From Santorini to Milos: Sailing the Most Beautiful Cyclades with …

This trip is designed for those who want to immediately enter the heart of the Aegean, starting from an iconic location. The first night in Thirasia, at the buoy, allows you to experience Santorini from a rare perspective, with the sunset light over Oia and the silence.

From here, the route winds west and north, following balanced stops and distances designed to leave room for the sea, stops at anchor, and life on board. Southern Ios, Sikinos, and Folegandros offer sheltered bays, small ports, and secluded Chora with a unique charm.

The central part of the journey touches Polyaigos and Kimolos, among the least inhabited islands of the Cyclades: clear anchorages, clear seabeds, and days dedicated to the sea, without the need to travel. The final sail skirts Milos, choosing the best side based on the conditions, until disembarking in Adamantas.

It's a week that favors continuity, open spaces, and discreet landings, with a natural progression from the volcanic landscape of Santorini to the white, rugged coasts of Milos.

There are several boarding options available:
• Cabin charter: shared double cabin
Booking a bed in a double cabin, shared with another guest of the same gender.
• Double cabin for single use
Book your cabin for exclusive use, with a 40% discount on the second rate.
• Exclusive boat
Charter the entire vessel for a private group of up to six guests, with more advantageous conditions than individual reservations.

We take care of the galley (paid for by the common fund) and the onboard cuisine, paying particular attention to the quality of the ingredients and the pleasure of sharing. Life on board is informal, but with a few rules: after meals, settling in naturally becomes a time for collaboration.

We use porcelain tableware and crystal glassware, a conscious choice to reduce plastic use and enhance even the simplest gestures. For washing, we use seawater wherever possible, followed by a final rinse in fresh water.

Days begin with a Mediterranean breakfast, featuring Greek yogurt, honey, fresh and dried fruit, bread, butter, jams, cheeses, and cured meats. Lunches are light and fresh, inspired by Greek, Italian, and seasonal cuisine, while dinners are a time to savor slowly: raw seafood, grilled fish and meat, fresh vegetable creations, and dishes prepared with local ingredients.

While meals on board are one of the most special moments—eating on board, with the sea all around and the silence of the harbor—we always plan a couple of opportunities to enjoy authentic Greek cuisine in traditional taverns.

Meal times also follow the rhythm of the sea, adapting to routes and weather conditions.

Plan

Day 1 Santorini → Thiresia 10 nm
Board the tender at around 11:00 a.m. at Red Beach, Akrotiri. Sail beneath the caldera, bathe in the hot springs, and enjoy unique views of the volcanic cliffs. A sunset cruise and a night at a buoy on the islet of Thiresia with a view of Oia.
Day 2 Thiresia → Ios south 20 nm
We'll depart early in the morning, sailing close-hauled to the south of Ios, where the water is crystal clear, with beaches and seabeds ideal for swimming and relaxing. We'll spend the night at anchor in Manganari Bay.
Day 3 Ios → Sikinos 15 nm
Departure for Sikinos, one of the most secluded islands in the Cyclades, perfect for a quiet and authentic stop. Before arriving at our destination for the night, we'll stop in a bay for a swim in the clear waters, away from the crowds. The landing at Alopronoia is simple: a small port overlooking a beach, with a few seaside tavernas where you can enjoy a casual dinner.
Day 4 Sikinos → Folegandros 15 nm
First stop in Folegandros is the spectacular Katergo Bay, nestled between towering cliffs, before arriving at Agkali Beach. Buses depart from the beach for the beautiful Chora, which can also be reached on foot. Dinner at a traditional taverna.
Day 5 Folegandros → Polyaigos 18 nm
We're heading for Polyaigos, dotted with small bays, including Mersini and Black Galatia. Here we'll spend a lazy day at sea and a night at anchor.
Day 6 Polyaigos → Kimolos 5 nm
Set sail for nearby Kimolos, another small, secluded and authentic island. Anchor in one of its most beautiful bays, such as Prassa or Bonatsa, with pale sand and turquoise sea. Enjoy an afternoon at the beach and a quiet evening at anchor in Agios Barbara Bay.
Day 7 Kimolos → Adamantas 14 nm
Coastal navigation of Milos to the port of Adamantas for disembarkation around 12:00, depending on weather conditions: north if the Meltemi wind allows, with a view of the spectacular Sarakiniko, or south, with a stop at the iconic Kleftiko.

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Other information

The skipper for this activity speaks english, french, german, italian and spanish. To participate you must speak one of the languages spoken on board.

Expenses not included are covered by the common fund, which is approximately €200-250 per person, added to the boarding fee. Anything not specifically listed under "Included" and "Not Included" is not provided. For example, insurance, airport transfers, etc. When in doubt, always ask.

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Boat details

The boat has a commercial license and has the necessary permits and safety equipment to operate professionally in Greece. It is rigged as a cutter with a double jib to safely handle all the Aegean winds. It has four double cabins with double beds and three bathrooms. At each crew change, the cabins are sanitized and furnished with made beds, bath linens, and beach towels included. All cabins have windows and fans. The bimini top remains open at all times, even when sailing, to protect you from the Greek sun. The cockpit features comfortable cushioned seating and a large table with extendable wings, perfect for dining with a sea view. At the stern, there is a barbecue, the star of evenings on board. All tableware is porcelain and glassware is crystal, to reduce plastic consumption. We practice recycling. We use seawater wherever possible for washing, followed by a final rinse in fresh water.

Specifications