20 by the glassBolgheri
The village wine bar of Bolgheri, established 1965 just off the Cypress Avenue. Full Bolgheri DOC roster on bottle and a long-standing relationship with the founding producers of the appellation.
The list: Bolgheri-specialist list with the full classified producer roster including Sassicaia, Ornellaia, Masseto, Le Macchiole and Grattamacco; vertical flights by reservation
Pours: Bolgheri Superiore DOC, Sassicaia, Toscana IGT
18 by the glassChianti Classico
Tasting bar on Greve's central piazza specialising in producers from the Greve and Panzano sub-zones. Sommelier-curated flights match Chianti Classico tiers with classic Tuscan pairing plates.
The list: Chianti Classico-led list of 250 producers with by-the-glass selections across Greve and Panzano area estates; tasting flights of 3 to 6 wines
Pours: Chianti Classico Gran Selezione, Sangiovese di Greve, Vin Santo del Chianti Classico
22 by the glassVernaccia di San Gimignano
San Gimignano wine bar focused on Vernaccia di San Gimignano DOCG and the surrounding red appellations. Vaulted cellar room with a structured glass and bottle programme.
The list: Vernaccia-specialist list with full DOCG producer roster plus San Gimignano Rosso and Toscana IGT; flights of Vernaccia from different sub-zones available
Pours: Vernaccia di San Gimignano DOCG, San Gimignano Rosso DOC, Vin Santo San Gimignano
12 by the glassSanto Spirito, Florence
Tiny Santo Spirito wine bar in a former cellar, sister venue to Il Santo Bevitore next door. Tuscan-favoured list with small artisan producers; standing-room counter and a handful of bar stools.
The list: 200 mostly Tuscan labels with rotating six reds and six whites by the glass, sourced from small under-the-radar producers; complimentary snack with each pour
Pours: Chianti Classico, Sangiovese Toscana IGT, Bolgheri Superiore
20 by the glassOltrarno, Florence
Wine shop and bar facing the Pitti Palace, focused on small-production handcrafted Tuscan wines. Tasting menus engineered around the bottle list; dinner service runs to 22:30.
The list: Hand-selected small-production Tuscan-led list with high-end vertical verticals available; structured tasting menus pair courses with wine across all price tiers
Pours: Brunello di Montalcino, Chianti Classico Gran Selezione, Bolgheri Superiore
25 by the glassSan Lorenzo, Florence
Behind the San Lorenzo market under a colonnade, this 19th-century enoteca is run by the Migliorini family in its fourth generation. Wine by the glass alongside crostini and made-to-order panini.
The list: Florence's oldest operating wine shop with 25 bottles open daily; Tuscan-heavy by-the-glass list rotating with seasonal selections from grower producers
Pours: Chianti Rufina, Tuscan house wine carafe, Vin Santo del Chianti