Imerovigli Caldera Wine Lounges (cluster) ★ 4.2
18 by the glassImerovigli
Imerovigli is the quieter middle section of the caldera rim between Fira and Oia. The hotels along the caldera path operate as wine lounges with Santorini-focused by-the-glass programmes, providing a calmer evening wine experience than the busy village centres.
The list: Imerovigli's caldera-side hotels (Astra Suites, Aegean Plaza-affiliated venues and the Grace Santorini lounge among others) maintain by-the-glass wine programmes weighted toward Santorini Assyrtiko, serving as lounge venues into the late evening with calmer atmospheres than the busier Fira or Oia central strips.
Oia Caldera-Rim Hotel Lounges (cluster) ★ 4.5
20 by the glassOia
The Oia caldera-edge hotel lounges represent the premium tier of Santorini wine drinking, with curated Santorini-focused lists, sommelier service and the sunset view at the western tip of the island. Open to non-staying guests by booking.
The list: The cluster of Oia caldera-edge hotels (Andronis, Canaves Oia, Katikies, Mystique among others) maintain comprehensive Santorini-focused wine programmes in their hotel bars and lounges, with by-the-glass and bottle service at sunset and into the evening.
Santo Wines Vinsanto Tasting Room ★ 4.5
8 by the glassPyrgos
Santo Wines offers the most accessible dedicated Vinsanto tasting on the island, with multiple ageing tiers poured side by side. While not fortified in the strict sense, Vinsanto fills the dessert-and-sweet-wine specialist role on Santorini.
The list: Santo Wines runs a dedicated Vinsanto-focused tasting programme covering 4-year, 12-year and longer-aged Vinsanto from the cooperative's library. Vinsanto is Santorini's PDO sweet wine, a sun-dried passito-method wine and the closest Santorini analogue to fortified wine specialist programmes elsewhere.
Estate Argyros Vinsanto Library ★ 4.7
6 by the glassEpiskopi Gonia
Estate Argyros's library Vinsanto programme is a destination for sweet-wine enthusiasts visiting Santorini. The estate has held back significant portions of each Vinsanto vintage for extended ageing, and the library flight covers multi-decade Vinsanto in a single sitting.
The list: Estate Argyros holds an extensive vertical library of Vinsanto, with bottlings stretching back several decades available in the estate's senior tasting flights. Booking direct is essential for the long-aged library pours.
Canava Roussos Heritage Vinsanto Tasting ★ 4.4
5 by the glassMesa Gonia
The Canava Roussos heritage cellar at Mesa Gonia is an evocative Vinsanto tasting setting, with the historic family canava framing the long-aged sweet wines. A slower, quieter Vinsanto experience than the high-volume cooperative format.
The list: Canava Roussos at Mesa Gonia, founded in 1836, holds heritage Vinsanto stocks dating back through the family's multigenerational ownership. Tasting at the canava covers current-release alongside older library Vinsanto in the historic stone-built cellar.
Santo Wines Extended Evening Tasting Sessions ★ 4.3
20 by the glassPyrgos
Santo Wines's extended-hours sessions through the high season allow late-evening cellar door tastings that would not be possible at smaller estates.
The list: Santo Wines runs late-tasting sessions through the high season with extended hours through sunset. The cooperative's flight format covers Assyrtiko, Nykteri and Vinsanto with extensive volume capacity, and the late slots are easier to book than the headline 18:00 to 19:00 window.