Syros and Milos make a rewarding pair. Ermoupoli, the capital of Syros and of the whole Cyclades, is a real working town of marble squares, mansions and a busy harbour, while Milos is all about the coast: volcanic rock in strange colours, sea caves and beaches you reach by boat. Travelling from one to the other takes you from the centre of the island group to its south-western edge.
The direct link is a single conventional ship. Ferryhopper lists only Blue Star Ferries on this crossing, three days a week in every month of last year's data, and the ship works its way through other islands on the way, so it is not a quick trip. In spring its sailings took 4 hr 30 min; in the rest of the year they took about 7 hr 30 min. The reward is a low fare, from €12.50 for one adult when we checked, and a long, easy day on deck.
If you have the time, the direct ship is simple: board in Ermoupoli, arrive in Adamas, no connections to worry about. If you would rather spend the day on a beach, look at splitting the journey instead. Syros has quick, frequent boats to Paros, and Paros has high-speed sailings to Milos; on some days that is the faster way.
Our older route data described a 2-hour high-speed crossing from €15 with Seajets, Golden Star and Aegean Sea Lines. Ferryhopper's dated figures do not show any of those operators on this direction, so we have not used that data here.