Morning
Land at Florence (FLR)
Amerigo Vespucci sits about 15 minutes from the centre and the T2 tram runs into town. Pisa is the cheaper alternative, an hour away by train.
Check in: Palazzo Guadagni
Piazza Santo Spirito 9, in Oltrarno. A Renaissance palazzo on the square, with the Loggia roof bar on the third floor.
Afternoon / Day
Lunch at Procacci
Via de' Tornabuoni 64r. Trading since 1885 and still selling truffle panini and a glass of Antinori at the marble counter. Closed Sundays.
Basilica di Santa Croce
Piazza Santa Croce 16. Michelangelo is buried here; the Dante monument is an empty cenotaph, because Ravenna never gave the body back.
Affogato at Vivoli
Via Isola delle Stinche 7r, a lane behind Santa Croce. Family-run since 1929 and now in the fourth generation — order the gran crema al caffè affogato, not a cone.
Evening
Dinner at Buca Lapi
Via del Trebbio 1r, in the cellars of Palazzo Antinori. Open since 1880 and the oldest restaurant in Florence — this is the bistecca night. Book.
The Duomo after dark
Piazza del Duomo. Walk the floodlit square once the queues and the tour flags have gone; it is a ten-minute stroll back over the river.
Morning
Galleria dell'Accademia
Via Ricasoli 58. Michelangelo's David at the end of the hall of unfinished Prisoners. Timed entry, closed Mondays — take the first slot of the day.
Piazza della Signoria
The Loggia dei Lanzi is an open-air sculpture hall that costs nothing: Cellini's Perseus, Giambologna's Sabine, and a copy of David at the door.
Afternoon / Day
Lunch at Mercato Centrale
Piazza del Mercato Centrale. The food hall fills the first floor of the historic San Lorenzo covered market — separate counters for pasta, tripe and wine.
Uffizi Gallery
Piazzale degli Uffizi 6. Book an afternoon slot: the gallery runs Tuesday to Sunday, 8:15 to 18:30, and shuts on Mondays. Allow three hours.
Ponte Vecchio
The goldsmiths' bridge, and the only Florentine bridge left standing in 1944. Vasari's corridor runs above the shops on the upstream side.
Evening
Aperitivo at Le Volpi e l'Uva
Piazza dei Rossi 1, a small square just past the Ponte Vecchio. A counter enoteca — ask what the small growers have open by the glass.
Evening at the Loggia Roof Bar
Palazzo Guadagni, third floor. The hotel's own panoramic terrace runs to lunch, tea and aperitivo — ask what the kitchen has on before you plan the whole evening round it.
Morning
Climb Brunelleschi's Dome
Piazza del Duomo. Reserve the timed climb well before you fly. The state museums close on Mondays; the cathedral complex does not, so today is the day.
Battistero di San Giovanni
Piazza San Giovanni. The whole ceiling is a gold Last Judgment mosaic. The Gates of Paradise on the square are copies; the originals sit in the museum.
Afternoon / Day
Lunch at S.Forno
Via di Santa Monaca 3r. The Santo Bevitore group's bakery in Oltrarno — bread, focaccia and a short counter menu between the Duomo and Boboli.
Boboli Gardens
Piazza de' Pitti 1. Palazzo Pitti is shut on Mondays but the garden behind it is open — except on the first and last Monday of each month.
Basilica di Santo Spirito
Piazza Santo Spirito. Brunelleschi's last church closes the square the hotel stands on; the bare front was never given its facade.
Evening
Gregorian vespers at San Miniato
Via delle Porte Sante 34. The monks sing vespers in Latin and Gregorian chant every afternoon at 18:30. Entry is free and nothing is booked.
Sunset at Piazzale Michelangelo
Walk down from San Miniato as the light goes — the terrace is five minutes below the basilica and you arrive from above the crowd.
Dinner at Il Santo Bevitore
Via di Santo Spirito 64. Oltrarno's long-running dining room, ten minutes downhill from the piazzale and two from the hotel. Reserve.
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Morning
Pick up the rental car
Florence's centre is a camera-enforced ZTL, so collect near Santa Maria Novella station and drive straight out on the SR222. Settle who drives first.
Antinori nel Chianti Classico
Via Cassia per Siena 133, Bargino. Book the cellar visit ahead; the estate is about 25 minutes south of Florence, just off the Siena superstrada.
Afternoon / Day
Lunch at the Falorni bistro, Greve
Piazza Giacomo Matteotti 66. A butcher since 1806, nine generations in. The butcher counter closes Wednesdays and Sundays, so time the visit.
Castello di Verrazzano
Via Castello di Verrazzano 1, Greti. Open 10:00 to 18:00 daily — book the guided cellar tour rather than turning up for the shop.
Drive on to San Gimignano
SR222 down to Poggibonsi, then up the hill — about an hour. Park in the lots outside the walls; the old town takes no cars.
Evening
Collegiata di Santa Maria Assunta
Piazza del Duomo. Open to 19:30 Monday to Friday from April to October, so a late arrival still works. The Palazzo Comunale next door sells the Torre Grossa climb.
Gelato at Dondoli
Piazza della Cisterna 4. Sergio Dondoli works saffron and local herbs into the list alongside the classics; the queue thins once the coaches go.
Check in: Palazzo Ravizza, Siena
Pian dei Mantellini 34, 45 minutes on. One of the very few hotels inside Siena's walls with its own parking, which matters in a ZTL city.
Morning
Piazza del Campo
The shell-shaped square tips down to a single point at the Palazzo Pubblico. The Palio is run round the perimeter twice a year, on 2 July and 16 August.
Museo Civico, Palazzo Pubblico
Piazza del Campo 1. Lorenzetti's Allegory of Good and Bad Government fills one room; the Torre del Mangia climb is a separate ticket.
Afternoon / Day
Lunch at Enoteca I Terzi
Via dei Termini 7. Brick vaults built around a 12th-century tower. Lunch runs 12:30 to 14:30 and the place is closed on Sundays.
Duomo di Siena and the Gate of Heaven
Piazza Duomo 8. The Porta del Cielo roof walk is a separate timed ticket; check the site for the weeks when the inlaid marble floor is uncovered.
Santa Maria della Scala
Piazza Duomo 1. A pilgrim hospital for eight centuries; the Pellegrinaio ward is frescoed with its own daily work, and the original Fonte Gaia panels are inside.
Evening
Passeggiata on Via di Città
The curving spine of the old town between the Campo and the Duomo. Contrada flags and fountains tell you whose quarter you have walked into.
Dinner at Taverna di San Giuseppe
Via Giovanni Duprè 132, 300 m from the Campo. Tuscan cooking above an Etruscan cellar cut into the tufa, with around 600 labels. Reserve.
Morning
Drive south to Montalcino
The SS2 Cassia through Buonconvento, about 45 minutes. September is the vendemmia — ask whether the cellar is mid-harvest when you book, and go early.
Abbazia di Sant'Antimo
Località Castelnuovo dell'Abate, below Montalcino. A Romanesque abbey in pale travertine standing alone in an olive valley, still a Benedictine house.
Cellar tour at Fattoria dei Barbi
Località Podernovi 170, off the Castelnuovo dell'Abate road. Historic Brunello cellars, a Brunello museum and a working dairy on one estate. Book ahead.
Afternoon / Day
Lunch at Taverna dei Barbi
Same estate as the cellars, so nobody drives between the tasting and the table. The kitchen cooks the farm's own meat and its own pecorino.
Palazzo Piccolomini, Pienza
Piazza Pio II. Pope Pius II's own palace, with a hanging garden and a loggia looking straight down the Val d'Orcia. Book online before you arrive.
Pecorino tasting at Caseificio Cugusi
Via della Boccia 8, on the Pienza-to-Montepulciano road. A Sardinian family making pecorino di Pienza; they run tastings and farm picnics.
Evening
Cantine Contucci, Montepulciano
Via del Teatro 1, off Piazza Grande. Thirteenth-century cellars under the family palazzo; the cellar visit is free and the Vino Nobile is poured after.
Nightcap in the Ravizza garden
An hour back to Siena on the Bettolle superstrada. After a farm lunch and a cheese board, open the Contucci bottle in the hotel's walled garden.
The Chiantigiana Back to Florence
Morning
Breakfast in the garden
Pian dei Mantellini 34. Eat outside before you load the car; the Ravizza garden looks out over the Sienese hills below the walls.
North on the SR222 Chiantigiana
The slow way back: two lanes through Castellina, Panzano and Greve rather than the superstrada. Allow two hours with stops.
Castellina in Chianti
Via delle Volte, a covered medieval walkway running inside the town wall, with openings out over the vineyards. Twenty minutes and free.
Afternoon / Day
Lunch at Cecchini, Panzano
Via XX Luglio 11. Dario Cecchini's eighth-generation butcher shop and its nose-to-tail grill rooms — book Officina or Solociccia, or eat off the panini truck.
Drop the car at Florence airport
About an hour from Panzano. Returning at FLR keeps you clear of the city ZTL on the one day you cannot afford a fine in the post.
Evening
Fly out of FLR
Amerigo Vespucci is small and quick to clear — but check whether your connection actually leaves from Pisa, an hour west.
