The proven small-group upgrade: a twenty-guest cap, a real meal and an open bar, with 4,175 reviews behind it.
from $128 per person, live price on the listing
Check Price & Availability →Opens the operator's official listing with live dates. Book there; nothing is charged on this site. Free cancellation up to 24 hours before.
The question this boat answers is the one most people ask after reading about the classic: what does it cost to do the same evening with fewer people? Here the answer is $128 and a deck capped at twenty. The galley plates a fresh Greek meal instead of running a grill line, the open bar includes a cocktail, and 4.8 across 4,175 reviews says the upgrade is real rather than cosmetic. It also holds this site's only choice of departure: the classic sunset run, or a morning sail that trades the famous light for empty swim stops.
With twenty guests, the rhythm changes. Boarding is quick, there is no line at the ladder, and the swim stops stretch out because nobody is queuing to get back on deck. The route holds the caldera anchors, the hot-springs swim included, and the meal arrives plated rather than queued for: fresh Greek dishes with the open bar pouring wine, beer, soft drinks and a cocktail alongside.
The morning departure is the sleeper option. Same boat, same food, same swims, but the caldera is glassy, the stops are empty of other boats, and you are back by early afternoon with the evening free. If you have seen the sunset from Oia already, the morning sail is arguably the better sail. Sunset departures track the season's sunset hour; hotel pickup is included either way.
This is the boat for travelers who want the small-deck experience with big-fleet reliability: 4,175 reviews is an unusual volume for a twenty-guest product, and the 4.8 across them is the reassurance the premium buys. It fits couples, families with teens, and anyone allergic to crowds but wary of tiny operators.
It is not the cheapest way onto the water; the $75 classic exists for that, on a much fuller deck. And it is not private: twenty guests is intimate, not exclusive. If the whole boat needs to be yours, the private Wind Spirit charter prices per group and starts making sense from about six people. Like the flagship, this listing shows a sell-out badge in season, so it books out ahead in July and August.
Sunset if it is your first caldera sail or the light is the point. Morning if you want the swim stops without another boat in sight, calmer water, and your evening kept free. Same boat, meal and bar either way.
Wine, beer and soft drinks plus a cocktail, alongside a fresh Greek meal from the galley. It is the only boat on this site with a cocktail in the standard bar.
It is the listing's stated maximum. An earlier version of the listing said 16; the current one says 20, and that is the figure we print. Either way it is less than half the flagship's deck.
Free cancellation up to 24 hours before departure, full refund. Weather calls are the operator's, and a weather cancellation reschedules or refunds in full.
About 5 hours · Transfer included · Sunset Oia
The boat itself is the upgrade here: a Lagoon 560, one of the biggest production sailing cats afloat, sailed with a 20-guest cap so the trampolines never fill. The Greek BBQ menu is cooked on board rather than reheated, white wine and beer flow with it, and round-trip hotel transfer is folded into the price rather than sold as an extra.
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