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Adventure offered by Annalisa

7 days
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This itinerary unfolds along the western and central coast of the Cyclades, following a natural progression between neighboring islands, short distances, and stops chosen for the beauty of the sea and bays. It begins in Milos, with a first day entirely dedicated to its most spectacular coastline, and continues through islands diverse in character but united by a common thread: breathtaking landscapes, clear water, and simple docking.

The route alternates short cruises with a more challenging crossing to Syros, always keeping the sea at the center of the experience. Kimolos, Sifnos, and Serifos offer sheltered bays, seaside villages, and scenic Chora, while Rineia represents a simple and quiet conclusion, facing Mykonos but far from it all.

It's a week built around nights at anchor, sea time, and sailing, with the boat as a constant point of reference.

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.
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  • Plan
    Day 1 Milos→Kleftiko 14 minutes
    Boarding begins at 11:00 a.m. and departs from the port of Adamantas around 12:00 p.m., sailing along the coast of Milos to Kleftiko, one of Greece's most iconic sites. Sea caves, natural arches, and emerald waters set the stage for the first day. Swimming, snorkeling, and total relaxation. Spend the night at anchor, beneath the moonlit white cliffs.

    Day 2 Kleftiko→Kimolos 17 minutes
    Set sail for Kimolos, a 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.

    Day 3 Kimolos→Sifnos 12 minutes
    A short sail to Sifnos. We'll stop for swimming in iconic bays like Apokofto or Faros, at the foot of the Chrisopigi Monastery: clear sea, unspoiled scenery, and a timeless atmosphere. Depending on the weather, we'll spend the night at anchor in Vathy, a small seaside fishing village, or Kamares, the main port, where we'll dine in a traditional taverna.

    Day 4 Sifnos→Serifos 16 minutes
    We continue towards Serifos, a rugged yet luminous island. We'll anchor near Livadi or in a nearby bay like Psili Ammos. Those who wish can climb up to Chora to admire one of the most beautiful sunset views in the Cyclades. Spend the night at anchor.

    Day 5 Serifos→Syros 25 minutes
    The longest crossing on the Syros itinerary. A day spent at sea on the west coast, in quiet bays like Finikas or Galissas, offering beautiful sunset views. A night at anchor.

    Day 6 Syros→Rineia 22 minutes
    Our last long sail to Rineia, an uninhabited island opposite Mykonos. Here, time stands still: crystal-clear water, absolute silence, and no buildings. Long swims, dinner on board, and a starry sky for our last night at anchor.

    Day 7 Rineia→Mykonos 10 minutes
    Our journey concludes: six islands, six nights mostly at anchor, and the boat as our only anchor in the sea. A short sail will take us to Tourlos Marina in Mykonos for disembarkation around 12:00 PM. A self-guided visit to the sacred island of Delos is highly recommended.
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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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Itinerary
Annalisa
Meet Annalisa, the skipper
At Sailwiz since 2026
We are Annalisa and Emanuel, expert skippers and life and travel companions. We love combining the pleasure of sailing with the exploration of places, history, and local customs, capturing their most authentic essence. Our philosophy? Wind in the sails, secluded anchorages, and cuisine prepared with care and imagination.
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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.
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Specifications
  • Model: Dufour Yachts - 455 GL
  • Capacity: 6 spots
  • Length: 13.75 m
  • Cabins: 4
  • Year: 2006
  • Bathrooms: 3
Features
  • GPS
  • Life jackets
  • VHF
  • Sounding line
  • Electric windlass
  • Autopilot
  • Wind equipment
  • EPIRB
  • Tender
  • Shower
  • Bimini
  • Fishing rods
  • HI-FI equipment
  • Wifi
  • Equipo de snorkel

Additional Information

Included
  • Final cleaning
  • Professional skipper
  • Bed linens
  • Paddle Surf
  • Tender
  • Fishing equipment
  • Tourism taxes
  • Fishing bait
  • Equipo de snorkel
  • Towels
  • Waiter/Cook
Not included
  • Costs of mooring and anchoring
  • Meals on board
  • Food and drink on land
  • Gas
  • Moorings
  • Snacks
  • Skipper's food
Payment methods
  • Credit/debit card
  • Wire transfer
User questions and answers
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Next dates

  • 4 Aug · 7 days
    Confirmed, places available Confirmed, Full
    1150 € /person
    6325 € /boat
    Book now
  • 8 Sep · 7 days
    Confirmed, Full Confirmed, Full
    1000 € /person
    5500 € /boat
    Book now
    Book now
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