Kimolos is the kind of island people leave reluctantly: small, slow and mostly empty, with a harbour village, a hilltop Chorio and coves you can often have to yourself. Many visitors use it as a quiet base next to Milos, and this crossing is how they add Santorini to the end of a western Cyclades trip without going back to Piraeus first.
It is a direct line, but not a quick one. The only ship on it belongs to Fast Ferries, a conventional operator, and the crossing takes around four hours. The upside is price: the lowest adult fare on Ferryhopper was €13 when we checked, less than many much shorter high-speed hops cost in summer.
The limitation is frequency. Ferryhopper lists sailings on 1 to 4 days a week, and in its monthly table of last year's data each Fast Ferries entry shows one to three sailings a week, with a few months marked as having no data. That means the ferry decides which day you leave Kimolos, and you should confirm it before booking your last nights on the island or your first nights on Santorini.
Plan the Santorini end carefully too. You arrive at Athinios, the island's main port under the caldera cliffs, where the single road up can clog when several ships land together. If you are flying out of Santorini (JTR) soon after, leave a generous buffer: with so few sailings a week, there is no later boat to catch if this one is held up.