Tuscany

Is 3 days enough for Tuscany?

Yes, if you pick one base and move little. Covering Florence, Siena, Pisa and the countryside in three days is a trap. You will spend half your time on buses. This plan keeps you in southern Tuscany for two days and lets Florence have one full day. You lose the coast and the wine roads, but you gain real depth in Siena and the Val d'Orcia.

Day 1: Siena and the heart of the city

Morning, Piazza del Campo and the Duomo (08:30 to 12:30)

Start at Piazza del Campo before 09:00. The square is empty and the sun hits the red brick just right. Walk up to the Torre del Mangia (10 EUR, open 10:00 to 19:00). The 400 steps are steep but the view over the entire city is worth it. Then go to the Duomo (8 EUR for the cathedral, 15 EUR for the full pass that includes the Piccolomini Library and the Baptistery). Book the Duomo online the night before to skip the ticket office line. The mosaic floor is uncovered only until late July, so on July 11 2026 you will see it. Spend 45 minutes inside.

Lunch, Simple panini near the Duomo (12:30 to 13:30)

Walk to Via dei Rossi. Antica Pizzicheria Porciatti does a 7 EUR porchetta panino on fresh schiacciata. Eat standing. No seating, no fuss.

Afternoon, The Contrada museums and a walk to San Domenico (14:00 to 17:00)

Siena is divided into 17 neighborhoods called contrade. The Museo della Contrada della Torre (3 EUR) is small but tells you why locals still run horse races. Then walk downhill to the Basilica of San Domenico. It is free. Inside you will see the head of Saint Catherine. That is not a metaphor. It is her actual head in a reliquary. The view from the terrace looks over the whole valley.

Evening, Aperitivo and a trattoria (19:00 onwards)

Go to the bar La Taverna di Cecco on Via Cecco Angiolieri. A glass of Chianti Classico costs 4 EUR. They bring free snacks. For dinner, Trattoria La Torre on Via Salicotto does a 12 EUR pici cacio e pepe that is better than any tourist spot near the square. Book a table for 20:00. The walk from the bar is 5 minutes.

Day 2: San Gimignano and a drive through the Val d'Orcia

Morning, Bus to San Gimignano (08:00 to 12:30)

Take the Siena-Mobilita bus number 130 from Piazza Gramsci. Buy a round-trip ticket for 12 EUR at the tobacco shop inside the bus station. The bus leaves at 08:15 and arrives at 09:15. San Gimignano is crowded by 11:00, so you get there early. Walk up to the Rocca fortress for the free view. Skip the climb of the Torre Grossa (9 EUR) if you already did the Mangia. Instead, walk the perimeter walls. The best gelato in town is at Gelateria Dondoli near Piazza della Cisterna. A medium cup costs 4.50 EUR. Get the crema di Gorgonzola e noci if you like salt, or the classic saffron. Do not be nice to the street sellers offering free bracelets. They will demand money.

Lunch, packed or quick (12:30 to 13:15)

Grab a 5 EUR pizza at Il Tirolese near the bus stop. The bus back to Siena leaves every hour, last one at 19:00.

Afternoon, Val d'Orcia by rental car (14:00 to 19:00)

This is the only part where you need a car. Rent one from Siena train station (Hertz, about 55 EUR for 24 hours). Book it online 48 hours ahead, otherwise they run out. Drive south on the SS2 (Via Cassia). Stop at Pienza (25 km, 30 minutes). Park outside the walls. Walk through the main street to the panoramic terrace behind the church. It looks exactly like the postcards. Then drive 10 km to Montepulciano. Walk up Via di San Donato to Piazza Grande. The wine cellars underneath the square are free to enter. Buy a bottle of Vino Nobile for 15 EUR. Drive back to Siena by 19:00 to avoid night driving on the curvy roads.

Evening, Dinner in Siena (20:00)

Osteria Il Gatto on Via Pellegrini. The 10 EUR ribollita soup is thick and filling. Locals eat here, not tourists.

Day 3: Florence in a day

Morning, Train and early art (07:00 to 13:00)

Take the regional train from Siena to Florence Santa Maria Novella. Buy the ticket at the station for 16 EUR. The ride takes 1 hour 25 minutes. Arrive by 08:30. Walk straight to the Accademia Gallery (17 EUR). Pre-book the 09:00 slot three weeks in advance. It sells out. You see David. 15 minutes inside is enough. Then walk to the Duomo complex. Skip the climb (the queue is 45 minutes and the view is worse than Siena). Instead, go to the Baptistery (free with the Duomo pass, but buy only the Duomo pass for 20 EUR if you want the museum and baptistery). Actually, buy the 15 EUR Brunelleschi Pass online. It includes the Baptistery, the Opera del Duomo museum and the crypt. The museum has the original doors. The line for the Baptistery is 5 minutes.

Lunch, The Central Market (13:00 to 14:00)

Mercato Centrale on the ground floor. Mario at Da Nerbone does a 7 EUR lampredotto sandwich. The queue moves fast. Eat at the counter.

Afternoon, Oltrarno and a real workshop (14:00 to 17:00)

Cross the Ponte Vecchio at 14:30. Do not stop on the bridge, keep walking to Via Maggio. Then go to Santo Spirito square. The church is free and has a Brunelleschi design. A 10 minute walk from there takes you to the Scuola del Cuoio (Via San Giuseppe 5R). It is a leather school inside Santa Croce. You can watch artisans stamp leather. No entry fee. Buy a belt for 40 EUR directly from the maker, not from a shop next door. Skip the Uffizi gallery. You do not have time to do it justice in one day.

Evening, Final dinner and train back (18:00 onwards)

Take the 19:30 train to Siena (or to Rome if you are flying out). Before that, eat at Trattoria Cammillo on Borgo San Jacopo. A 14 EUR spaghetti alle vongole. Cash only. They do not take cards.

Where to stay for this itinerary

Siena, Historic center (Antiporto area or Piazza del Campo side) Reason: You spend two nights here and walk everywhere. The bus to San Gimignano leaves from Piazza Gramsci, which is a 10 minute walk from the center. Price: 120 to 160 EUR per night for a double in August 2026.

Florence, Santa Maria Novella (near the train station) Reason: Only if you skip Siena entirely and do this itinerary in reverse. Not recommended. But if you must, this area saves you 15 minutes walking each morning. Price: 180 to 220 EUR per night in July 2026.

Val d'Orcia, agriturismo near Pienza Reason: If you rent a car for all three days and do not want to stay in town. You trade convenience for silence and views. Price: 100 to 150 EUR per night, but you need breakfast included since the nearest bar might be 3 km away.

Practical tips

• Book the Accademia gallery for Florence 3 weeks ahead. The official website is B-Ticket. The 17 EUR ticket includes the temporary exhibits.
• In Siena, the walk from the train station to the historic center is uphill. 15 minutes of stairs. A taxi costs 12 EUR. Not worth it unless you have heavy bags.
• The bus from Siena to San Gimignano can be full by 08:00 on Saturdays. Arrive by 07:50 to get a seat.
• No need to buy a tourist pass for Tuscany. Individual tickets cost less than a pass for the places you will actually visit.
• Avoid eating on Piazza della Signoria in Florence. A 14 EUR pasta there becomes 22 EUR. Walk two streets away.

FAQ

Can I do Pisa instead of San Gimignano on day 2? Yes, but I do not recommend it. Pisa is 30 minutes by train from Florence, but from Siena it is 2 hours or a 90 minute drive. The leaning tower is a 20 minute photo. You lose the hill town and the countryside. San Gimignano gives you more of Tuscany in less time.

Do I need a car? Only for day 2 afternoon in the Val d'Orcia. If you skip that part, you can do all three days by bus and train. But the Val d'Orcia is worth the rental.

What if my flight arrives in Rome? Take the Frecciarossa from Rome Termini to Florence (1 hour 30 minutes, 40 EUR), then a train to Siena (1 hour 30 minutes, 16 EUR). Or rent a car in Rome and drive to Siena in 2.5 hours on the A1. The key is to avoid the Rome to Siena bus (3.5 hours, unreliable).

Is August too crowded? Yes, especially Florence. Siena gets full but it is manageable if you start early. The Palio horse race is on August 16 2026. Prices double. Avoid that weekend.

How much money do I need for three days? About 350 EUR per person for food, transport, entry fees and a basic double room split between two people. Add 55 EUR for the rental car if you drive. Add 20 EUR per gelato you did not plan to buy.