12 by the glassOia
The hilltop aperitivo terrace at Canaves Sunday in Oia, opened in 2023 as the sunset-focused outpost of the Canaves Oia collection. By-the-glass Santorini whites and Cycladic vermouth flights front a sweeping caldera view.
The list: Caldera-view aperitivo terrace pouring Santorini Assyrtiko, sparkling, vermouth and signature cocktails. Sommelier-curated by-the-glass program weighted to Santorini and Cycladic PDOs.
Pours: Santorini PDO Assyrtiko, Greek sparkling, Mavrotragano red
14 by the glassOia
The private wine balcony at Canaves Oia Suites overlooks the caldera at sunset. The sommelier serves curated Santorini flights and library Vinsanto in a one-table-at-a-time format for hotel guests and limited outside diners.
The list: Private balcony wine experience with a sommelier-led list weighted toward Santorini Assyrtiko, Vinsanto and notable Greek reds. Vertical Sigalas and Argyros flights available on request.
Pours: Sigalas Assyrtiko, Argyros Vinsanto, Mavrotragano blends
16 by the glassOia
The west-facing terrace lounge at Canaves Oia Epitome, opened on the Foinikia cliff in 2018. The bar program centres on local PDO Santorini wines by the glass with cocktails built around estate-aged Vinsanto.
The list: Caldera sunset bar pouring Santorini sparkling, Assyrtiko and Aidani by the glass alongside a curated Greek wine list and signature cocktails using Vinsanto reductions.
Pours: Santorini sparkling Assyrtiko, Aidani-Assyrtiko field blend, Vinsanto Old Fashioned
22 by the glassPyrgos
The lower cellar bar of Santo Wines, in the Pyrgos cooperative complex above Athinios. Sit-down tasting flights walk through the full five-tier portfolio with explanations of the kouloura basket-vine system from cooperative winemakers.
The list: The lower bar pouring all five tiers of the SantoWines portfolio including PDO Santorini, single-vineyard Grand Reserves and library Vinsanto verticals.
Pours: Santo Wines Grande Reserve Assyrtiko, Santo Wines Vinsanto 12 Years, Santo Wines Aidani
8 by the glassVourvoulos
The minimalist cellar bar at Vassaltis Vineyards in Vourvoulos opens directly onto 14 hectares of estate kouloura vines. Sit-down flights of the limited boutique production are guided by the cellar team.
The list: Cellar bar pouring the Vassaltis estate range including Nassitis single-vineyard Assyrtiko, the orange-skin-contact Plethora and limited Aidani bottlings.
Pours: Vassaltis Nassitis Assyrtiko, Vassaltis Plethora, Vassaltis Aidani
14 by the glassEpiskopi Gonias
The cellar bar of Estate Argyros in Episkopi Gonias holds an extensive old-vine Vinsanto library, with verticals stretching back roughly three decades.
The list: Sit-down cellar bar pouring the full Estate Argyros range with deep Vinsanto verticals back to the 1990s and rare bottlings from the family's 200-year-old ungrafted vine library.
Pours: Argyros Cuvée Monsignori Assyrtiko, Argyros Vinsanto 20 Years, Argyros Mavrotragano
