The straight answer
Yes, for the sunset and the wine. No, not for a whole trip. That is not a hedge; it is what Greece's own list says when you count it. Santorini appears exactly twice in 32 entries: watching the caldera sunset, which currently leads the list, and tasting volcanic wines at a winery. The other thirty entries are busy arguing that Greece mostly happens somewhere else.
Both Santorini entries are real. The island is the rim of a volcano that erupted around 3,600 years ago, and the sunset entry works because you are not looking at the sea, you are looking down into a flooded crater from the top of its wall. No other Greek island offers that geometry. The winery entry is quietly the better insider pick: assyrtiko vines grown in volcanic ash, trained into low basket coils against the wind, producing a wine you can only make there. An evening on the caldera rim and a morning at a winery is Santorini done completely.
What the crowds change, and what they don't
The famous problem is real: in high season the sunset viewpoints in Oia fill hours before the sun goes anywhere, and the lanes behind them turn into a slow queue with a view. The pattern from the case for doing the famous thing early applies in mirror image here: the entry has a timestamp, and the timestamp has a crowd attached. Shoulder season blunts it. So does watching from Imerovigli or Firostefani on the same caldera wall instead of the Oia postcard spot, since the crater does not care which town you stand in.
What crowds do not change is the price of treating Santorini as the whole trip. It is one of the most expensive corners of the Greek islands, and after the second sunset you have seen the trick. The island's two entries are dense; they are also finished in two nights.
What the other thirty entries argue
Read the rest of the Greek list and a different trip assembles itself. Milos, one ferry away, holds the entry for swimming at a beach you can only reach by boat. Crete carries four: the Samaria Gorge hike, the Minoan palace of Knossos, dakos and raki in a Chania taverna, and learning to make dolmades in a Cretan kitchen. On the mainland, Meteora's monasteries sit on top of rock pillars, Delphi hangs on its mountain slope, and Epidaurus still stages performances in its ancient theatre. Monemvasia and Hydra hold the hidden-gem entries, one a fortress town, one an island with no cars at all.
None of those are consolation prizes for people who could not afford Oia. They are the bulk of the list, and the list is the closest thing we have to a map of what actually holds up.
The verdict, in itinerary form
Give Santorini two nights: arrive, winery in the daylight, caldera at dusk, leave. Spend what you saved on the ferry onward, to Milos if the boat-only beach entry pulls you, or to Crete if the food entries do. You will have done both of Santorini's must-dos properly, skipped the part of the island that exists mostly to be photographed, and used the other thirty entries the way a ranked list is meant to be used: as the argument for where to go next. If you disagree when you get back, the vote buttons are on the list. That is what they are for.