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Sailing trip in the Cyclades

Experience a dreamlike sailing trip through the Cyclades – characterized by white villages, turquoise waters, and the incomparable atmosphere of the Aegean.

We start on the impressive island of Santorini before setting course for Ios, known for golden beaches, clear bays, and cozy tavernas. Depending on conditions, the route continues to Amorgos – an island with dramatic rock formations and the famous monastery high above the sea.

Next, we sail to Paros or Naxos, two of the most beautiful islands in the Cyclades: lively harbor towns, expansive beaches, and plenty of Greek joie de vivre await you here. Another highlight is Folegandros, a quiet, unspoiled island with spectacular views and one of the most beautiful Choras in the entire Aegean.

Back in Santorini, a journey ends that perfectly combines Cycladic magic, relaxed sailing, and diverse island worlds.

Routenkarte der Segelroute 35
Start / end
Santorini – Santorini
Arrival
Santorini
Group size
Max. 26 guests
Places
Santorini - Ios - (Amorgos) - Paros / Naxos - Folegandros - Santorini

Itinerary

Every sailing trip follows the conditions of nature. The itinerary shown is a non-binding orientation and can change depending on wind and weather.

Individual arrival in Santorini. Perhaps take the opportunity to explore the spectacular volcanic island before boarding – with its whitewashed houses, narrow alleys, and unique views deep into the caldera.

In the early evening, the crew of the RHEA warmly welcomes you on board. With a welcome drink and the first shared dinner on deck, your journey through the fascinating island world of the Cyclades begins.

Against the impressive backdrop of Santorini, your sailing adventure begins. The RHEA anchors off the southern coast of the island, while the steep crater edges rise impressively above the sea.

After breakfast, the captain explains the planned routing for the coming days – always adapted to wind and weather. Sailing is done whenever possible, as this is what gives this journey its special character. Heading for Ios, you enjoy the first hours under sail: the wind, the open sea, and the relaxed atmosphere on board.

Ios delights with a perfect mix of relaxed island feeling, beautiful beaches, and typical Cycladic architecture. Particularly charming is the Chóra above the harbor – a labyrinth of whitewashed alleys, small cafés, blue church domes, and flower-adorned houses.

Away from the lively summer scene, there are numerous quiet spots with wide views over the Aegean. Let yourself drift, enjoy the Mediterranean serenity, and experience the authentic flair of the Cyclades.

Further east awaits Amorgos – one of the most unspoiled and impressive islands of the Cyclades. Rugged mountains, deep blue water, and small bays shape the image of this special island.

The RHEA often anchors in front of the harbor of Katápola. Those who wish can explore the island individually by scooter or quad. High above the sea towers the famous monastery Chozoviotissa, spectacularly built into the rocks and one of the best-known landmarks of the Aegean. The view from up there is as impressive as the special tranquility of this place.

Heading west, the RHEA reaches the island of Paros – known for its lively harbor towns, fertile landscapes, and long history.

The island was already famous in antiquity for its high-quality white marble. Today, vineyards, small fishing villages, and traditional tavernas shape the scene. Enjoy a stroll through the alleys or a relaxed evening by the water with Greek specialties and fresh fish.

A longer leg brings you to Folegandros – a small, unspoiled island with rugged charm and spectacular landscape. The picturesque Chóra is one of the most beautiful in the Cyclades and sits high above the sea on a cliff.

White houses, well-kept squares, and narrow alleys give the place an almost timeless atmosphere. Especially in the late afternoon, Folegandros unfolds its very special magic. Perhaps enjoy a Greek frappé or a glass of wine with a view over the Aegean.

On the last day of sailing, the RHEA sets course back to Santorini. Once again, enjoy life on board, sailing between the islands, and the unique expanse of the Aegean.

An unforgettable moment awaits you as you enter the famous Caldera of Santorini – one of the most spectacular natural backdrops in the Mediterranean. The Captain’s Dinner on board provides a fitting conclusion to your journey.

After a final breakfast on deck, disembarkation takes place. Individual departure or optional extension of your stay in Santorini.

Impressions of your trip

Your sailing yacht

Commissioned in spring 2017, the RHEA — like her sister ship CHRONOS — is with her 1000 m² sail area and 54 m length one of the most beautiful large luxury sailing yachts in the world. “Your private yacht for a limited time!”

RHEA

Cabin equipment

  • Wardrobe
  • Hairdryer
  • Hand and bath towels
  • Air conditioning
  • 230 V sockets
  • Life jackets
Discover the yacht

Deluxe cabin

All prices are per person in a double cabin. Single occupancy supplement: 80%.

Long cabin

All prices are per person in a double cabin. Single occupancy supplement: 80%.

Included services

  • Accommodation on board in the booked cabin category
  • Nautical crew and service on board
  • Sea passage during the trip
  • Full board on board
  • Water sports from on board
  • Water, tea and filter coffee

Not included

  • Travel to and from the yacht
  • Transfers
  • Soft drinks, Nespresso and alcoholic drinks
  • One evening to explore the local cuisine ashore
  • Shore excursions and tips

Dates & prices

Sailing trip in the Cyclades

 – 

Santorini – Santorini

Sailing yacht trip

Yacht: RHEA

Spots still available
Deluxe cabin (p.p.)
€ 4.600,–
Long cabin (p.p.)
€ 4.500,–
Request now

Island hopping from Santorini

 – 

Santorini – Santorini

Sailing yacht trip

Yacht: RHEA

Sold out
Deluxe cabin (p.p.)
€ 4.600,–
Long cabin (p.p.)
€ 4.500,–

Santorini Gourmet Tour in partnership with ZEIT-Reisen

 – 

Santorini – Santorini

Gourmet trip

Yacht: RHEA

Spots still available
Deluxe cabin (p.p.)
€ 4.700,–
Long cabin (p.p.)
€ 4.600,–
Request now

Sailing trip in the Cyclades

 – 

Santorini – Santorini

Sailing yacht trip

Yacht: RHEA

Spots still available
Deluxe cabin (p.p.)
€ 4.600,–
Long cabin (p.p.)
€ 4.500,–
Request now

Island hopping from Santorini

 – 

Santorini – Santorini

Sailing yacht trip

Yacht: RHEA

Spots still available
Deluxe cabin (p.p.)
€ 4.600,–
Long cabin (p.p.)
€ 4.500,–
Request now

Book now

Send us your request without obligation — we will get back to you personally.

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Important information

You can arrive from major airports with the usual airlines. Those wishing to travel more climate-friendly can check options by train or ferry.

The travel price includes: costs for the nautical crew and service, accommodation on board in the booked category, sea transport, full board on board / 1 evening per week to get to know the local cuisine at your own expense, water, tea, filter coffee. The price does not include: arrival and departure, transfers, soft drinks, Nespresso and alcoholic beverages, water sports from the boat, shore excursions, and tips.

In summer it is (almost) always pleasantly warm – although on board above the water it usually remains comfortable – in spring and autumn it is cooler, you sometimes need a sweater, and the weather is more changeable than in summer. The winds of the Mediterranean are as varied as the countries and can be very different depending on the region.

Life on board the Sailing-Classics yachts is very safe and well organised. The vessels meet the highest safety standards and are inspected annually. The captain and helmsman are graduates of a professional maritime college and undergo continuous professional development. The rest of the crew also receive intensive training in how to deal with emergencies. A compulsory safety briefing takes place at the start of every voyage. Furthermore, despite their speed, the yachts sail with remarkable stability – even in heavy weather, hardly any water comes on deck.

Both German and English are spoken on board the Sailing-Classics yachts. The language used amongst the international crew is English, whilst they communicate with guests in both German and English. On the KAIRÓS, we cannot always guarantee communication in German.

Meals on board Sailing-Classics are organised on a full-board basis and are included in the tour price. The day begins with a generous breakfast buffet, followed by a light two-course lunch and coffee and cake in the afternoon. In the evening, the on-board chef prepares a three-course dinner. On the final evening, the festive Captain’s Dinner is the culinary highlight. Once a week, a dinner is held ashore to sample the regional cuisine – this is not included in the tour price. Special dietary requirements and allergies can be catered for if notified in advance.

Sailing-Classics organises shore excursions using the crew’s motorised dinghies. On request, the crew will take you ashore and collect you again free of charge – simply let the team know in good time. In addition, in many sailing areas, the crew organises guided shore excursions with a local guide or accompanied by a crew member. The price per participant is communicated in advance and charged to your on-board account. Of course, you are also welcome to explore the surrounding area on your own.

The cabins on board the Sailing-Classics yachts are comfortable and practically furnished. Each cabin has its own en-suite bathroom with a toilet and shower cubicle, individually controlled air conditioning, a wardrobe, a hairdryer, and hand and bath towels. 230-volt sockets are available for charging electronic devices. A reusable water bottle is provided in every cabin and can be refilled at the water dispenser in the saloon.

At Sailing-Classics, you’re warmly invited to get actively involved in sailing – no prior experience or sailing licence required. You can help set and trim the sails, take the helm yourself, or lend a hand with other tasks on deck. The crew will be happy to explain the basics of sailing to you, show you how radar navigation works on the bridge, or give you a tour of the engine room. Those who prefer to relax can simply enjoy the passing scenery – the motto is: ‘Everything is possible, nothing is compulsory.’

To cancel your sailing holiday with Sailing-Classics, please send your cancellation request by email to info@sailing-classics.com. Written notification is required so that the cancellation can be processed officially. Depending on when the cancellation is made, Sailing-Classics’ tiered cancellation terms and conditions will apply. We strongly recommend that you take out travel cancellation insurance to protect yourself financially.
On-board ABC – everything you need to know

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