2 Week Itinerary in Tuscany
By Gillian Boyd Published 14 August 2026
2 week itinerary in Tuscany, with rolling vineyards, hilltop towns, world-class wine and food, a little history and the drama of the Palio di Siena horse race.
Like many people, we were invited to a wedding in Tuscany, Italy and decided to extend our trip to explore Tuscany.
This guide is based on our experience and the route we took. Rome is also within reach but does not feature on this trip as we had been there before.
As with all our guides, you can pick and mix to create your own plan. Just click on the links for more detail.
Castello di Verrazzano near Florence, Tuscany
Transport
Airports
We flew in and out of Florence airport, but Pisa and Rome are also good alternatives.
Trains
Italy is well served with trains between the major cities. We took trains for the first week from Florence to Lucca, Pisa and Cinque Terre.
More information can be found on the official train website Trenitalia.
The man in seat 61 is a good source of information on trains worldwide.
Hire Car
For the second week, we collected a hire car in Florence (as we were flying back from Florence) and based ourselves in Siena and Montepulciano while we toured around the hill top towns and vineyards. If you are going to small vineyards and a bit off the beaten track, as we did, then hire a car with good clearance such as a small SUV.
Also, remember to check if your accommodation has parking or if there is a public car park nearby as parking can be tricky in high season. Many hilltop towns have carparks on the outskirts.
2 Week Itinerary Summary
Day 1-3: Florence
Day 4: Pisa
Day 5: Lucca
Day 6-7: Cinque Terre
Day 8: Florence and drive SR 222
Day 9-11: Sienna
Day 12-13: Montipulciano
Day 14: Florence and return home
Duomo in Florence
Day 1-3: Florence
Wander the compact beautiful old city of Florence with history and art on every street corner.
Climb the Dome and Giotto’s Bell Tower for views, visit the Uffuzzi Galleries, Ponte Vecchio, Basilica of Santa Maria Novella, Piazza della Signoria and Fountains of Neptune and see the statue of David before you eat a Bistecca Florentine.
Learn about the famous (infamous) Medici family and other notables from Florence.
Or just 45 mins away, you could take a Pasta Cooking Class and Wine Tasting on an Organic Farm as we did.
Leaning Tower of Pisa
Day 4: Pisa
It’s easy to see the iconic Leaning Tower of Pisa, Cathedral, Baptistery and Monumental Cemetery in a day and still have time to take some fun optical illusion photos. You could travel by train from Florence or Lucca.
If you arrive in Pisa on a morning flight you could see the Leaning Tower in the afternoon.
The Piazza dell’Anfiteatro in Lucca, Tuscany
Day 5: Lucca
Lucca is a quaint walled city full of history and a free annual historical re-enactment day through the centuries, with battles, guns fired, costumes, drums and dancing – not to be missed!
Pay homage to its Roman roots while you sip a drink or have a meal in the former Roman amphitheatre, now the main square, the Piazza dell’Anfiteatro.
Climb the Torre Guigini, a tower with oak trees growing at the top for views of Lucca and its surrounding mountains.
We loved Lucca and would recommend at least 1 more day if you have the time to spare.
Riomaggiore in Cinque Terre on the Italian Riviera
Day 6-7: Cinque Terre
Explore the 5 breathtaking colourful UNESCO listed villages on the Italian Riviera, linked by trains and hiking routes that take you past vineyards clinging to the hillside.
You could easily spend longer in Cinque Terre if you wanted. Monterosso al Mare even has a traditional wide sandy beach with umbrellas and sun loungers while the others have harbour dips.
Each village has its own character but all are colourful with cute shops and restaurants. It’s busy so book ahead.
Panzano hilltop town surrounded by cypress trees in Tuscany
Day 8: Florence and drive Via Chianti SR222
Collect a hire car in Florence and take your time driving south on the scenic Via Chiantigiana, SR222, with its rolling hills and landscapes. So beautiful it is also a popular cycle route.
It would take only an hour or two to drive, but you pass through pretty hill top towns such as, Greve in Chianti, Panzano in Chianti and Castellina in Chianti on your way to Siena that are worth exploring.
Maybe stop off at some vineyards along the way too. It’s your time and your schedule. The toll road is faster but not as pretty.
Siena Cathedral and Tower
Day 9-11: Siena
Explore the old walled city and Cathedral, the Palazzo Pubblico and the seashell-shaped Piazza del Campo at leisure. There are plenty of bars, restaurants and shops in Siena.
Try and time your stay for the centuries old bareback horse race and historical procession, the Palio di Siena on 2 July and 16 August each year (weather permitting).
Away from Sienna you can visit San Gimignano hilltop town (known as the town with 5 towers) and Castello di Brolio and Fonterutoli vineyards.
If you want something different, visit the natural thermal baths surrounded by lush forest at Bagni San Filippo only 70km away.
Crowd waiting for the Palio di Siena Horserace and Historical Procession
The White Whale limestone formation at Bagni San Filippo Hot Springs
Montepulciano and surrounding countryside in Tuscany
Day 12-13: Montepulciano
Montepulciano is a famous hilltop town and wine region with top class restaurants and boutique shops. Visit the Piazze Grande, climb the Tower and do the Underground City Wine Tour and learn about its history.
From Montepulciano we visited the hilltop towns of Pienza, Montalcino and Monticchiello.
Or just 30 mins away by car is Bagni San Filippo Hot Springs.
Day 14: Florence Airport
Travel back to Florence Airport and return hire car before flying home.
Final Thoughts
Tuscany features on many Italian bucket lists for its rolling landscapes and world class wine and food. Add to the fact it is close to Florence, Pisa and Cinque Terre and you have a great holiday in the making, with lots of variety. The destinations are close enough to each other that you can mix it up which ever way you want, squeeze it all in or spread it out and take it slow. Your trip, your choice.