This crossing takes you from one end of the Cyclades beach scene to the other: from the shallow turquoise bays of Koufonisia in the Small Cyclades to the volcanic coastline of Milos in the south-west, some 55 nautical miles away. It is a popular way to finish a trip that started in the Small Cyclades, because Milos has an airport and frequent boats back to Piraeus.
Only Seajets sails the route, and only between April and October. How often depends heavily on the month. Ferryhopper's monthly table for Koufonisia to Milos, based on last year's data, shows one sailing a week in April, six days a week in May, five in June, three in July, two in August, and a daily boat in September and October. Midsummer, oddly, is the thinnest time.
It is a long ride for a fast boat, about 4 hr 20 min at best and up to 5 hr 20 min in June and July, and fares are high: Ferryhopper listed one adult from €107.70, with monthly prices up to €116.70. Our older route data quoted fares from €40 and a four-hour crossing; Ferryhopper's figures do not support the €40 fare, so use the booking page for the real price on your date.
Koufonisia is a walk-everywhere island, so getting to the boat is simple. The effort goes into choosing the right day. If the direct boat does not run when you need it, Naxos and Paros both have ferries to Milos and short links from Koufonisia.