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

This itinerary is designed for those seeking the sea in its most authentic form, without rushing or forced stops. Distances are balanced, and the sailings leave room for time on board, stops at anchor, and places truly worth exploring.
We depart from Milos, with its coastline sculpted by wind and sea, and gradually descend southward, crossing islands of undeniable charm. Arriving in the caldera of Santorini is a moment that alone makes the journey worthwhile. In the midst, and all around, the deep blue sea and the dazzling light of authentic Greece.

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 Milos → Kleftiko 10 min
Boarding around 11:00 a.m., departing from the port of Adamantas for a coastal cruise along Milos. Arrival at the white cliffs of Kleftiko, one of the most iconic sights in the Aegean: sea caves, natural arches, and emerald waters. Spend the night at anchor.
Day 2 Milos → Folegandros 25 minutes
We'll sail along the southern coast of Milos toward Folegandros. We'll arrive at Agkali Beach. Buses depart from the beach for the stunning Chora, a must-see. Dinner at a traditional taverna.
Day 3 Folegandros → Sikinos 15 minutes
Stop at the spectacular bay of Katergo, nestled between towering cliffs, before setting sail for Sikinos, a discreet and authentic island. Anchor or moor at Alopronoia, a small, quiet port, or in one of the nearby bays. Spend the night at anchor or in port.
Day 4 Sikinos → Ios 15 minutes
Sail to the east coast of Ios. We'll dock in the port or anchor in one of the nearby sandy bays, from which we'll walk to the beautiful Chora of Ios to watch the sunset from the church of Panagia Gremiotissa, which overlooks the entire Chora, the port of Mylopotas, and, on clear days, the neighboring islands. Dinner at one of the traditional tavernas.
Day 5 Ios 12 mn
We'll continue sailing south, exploring some of Ios's beautiful bays before spending the night at anchor in Manganari Bay: crystal-clear water and a seabed ideal for swimming and relaxing.
Day 6 Ios → Santorini 15 minutes
Last crossing to Santorini. The arrival by sea is spectacular: the caldera suddenly opens up with its volcanic cliffs. We moor at the buoy on the islet of Thiresia with a view of Oia and set out at sunset to admire the sun turning the sea orange.
Day 7 Santorini 10 nm
The morning is dedicated to Santorini: sailing beneath the caldera, bathing in the hot springs, and enjoying unique views of the volcanic cliffs. Arrival south of Santorini at Red Beach for disembarkation by tender around 12:00 (buses to Thira also depart from here).

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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