header cover
sailsquare logo

Log in

Route to the South: The Small Cyclades and spectacular Santorini

Greece:

Cyclades

Duration:

7 days - 7 nights

Max number of passengers:

6 people

Available:

August - September

Boarding from:

Paros

What's included

Cancellation policy

avatar image

Super!

Organised by:

Alessandro B.

Member since 2012 -

Organisation

Italian

English

This experience, in a nutshell

We will depart from Paros (Parikia or Aliki) and let the wind carry us to the heart of the Cyclades:

Paros ➡️ Small Cyclades: We will start with the peace of Iraklia and Schinoussa, where silence reigns and the water is emerald. They are the perfect islands to forget stress and take your first dips.

Koufonissi: Often called "the pool of the Aegean", it will enchant us with its sea caves and fine sandy beaches.

Amorgos: The island of the "Big Blue". Here the sea turns a deep blue and we will visit the spectacular Monastery of Chozoviotissa, set in the rock overlooking the sea.

Anafi: One of the rarest and wildest destinations. It is a remote island, far from mass tourism, where time seems to have stopped.

Santorini: We'll enter the Caldera by boat, a unique volcanic scenery in the world, with the typical white houses crowning the dark cliffs.

Ios: We'll end the trip in Ios, famous for its spectacular bays (such as Manganari) and its lively Chora, perfect for the last evening together.

The itinerary may be subject to change, depending on weather conditions and/or for technical or logistical reasons, in order to ensure safety and pleasant navigation for all participants.

Starting from

€765

7 days - 7 nights

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

8+

Show all

Boat & Classes of Service

Ocean Yachts Ocean Star 48.1 - 2007

Type

Sailboat

Length

15 m.

Toilets

3

Cabins

4

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

9+

Show all

Our itinerary

Our trip starts here:

Paros.

Check-in: 5:00 PM

Our trip ends here:

Ios.

Check-out: 7:00 AM

Our itinerary

A sailing cruise, with skipper, dedicated to those who love comfort and total relaxation We will sail in the heart of the Cyclades islands to visit every corner of this beautiful corner of Greece.


The Greek islands will give you unforgettable landscapes, unspoiled bays, characteristic villages and wonderful archaeological sites, long swims, beautiful walks and the wonderful colors of the Mediterranean.


We set sail to discover Santorini Iraklia, Schinoussa, Kufounissi, Santorini, and the other pearls of this Greek archipelago and then arrive in Ios. A cruise dedicated to total relaxation among the best of the Cyclades.

Evenings in the bays or marinas of the villages that we will meet along the way.

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

    Bedding kit

    Towels kit

•

Onboard staff

    Skipper

•

Taxes, fees and moorings

    Embarkation and disembarkation mooring fees

What you'll have to pay during the experience

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

Common Fund

€150 - €180 Per person

Initial payment: Upon boarding we will collect € 100 each to start shopping and the first full tank. What the case includes: Galley: Food, drinks, water and boat hygiene products

    Galley

    Food for the skipper

    Alcoholic drinks

    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

    Meals/drinks consumed ashore

Frequent questions

The organiser reviews

avatar image

Super!

Organised by:

Alessandro B.

Member since 2012 -

Organisation

Italian

English

4.8/5

out of

82

reviews

Skipper

Boat

Destination

avatar placeholder

Milos to Paros: the best of the Cyclades

09/27/2025

Rocco G.

-

Switzerland

Alessandro is a legend, an excellent cook and tries to fulfill customer requests in the best way always taking into consideration the safety and comfort of the crew. You feel like you care about delivering the best experience possible. We had bad luck with the weather, but despite this it was an adventurous and nice week.
avatar image

Milos to Paros: the best of the Cyclades

09/23/2025

Massimiliano B.

-

Italy

Alessandro, in addition to being a dispenser of seafaring anecdotes and an excellent "skipper" was above all a very nice travel companion.
avatar placeholder

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

09/15/2025

Florian H.

-

Germany

Great trip & great skipper!
avatar placeholder

Astypalaia, Anafi and Santorini: the pearls of the Southern Cyclades

09/3/2025

Remy L.

-

Netherlands

We had an amazing week with Alessandro. He was very friendly, helpful and made our holiday very relaxing. 10/10 would recommend.

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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