Florence and Tuscany itinerary, day by day

From Florence through the Chianti hills to Siena and San Gimignano, in the cradle of the Renaissance: the map, what is worth booking and everything that costs nothing.

🗓️ 4 or 7 days📍 3 stops☀️ Best time: May to June and September to October

Florence · Photo Titouan Jullien / Pexels

Route map (numbers = order of the stops).

Florence and Tuscany in 4 days

2 stops · 8 things to do · ≈ 60 km

1Florence

Days 1-2

The capital of the Renaissance, where the Duomo, the Uffizi and the Ponte Vecchio are all a few minutes' walk from one another.

🎟️ Worth booking

Uffizi Gallery, skip the line2h30 · from €30
Botticelli, Leonardo, Michelangelo, Raphael: one of the great art collections of the world, and a queue well worth skipping.
Book on GetYourGuide →
Climbing Brunelleschi's dome1h · from €20
463 steps between the two shells of the dome, past the frescoes of the Last Judgement, to the view from the lantern. Entry is by timed slot.
Book on GetYourGuide →

✦ Free, not to be missed

Ponte Vecchio · Piazzale Michelangelo at sunset · The Oltrarno

🛏️ Where to sleep · Budget: Plus Florence (€42 a night) · Mid-range: Hotel Davanzati (€145 a night) · Luxury: Four Seasons Hotel Firenze (€800 a night)

🍴 Where to eat · top rated

La tenda rossa ★ 4.9 · 2746 reviews
I' Girone De' Ghiotti ★ 4.8 · 5015 reviews · €
Osteria Vecchio Cancello ★ 4.8 · 2584 reviews · €€
Restaurant Il Vezzo ★ 4.8 · 1604 reviews · €€
Osteria del Corso ★ 4.8 · 1307 reviews

Photo Pexels

🚗 Car · 45 min · 40 km

2The Chianti hills

Days 3-4

Vineyards, cypresses and hilltop villages between Florence and Siena: the heart of Tuscan wine.

🎟️ Worth booking

Tasting at a Chianti estate2h · from €35
The cellars, then a tasting of Chianti Classico, the wine with the black rooster on the neck of the bottle.
Book on GetYourGuide →

✦ Free, not to be missed

The Chiantigiana road (SR222) · Greve in Chianti

🛏️ Where to sleep · Budget: Hotel Palazzo Squarcialupi (€100 a night) · Mid-range: Albergo del Chianti (€130 a night) · Luxury: Castello di Spaltenna (€290 a night)

🍴 Where to eat · top rated

La tenda rossa ★ 4.9 · 2746 reviews
Ristorante Steakhouse EZIO ★ 4.9 · 300 reviews
Osteria Vecchio Cancello ★ 4.8 · 2584 reviews · €€
Ristoro di Lamole ★ 4.8 · 2119 reviews · €€
La Castellana ★ 4.8 · 1350 reviews · €€

Photo Anna.Massini / CC BY-SA 4.0 (Wikimedia Commons)

Florence and Tuscany in 7 days

3 stops · 11 things to do · ≈ 150 km

1Florence

Days 1-3

The capital of the Renaissance, where the Duomo, the Uffizi and the Ponte Vecchio are all a few minutes' walk from one another.

🎟️ Worth booking

Uffizi Gallery, skip the line2h30 · from €30
Botticelli, Leonardo, Michelangelo, Raphael: one of the great art collections of the world, and a queue well worth skipping.
Book on GetYourGuide →
Climbing Brunelleschi's dome1h · from €20
463 steps between the two shells of the dome, past the frescoes of the Last Judgement, to the view from the lantern. Entry is by timed slot.
Book on GetYourGuide →

✦ Free, not to be missed

Ponte Vecchio · Piazzale Michelangelo at sunset · The Oltrarno

🛏️ Where to sleep · Budget: Plus Florence (€42 a night) · Mid-range: Hotel Davanzati (€145 a night) · Luxury: Four Seasons Hotel Firenze (€800 a night)

🍴 Where to eat · top rated

Photo Pexels

🚗 Car · 45 min · 40 km

2The Chianti hills

Day 4

Vineyards, cypresses and hilltop villages between Florence and Siena: the heart of Tuscan wine.

🎟️ Worth booking

Tasting at a Chianti estate2h · from €35
The cellars, then a tasting of Chianti Classico, the wine with the black rooster on the neck of the bottle.
Book on GetYourGuide →

✦ Free, not to be missed

The Chiantigiana road (SR222) · Greve in Chianti

🛏️ Where to sleep · Budget: Hotel Palazzo Squarcialupi (€100 a night) · Mid-range: Albergo del Chianti (€130 a night) · Luxury: Castello di Spaltenna (€290 a night)

🍴 Where to eat · top rated

Photo Anna.Massini / CC BY-SA 4.0 (Wikimedia Commons)

🚗 Car · 1h10 · 70 km

3Siena and San Gimignano

Days 5-6

Florence's old Gothic rival, built around its shell-shaped square, and nearby the hill town that still keeps its medieval towers.

🎟️ Worth booking

Guided walk through Siena2h · from €25
Piazza del Campo, the striped cathedral, and the medieval lanes of the contrade, the seventeen districts whose horses race in the Palio.
Book on GetYourGuide →

✦ Free, not to be missed

Piazza del Campo · San Gimignano

🛏️ Where to sleep · Budget: Hotel Alma Domus (€80 a night) · Mid-range: Hotel Athena (€130 a night) · Luxury: Castel Monastero (€300 a night)

🍴 Where to eat · top rated

Ristorante Fuoriluogo ★ 4.8 · 1368 reviews · €€
Osteria La Sosta di Violante - La corte di San Giorgio ★ 4.7 · 2916 reviews · €€
Il Ceppo Toscano ★ 4.7 · 1477 reviews · €€€
Ristorante La Locanda dei Tintori Siena ★ 4.7 · 1127 reviews · €€
Cum Quibus - Ristorante Toscano ★ 4.7 · 541 reviews · €€€€

Photo Pexels

Hotel prices are per room per night, activity prices per person, checked when written. Some links are affiliate links (Booking, GetYourGuide): we may earn a commission, at no extra cost to you.

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The free printable Florence and Tuscany guide: map, stops day by day, hotels by budget. Works offline.

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Good to know before you go

🍽️ What to eat

Bistecca alla fiorentina: a thick T-bone steak, grilled over coals, served rare and priced by weight.
Ribollita: bread and bean soup with black cabbage, better on the second day, as the name suggests.
Pici: thick pasta rolled by hand around Siena, often served all'aglione, with garlic and tomato.
Panforte and cantucci: Siena's dense cake of nuts and candied fruit, and almond biscuits dipped in vin santo.
Lampredotto: tripe in a bread roll from a Florentine street cart, for the curious.
Chianti Classico: the red of the hills between Florence and Siena, made mostly from Sangiovese.

⚠️ What to avoid

Restaurants with photo menus and someone outside waving you in, above all near the Duomo.
Check the bill for coperto (the cover charge) and service before you add anything.
Do not drive into central Florence or Siena: cameras fine every car without a permit.
Shoulders and knees covered in churches, the Duomo included.
In summer, book the Uffizi and the dome climb weeks ahead.

Plan this trip

📒 The free printable Florence and Tuscany guide→ 🗓️ Best time to visit Florence and Tuscany, month by month→ 🎟️ What to book before you go→

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