Santo Wines Evening Sunset Tastings ★ 4.4
30 by the glassPyrgos
Santo Wines's cliff-top facility above Pyrgos operates evening tasting flights through sunset and into the night, with caldera-view terraces seating hundreds of visitors.
The list: Santo Wines runs evening tasting flights into the late evening hours, with caldera-view terraces serving the cooperative's full Assyrtiko, Nykteri and Vinsanto range. The cooperative seats hundreds across its terraces, and sunset slots fill weeks ahead in the high season.
To Ouzeri Tasting Bar ★ 4.2
15 by the glassFira
To Ouzeri in Fira's Fabrica Town pairs traditional Greek ouzeri small-plate mezze with a respectable by-the-glass Santorini wine list. The atmosphere is more local than the caldera-rim venues, and the late hours make it a reliable post-dinner wine stop.
The list: To Ouzeri is a traditional ouzeri-style bar with a strong by-the-glass wine list focused on Santorini Assyrtiko, Aidani and PGI Cyclades blends alongside the namesake ouzo and tsipouro. A useful late-evening venue for an Assyrtiko alongside small plates of regional mezze.
Kapari Wine Restaurant ★ 4.4
25 by the glassOia
Kapari Wine Restaurant is one of Oia's longest-established wine-focused dining rooms, with a list weighted toward Santorini producers and a by-the-glass programme that supports comparative tasting.
The list: Kapari maintains an extensive Santorini and Greek wine list with a particular focus on the island's Assyrtiko producers. The by-the-glass programme runs late into the evening on summer nights, and the restaurant's wine staff are practised at producer-comparison flights.
Mr. E Cocktail Bar ★ 4.0
10 by the glassOia
Mr. E in Oia combines a cocktail programme with a curated music environment, making it one of the few listening-bar adjacent venues in the village. The wine selection is limited but covers Santorini Assyrtiko with respectable focus.
The list: Mr. E is primarily a cocktail bar but maintains a respectable wine list with several Santorini Assyrtiko options by the glass. The bar has a curated music programme with vinyl-leaning playlists and live DJs, giving it a listening-bar atmosphere uncommon in Oia.
Tropical Bar Fira ★ 3.9
8 by the glassFira
Tropical Bar's location on the Fira caldera path with live music makes it one of the more atmospheric drinking venues in the village. Wine is secondary to the music programme but the list is sufficient for a relaxed evening glass.
The list: Tropical Bar in Fira's caldera path maintains a small by-the-glass wine list alongside its cocktail and music programme. The venue is known for live music evenings and DJ sets and has a relaxed listening atmosphere.
Kira Thira Jazz Bar ★ 4.1
8 by the glassFira
Kira Thira has operated as a jazz bar in Fira for decades and has a listening-bar identity. The wine list is small but reliable for an Assyrtiko glass during the music programme.
The list: Kira Thira is a long-established jazz bar in Fira with a small by-the-glass wine list alongside cocktails. The venue's jazz focus and a sequence of evening sessions make it a genuine listening-bar destination in central Fira.