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Paros is not a base for most well-known charter companies and I would not recommend it as a starting point of your cruise in June. One-way Kalamaki to Santorini (the "new" marina on the southern coast of the island) is a better option from a sailing viewpoint (mostly reaching to running), but you will pay extra (cost about €300). Milos is very interesting as an island with beautiful landscapes, but it lies too much to the West. On the other hand it has common features with Santorini, with the latter being much more spectacular. When going south from the mainland, the usual route is along the islands of Kythnos, Serifos and Sifnos (Vathy bay is very well protected). If you call on Folegandros, just know that they have recently improved the quay and you will not have to compete against local fishermen for a berth (definitely go up to visit the "Hora" on the cliffs). Before you reach Santorini there is a possibility of stopping over for a swim at Manganari bay on the southern coast of Ios.
I wish you fair winds and don't forget to report back positive and negative aspects of your journey!
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