Inside Montalcino's 14th-century fortress, founded 1980 by Mario Pianigiani and Marzio Giannelli. Five-glass Brunello flights, blind tastings and panoramic ramparts.
The list: Wide-ranging Brunello di Montalcino vertical with around five regular tasting flights and five top-shelf flights, plus cheese, salumi and pasta pairings
Tip: Climb the fortress staircase before the tasting; the panoramic ramparts run around the medieval walls and overlook the Val d'Orcia.
Address: Piazzale Fortezza 9, 53024 Montalcino, Italy, Tuscany
Front-row table service across from the Duomo and Baptistery, a record store upstairs and Italian craft beer and wine pours below. Closed Mondays.
The list: Italian craft beers, regional cured meats and pecorino plates plus a small but well-chosen Tuscan red and white list
Tip: Vinyl shopping while drinking; the front-row view of the Baptistery turns golden after sunset.
San Frediano cocktail spot run by Neri Fantechi and Julian Biondi. Tiny brick-walled room turns club-like after midnight when the DJ takes over.
The list: Cocktail-led, with a tight by-the-glass list of Tuscan small producers as supplement
Tip: The Soul Warmers section of the menu is the bar's signature; arrive early to claim a wooden table by the brick wall before the DJ starts.
Florence's longest-running club, opened 1981 near the airport. International techno and house DJs on weekends, with a wine bar room for slower pours.
The list: Cocktails and Italian craft beers; modest by-the-glass list
Tip: Plan a taxi back; Tenax sits near Florence airport and runs latest of any Tuscan club.
Florence's original speakeasy, hidden behind a faint blue light on Borgo Tegolaio. Forty-five seats, candlelight, no standing and a strict reservation policy.
The list: Cocktail-led; a small reserve wine list with Tuscan and Champagne bottles
Tip: No walk-ins; ring the doorbell only after a reservation made through the bar's site, otherwise expect to be turned away.
Dario Cecchini's upstairs steak house in Panzano. Single seating, communal table, parade of beef courses paired with house red and Panzano bottles.
The list: House Carne Diem wine plus Panzano-vintner bottles available to BYO or to buy from the shop downstairs
Tip: One dinner seating only at 20:00 in Panzano; book months in advance through the official site.
Founded 1872 as chocolatier to the House of Savoy. Outdoor terrace gives the best dusk view on Piazza della Signoria, now hosting evening wine and savoury pairings.
The list: Glass-pour list expanded since 2023 with Italian regional bottles paired to savoury plates
Tip: Daytime tourists clear after 21:00; come for a late Negroni and the view of the lit-up Loggia dei Lanzi.