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Fast sailing holiday in the Cyclades: IOS-MILOS & gourmet cuisine

Next Departure:

July 26, 2025

Greece:

Cyclades

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

July - August

Suitable for travellers:

18 - 70 years

Boarding from:

Íos

What's included

Cancellation policy

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Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

French

English

Italian

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4 travellers have chosen this experience

This experience, in a nutshell

An unforgettable adventure through the fascinating Western Cyclades, starting from the sparkling island of Ios to the beautiful Milos. This sailing holiday is designed for those who wish to combine the thrill of sailing with the pleasure of discovering hidden corners of paradise.


Your journey begins in Ios. Exciting sails await you across the Aegean Sea, where the wind will be your faithful companion, giving you moments of pure fun and freedom.


We will stop at some of the most evocative islands of the Cyclades:

  • Sikinos: An unspoiled and little-frequented gem, perfect for those seeking authenticity and tranquility. With its rural landscape and vineyards, Sikinos invites you to explore the traditional village of Chora and relax in its secluded bays.
  • We will stop in Folegandros , known for its breathtaking views, and Chora, perched on a cliff overlooking the sea. Its narrow streets, whitewashed houses and spectacular views make it one of the most striking islands in the Cyclades.
  • Uninhabited and wild is Polyaigos, it is one of the best places to feel immersed in unspoiled nature, far from any sign of civilization and perfect for snorkeling.
  • Small and charming, the island of Kimolos offers a peaceful and traditional atmosphere. Its idyllic beaches and the picturesque village of Chorio, with its white houses and cobbled alleys, will make you experience the authenticity of the Cyclades.


The final destination is Milos which will fascinate you with its spectacular rock formations, sea caves and turquoise waters. Among the most spectacular are those of Kleftico, an iconic cove, once a refuge for pirates, today Kleftiko is a paradise for those who love to swim and explore the coast with mask and snorkel, among rock arches, caves and crystal clear waters. In Milos, you will discover other corners of incomparable beauty, with volcanic beaches and lunar landscapes, but also with its lively and picturesque fishing villages.



On board our boat, designed to offer comfort and performance, you will enjoy a safe and pleasant sailing experience. Your skippers, expert connoisseurs of the sea, will be happy to guide you on this adventure, sharing secrets and stories of the islands we will visit.


In addition to adventure and exploration, there will also be room for relaxation and the pleasure of good food, with lunches carefully prepared on board by your skippers.



This sailing holiday in the Western Cyclades is much more than just a trip; It is an experience that frees the mind and soul, combining adventure, nature, culture and relaxation in perfect harmony. Get ready to create unforgettable memories, immersed in the wild beauty of the Cyclades.

€1,025

6 days - 7 nights

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8+

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Boat & Classes of Service

43 - 2010

Type

Sailboat

Length

13 m.

Toilets

2

Cabins

3

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11+

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Our itinerary

Our trip starts here:

Íos.

Check-in: 6:00 PM

Our trip ends here:

Milos.

Check-out: 9:00 AM

Leg 1

We set sail from Ios

In the late afternoon, board from the port of Ios, where the adventure begins. After arranging our luggage in the cabin, we all meet together for an aperitif prepared by the skippers: a convivial moment to break the ice and get to know the group. In front of a sunset that tinges the sea with warm colors, the skippers will serve a tasty seafood dinner, with fresh and freshly prepared dishes, which will be the icing on the cake of this first evening.

Happy start to your holiday!

Leg 2

Hidden bay of Sikinos

The next morning, you leave Ios behind to reach Sikinos, a lesser-known island with unspoiled charm. After a short navigation, you will land in a secluded bay, where the clear sea invites you to dive in and explore the seabed with mask and fins. The bay reveals its tranquility and charm, offering a perfect break surrounded by nature where we will probably be the only visitors.

In the late afternoon we get back on board to head towards the tiny port of the island. From here you reach the chora of Sikinos, the ancient village clinging to the hill. After a walk through the white streets, you reach the monastery that dominates from above, perfect for admiring a unique sunset. The day ends with a dinner in the alleys of the chora, savoring traditional Greek cuisine and soaking up the authentic and timeless atmosphere of Sikinos.

Leg 3

Sails in the Wind for Folegandros

We sail with the wind crosswind, enjoying the agile performance of our sailboat, which cuts through the waves lightly and quickly.

We land in a quiet bay between islets near Folegandros, where we anchor sheltered from the waves, perfect for lunch. After lunch, we resume sailing for the few miles that separate us from the bay of the port of Folegandros,

Towards the end of the afternoon, we are about to reach the Chora of Folegandros and the ascent to the Church of the Panagia, the most iconic place in Folegandros. The climb is rewarded by a view that leaves you breathless: the fiery red sun slowly settles on the horizon, plunging into the sea with an explosion of colors.

The evening continues in the village of Kastro, a picturesque village steeped in history and authenticity. We sit in a local tavern, where we savor traditional Greek cuisine. The day ends by returning to the boat, under a clear and starry sky.

Leg 4

Sail south of Milos

The sails are hoisted in the direction of Milos.

We drop anchor in a bay surrounded by rocky walls with colored veins that change shade as the sun goes down.

This corner of paradise, light years away from the chaos and frenzy of everyday life, invites us to slow down, to breathe deeply and to immerse ourselves in an afternoon of total relaxation, where time seems to lose its incessant ticking.

The luxury of simplicity awaits us: swimming in crystal clear waters, exploring the seabed, quiet moments under the warm sun or cool shade, in a place where peace reigns supreme. With the arrival of evening, the bay is transformed into a natural theater for an unparalleled astral show, with constellations dancing in the night veil, in a silence that speaks to the heart.

Spending the night in this bay turns out to be an experience that frees the mind and soul, moments of pure relaxation and deep connection with the truest essence of nature.

Leg 5

Kleftiko: natural wonders

A traverse navigation takes us to Kleftiko, a hidden and spectacular corner of the world that can only be reached by boat. Kleftico is a real treasure, nestled between rock formations and imposing stacks that rise from the turquoise waters.

After admiring the extraordinary sand waterfalls, a natural phenomenon where the sand slides towards the sea creating a surreal landscape, we resume our navigation westwards, until we reach the enchanting Firiplaka in Milos. This corner of paradise welcomes us with its turquoise waters and golden beaches and brightly colored rock walls.

At nightfall, your skippers turn into chefs to prepare a memorable dinner: the famous tagliatelle with meat sauce. Using only eggs and flour, they create a dish from scratch that tastes of Italian tradition. This dinner on a boat, under a starry sky that only the Cyclades can offer, becomes the highlight of an already extraordinary day.

Leg 6

Polyaigos e Kimolos

After breakfast, an intense and fun sail awaits us to Polyaigos, an uninhabited island that reveals itself as a secret hidden in the heart of the Cyclades. The island, with its wild and unspoiled charm, welcomes us in an atmosphere of absolute peace.

The afternoon is all about relaxation: we enjoy refreshing baths and swims in the crystal clear waters.

In the late afternoon we resume navigation, going up the wind towards Kimolos, where a picturesque fishing village awaits us. We anchor a little offshore, admiring the view of the white houses and the colored shutters that seem to come out of a postcard.

Dinner is served on board, prepared with passion by your skippers, who give you one last convivial moment in this enchanting setting.

When the sun goes down on the horizon, we go ashore to end the evening by immersing ourselves in the authentic atmosphere of Kimolos.

Leg 7

Polyaigos

After breakfast, a short sail will take us back to Polyaigos, where we drop anchor in an extraordinary bay, a real natural pool surrounded by white sand and lapped by waters of dazzling transparency.

In the afternoon, we'll head to Adamas. If the wind is favorable, we will stop at Sarakiniko, a natural spectacle of white rocks sculpted by the wind and the sea, creating a unique lunar landscape.

Arriving in Adamas in the evening, we'll find a picturesque and lively port, the main maritime center of Milos. Here we prepare for a special evening, climbing up to the castle and monastery to watch the sunset from an exceptional vantage point.

The day ends with a visit to Plaka, the historic capital of Milos, located on a hill. Plaka is a charming and authentic village, with narrow cobbled streets, white houses and flower-filled balconies.

Leg 8

Getting there in Milos

After a last shared breakfast on board, it's time to say goodbye. You can enjoy the last moments of quiet, exchanging memories and smiles with your fellow travellers, as the sun rises high above the Aegean. With a mixture of nostalgia and gratitude, you step off the boat that was home and refuge on this unforgettable adventure, taking with you memories of crystal clear waters, breathtaking sunsets and laughter under a starry sky. A goodbye to the sea, with the promise of returning soon to sail these magical waters.

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Lorenzo & Annalisa

Member since 2013 -

Organisation

French

English

Italian

4.9/5

out of

40

reviews

Skipper

Boat

Destination

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Small Cyclades

09/14/2024

Stefan E.

-

Switzerland

Annalisa and Lorenzo are wonderful hosts and very skillful skippers. We had an amazing time with delicious food, visiting beautiful spots, swimming at peaceful hidden islands. The whole planning is flawless, given us a very relaxing trip and memorable first sailing experience. Grazie mille =D
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Small Cyclades

08/26/2024

EMANUELE P.

-

Italy

Tutto perfetto! Annalisa e Lorenzo sono bravissimi ed offrono un servizio unico. Assolutamente da provare!
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Small Cyclades

08/17/2024

Márcio R.

-

Italy

Lorenzo and Annalisa are fantastic, very experienced and know the conditions of the region well. From the first moment I felt at ease, each meal was very tasty and prepared with great care. It was my first trip of many to come!
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A week exploring the Dodecanese

07/9/2024

Matteo C.

-

Switzerland

Trattamento da crociera, no stress, non devi pensare a niente, non devi decidere niente

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