header cover
sailsquare logo

From Santorini to Rhodes: sailing through fairytale scenery

Greece:

Dodecanese

Duration:

6 days - 7 nights

Max number of passengers:

6 people

Available:

-

Suitable for travellers:

> 5 years

Boarding from:

Santorini Harbour

What's included

Cancellation policy

avatar image

Organised by:

Riccardo C.

Member since 2015 -

Private

English

Italian

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

experience image 0experience image 1
experience image 2
experience image 3

16+

Show all

Boat & Classes of Service

Jeanneau Sun Charm 39 - 1990

Type

Sailboat

Length

12 m.

Toilets

2

Cabins

3

boat image 0boat image 1
boat image 2
boat image 3

10+

Show all

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.

What's included in the price

•

Boat equipment and facilities

    Final cleaning

    Tender and outboard

•

Onboard staff

    Skipper

What you'll have to pay during the experience

Below are the additional expenses you will incur during the experience.

Common Fund

€100 - €250 Per person

The common fund will be created at the time of boarding. The fuel charge will be calculated on the basis of the cost of 5 litres of diesel for each hour of motor navigation carried out. Obviously we will try to sail as much as possible under sail!

    Galley

    Food for the skipper

    Alcoholic drinks

    Mooring fees

    Embarkation and disembarkation mooring fees

    Fuel (boat/tender)

What's NOT included in the price

Below are the services that are not included in the price of the experience, including any available optional services that you may pay directly to the organiser (we advise you to inform the organiser prior to departure in case you wish to purchase such services and arrange the payment terms directly with him).

Excluded

    Bedding kit

    Towels kit

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

avatar image

Organised by:

Riccardo C.

Member since 2015 -

Private

English

Italian

4.4/5

out of

35

reviews

Skipper

Boat

Destination

avatar image

Mykonos, the delightful little Cyclades and magical Santorini

08/3/2025

Ana D.

-

Spain

It has been fantastic it has exceeded my expectations
avatar image

Great sailing from Athens to Mykonos in the Cyclades

07/27/2025

Alessio L.

-

Belgium

Riccardo is a good person but the boat was not prepared to welcome guests, particularly in terms of cleanliness and order. Some episodes, which by an expert person should and could have been predicted and dealt with calmly, generated unnecessary anxiety (lack of fuel in the tender, staysail rigged at the last minute in critical circumstances, disorderly mooring and unmooring maneuvers, instructions to the crew not given sufficiently in advance and clarity, etc.). A general perception of approximation has generated a feeling of insecurity and discomfort which has unfortunately negatively affected the serenity and enjoyment of the holiday.
avatar placeholder

Great sailing from Athens to Mykonos in the Cyclades

07/27/2025

Marco P.

-

Italy

I participated in a week on a sailing boat with high expectations, but unfortunately the experience was disappointing in many ways. First of all, the spaces on board were extremely limited: I had to sleep outside every night due to the lack of comfort inside and I was not the only one to do so. In addition, the boat turned out to be quite dirty and poorly maintained, which negatively affected the stay. The skipper, although probably with years of navigation behind him, seemed to me not very suitable for this type of experience. In addition to obvious communication difficulties (he often did not hear), he completely lacked initiative. He seemed more on vacation than us: he didn't help with daily activities, and in general he didn't make himself useful, behaving more like a guest than like a person on board. From a technical point of view, I didn't feel particularly confident. The skipper, in my opinion, no longer had the physical strength necessary to manage the maneuvers: in seven days we opened the sails only twice, and always with great caution, out of fear. On a sailing holiday, you would expect to... sail. A real shame, because the company and the sea were wonderful. But with different and more professional management, the experience could have been totally different. I hope that the organization will think seriously about these aspects.
avatar placeholder

Athens, Delphi, Patras and the excitement of the Corinth Canal

07/20/2025

carmen G.

-

Spain

The trip was very nice, we were able to visit Delphi which for me was the best part of the trip. Riccardo is a good person and a good sailor, but he hardly speaks English or French, which was a problem when it came to communicating with us and with the marinas. He could not understand his instructions and became very nervous when performing the maneuvers. I should have specified that you need some experience to travel with him. He gets very nervous and starts shouting in Italian. He is quite old, I think he would have to sail alone in Italy, which is his comfort zone. The boat is small ideal for 4. To be honest, I don't think I'll travel with him again. But Greece is wonderful

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964