, between centuries-old stones and maritime panoramas, stays with you long after. Return via Kato Petali and Apollonia. Taverna dinner.
Starting from Platis Gialos, an immersive loop takes you between olive groves and volcanic rocks of surprising hues. Among the trees, you come across the pretty abandoned farm of Moussia. The sea reappears, and the colours of the volcanic formations catch the eye. From here, the tiny islet of Kitriani reveals a small chapel — the oldest on Sifnos. The walk ends on the superb beach of Platis Gialos, where time pauses for a long swim and a moment of pure serenity. Taverna dinner.
A short ferry crossing to Milos (30 to 50 min). Settle into your 4-star hotel in Adamas for two nights. In the afternoon, you discover the island's north coast: the chasm of Papafranga with its transparent waters, the tiny natural harbours of Pachena and Mytakas, and the lunar white rock formations of Sarakiniko, veritable natural sculptures. Every bend in the trail reveals a new palette of colours. Taverna dinner.
A brief crossing (20 to 30 min) to Kimolos, an overlooked volcanic gem. You climb to Chorio and its windmills aligned along the ridge, then reach the rock of Skiadi, a remarkable mushroom-shaped stone sculpted by erosion. The rest of the day takes you from beach to beach, swimming in limpid waters. Return along stony paths through a shaded valley, between hamlets and silence. Ferry back to Milos. Taverna dinner.
A day devoted to Milos's cultural treasures and colourful villages. You reach Klima, a fishing hamlet whose houses painted in blue, red, yellow and green are reflected in the calm waters. Visit to the catacombs, a unique testimony to early Christianity in Greece. Climb to Plaka, the capital, for a legendary sunset over the caldera. Farewell taverna dinner.
Transfer to Athens airport after breakfast. You leave with the scent of wild thyme, the taste of Sifnos wine, and the light of the Cyclades in your memory.
Dates, prices and booking
Price does not include
- flights to/from Athens
- drinks
- entrance fees to sites not mentioned in the itinerary
- personal expenses
- insurance (required for participation)
- booking fees
- anything not listed under "Price includes"
- accommodation for 9 nights in double occupancy rooms (3 and 4-star hotels)
- meals from dinner on Day 1 through breakfast on Day 10
- private transfers as described in the itinerary
- ferry and boat tickets
- airport transfers
- English-speaking certified guide
- site entrance fees as described in the itinerary
- accommodation and government taxes
- single room supplement: on request (varies by season)
- additional night in Athens: on request
Your advisor

Giovanna Crippa
Product Manager Europe
Practical information
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.
Reviews
5 · 6 reviews
Cathy Minois 12/27/25
— Magnificent trip. Beautiful scenery. Good balance between hiking, swimming and resting. Mathieu is an excellent guide and a very nice person. Very professional and attentive. Sifnos and Kimolos are two very unspoilt and wild islands.
Michele 12/27/25
— Beautiful scenery. A great guide
—
— Réponse de l'équipe
Graziella 12/27/25
— Satisfying
Solange 12/27/25
— Beautiful scenery, a guide who made herself available to us, a great way to discover the island of Sifnos.
—
— Réponse de l'équipe
Not quite the trip you had in mind?
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