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From Santorini to Rhodes: sailing through fairytale scenery

Greece:

Dodecanese

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

August

Suitable for travellers:

> 5 years

Boarding from:

Santorini Harbour

What's included

Cancellation policy

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Organised by:

Riccardo C.

Member since 2015 -

Private

Italian

English

This experience, in a nutshell

This is a trip not to be missed! Santorini, from where we will set sail, is magical: the island is founded on a caldera formed by a volcano that collapsed in the sixteenth century BC that forever shaped its rugged landscape. High up, all around the huge bay, perched on the steep black cliff stands an amphitheater of cube-shaped white houses gathered in two townhouses, Oia and Fira, . From these cities, the view extends to the magical sea of Greece, the small islands to the west and the beaches made of black, red and white volcanic stone.

Leaving the magical Santorini, before arriving in majestic Rhodes, we will touch a series of delightful, picturesque islands:

Anafi, tiny, quiet, lying on a vast horizon, is a place where time seems to have stopped: visiting it you can admire fantastic views typical of the Ciladi.

Astypàlea, the butterfly-shaped island, offers breathtaking views from la Hora, its tiny center: a group of whitewashed houses dominated by a medieval fortress.

Tilos, with its warm amber mountains, is home to a very rich fauna and in its blue waters of its many bays it is easy to meet sea turtles.

Driven by the Meltemi, we will arrive at the largest island of the Dodecanese: Rhodes and its capital, Rodos. Famous in ancient times for its colossus overlooking the port of Mandraki, it is spectacular and steeped in a glorious history. In all eras it has always been an important trading center and by 400 BC it was already divided into three capitals: Rodos, the current capital, Lindos and Kamiros. The latter are still archaeological sites in excellent condition. Here the crusader knights took refuge to resist the revival of the Saracen warriors and built the imposing castle that still dominates the city today. The historic centre of Rodos is dominated by churches, a mosque and theGrand Master's Palace.

The Mandràki, the ancient port where we will moor, is still surrounded by picturesque windmills. Looking out you can see the Turkish coast in the distance, and walking along its piers you seem to see the fast galleys ready to attack those of Saracen pirates.

No Departures available

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16+

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Boat & Classes of Service

Jeanneau Sun Charm 39 - 1990

Type

Sailboat

Length

12 m.

Toilets

2

Cabins

3

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10+

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Our itinerary

Our trip starts here:

Santorini Harbour.

Check-in: 6:00 PM

Our trip ends here:

Rhodes.

Check-out: 6:00 AM

Our itinerary


Leaving the magical Santorini, we will touch a series of delightful, picturesque islands: Anafi, tiny, quiet, lying on a vast horizon, is a place where time seems to have stopped. Visiting it you can admire fantastic views typical of the Ciladi. Astypàlea, the butterfly-shaped island, offers breathtaking views from la Hora, its tiny center: dominated by a medieval fortress. Tilos, with its warm amber mountains, is home to a very rich fauna and in its blue waters of its many bays it is easy to meet sea turtles. Also very interesting is Chalki, a tiny but delightful island, surrounded by beautiful bays. The city of Rhodes is spectacular and steeped in a glorious history. Lindos, one of the ancient capitals of the island, is beautiful. s

The itinerary may be subject to changes due to weather conditions and/or technical or logistical reasons, in order to ensure safety and a pleasant sailing experience for all participants.

Frequent questions

The organiser reviews

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Organised by:

Riccardo C.

Member since 2015 -

Private

Italian

English

4.6/5

out of

31

reviews

Skipper

Boat

Destination

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From Sicily to Greece crossing the Strait of Messina

07/6/2025

Barbara B.

-

Hungary

Skipper is not speaking English at all, however he marked language knowledge on his profile . The communication issues made strange situations on the boat. Boat wasn't 100% clean when we were onboarded and we were also not allowed to use the inside showers on the boat (we had no stops in Ports with shower opportunities during the cruise )
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Magical sailing crossing from Procida to the Aeolian Islands

06/24/2025

Annamaria L.

-

Italy

Riccardo is an experienced skipper, he loves sailing and made us experience beautiful emotions in fantastic places. He involved everyone in the management of the boat, even me who was completely inexperienced.
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Sailing between Argentario, Palmarola, Ponza, Ventotene and Procida

06/15/2025

Silvia G.

-

Italy

Riccardo is an experienced and passionate sailor, who shares his love for the sea and sailing with great enthusiasm. This is an ideal experience for those looking to enjoy an authentic sailing holiday. A good spirit of adaptability and flexibility is recommended to fully appreciate this wonderful adventure. Not recommended for those who are completely new to sailing.
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From the wonders of Sardinia to those of Menorca, the Balearics

06/22/2023

Adam G.

-

Poland

I really enjoyed the cruise with Riccardo. He is an experienced sailor and I trusted him, which is very important, especially if you have make a long crossing between islands, as we did. Riccardo took us to a lot of pretty places, and the trip was filled with beautiful moments like eating dinner together with the entire crew while enjoying the sunset in a lovely bay at anchor, or swimming in the sea during the day to cool yourself down. La dolce vita. The boat is well-equipped and comfortable, and the captain goes out of his way to make everyone comfortable. Obviously there were also some misunderstandings, but honestly, that is to be expected in a group of people traveling and living together for a week, and I think all quarrels which arose were handled properly in the end. Overall, it was a great experience. Thank you, Riccardo!

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