Tuscany travel itinerary which shows you the best of Tuscany in 5 days long roadtrip. You will soon realize, why Tuscany is such a popular destination.
We are guessing most of you don’t have a month to travel around Tuscany, so we came up with this 5 perfect days in Tuscany itinerary, which shows you all the must places in this romantic Italian region. Rent a car and enjoy the ride.
Best 5 days Tuscany travel itinerary and the best places to visit
Our Tuscany itinerary starts in Florence. If you plan to arrive in Florence before lunch, walk around the city center, which is like an outdoor art gallery. If you are into art, you will probably want to visit some galleries here as well. It is worth it, but make sure, to still have time for your Il Duomo (city’s cathedral) climb, Ponte Vecchio and Piazzele Michelangelo for the sunset.
Find yourself an accommodation in Florence > Florence accommodations.
Day 2 (Florence – San Marcello Pistoiese – Lucca – Pisa) – app. 140 km
Your own transport will be very useful in this Tuscany itinerary, as you will be exploring northern hilly area in Tuscany. Make sure to stop at suspension bridge near San Marcello Pistoiese. The suspension bridge is already a little bit outside of the town, towards Lucchio.
Before reaching Lucca town, you will be driving through small and traditional villages, which are perfect to get to know the easy going local life. Stop for a coffee and enjoy doing nothing. Before reaching Lucca, your Tuscany itinerary will also take you to Ponte Della Madalena (The Devil’s Bridge). According to a legend, the bridge was built by the devil, in exchange for someone’s life. Inventive locals sent a dog first.
According to our Tuscany itinerary you should reach Lucca town in time for your lunch. Walk around this cute old town, which was established by the Etruscans. Rent bikes to drive on the city walls, and tick off your travel bucket list, for driving your bike on a very unique biking path.
Continue your day and your Tuscany itinerary towards Pisa, which you should reach in the afternoon. You probably guessed what you will do there – yes, climbing the leaning tower is a must! The whole area with basilica and baptistery is incredible!
Book your hotel somewhere in Pisa or in the vicinity of it. > Pisa accommodations
Day 3 (Pisa – San Gimignano – Siena) – app. 125 km
After your morning cappuccino continue your way to San Gimignano. This 4 towers medieval town is on a UNESCO heritage protection so a stop on the Tuscany itinerary is an absolute must. Walk around it and enjoy the views, which also Knight Templars once had. Close your walking tour with a delicious gelato on the main square.
Another famous Tuscany town awaits – Siena. Lunch at the famous central square (Piazza del Campo) will be a great start – after all, the square is known as the most beautiful medieval square in Europe! To get the feel for the large square, climb up to 88 meters high church tower. Not only the views down the Siena are spectacular, if the sky is clear, you will also see the famous Tuscany landscape with its hills, which are also on your travel itinerary for Tuscany later on.
Enjoy the rest of your day just walking around, visiting cute shops selling Italian pastas, salamis and souvenirs and make sure to stop at a local café. Instead of coffee, order yourself Aperol Spritz – a very popular thing to drink among Italians.
Book your hotel in Siena and enjoy your nightlife there > Siena accommodations
Day 4 (Siena – Montepulciano – Bagni San Filippo – Castellini in Chianti) – app. 183 km
The Tuscany itinerary finally takes you to the famous Tuscany landscape today. No matter if you travel to Tuscany in the summer, spring, autumn or winter – the landscape will always charm you! To really enjoy the countryside, rent a car for this day and stop wherever you want – it is worth it!
Continue your way to natural spas – Bagni San Filippo, where the old Romans once were regular guests.
After relaxation in the thermal water, you will have enough energy to do the final stop on today’s Tuscany itinerary – the wine region of Chianti. Book a room somewhere around Castellina in Chianti – in the heart of the vineyards > Castellina in Chianti accommodations
Day 5 (Castellina in Chianti – Greve in Chianti – Florence) – app. 50 km
Another day on your Tuscany itinerary where renting a car is the best option. You will definitely want to explore the famous Chianti wine region. Just don’t drink and drive.
You will end your day and with that your 5 days Tuscany itinerary in Florence again. Leave Florence or book another night there to get a feel for some nightlife > Florence accommodations
TRAVEL TIP: If you can stretch with your budget a bit, we recommend you to book at least one night in an Agriturismo (homestead). Mainly agriturismos are somewhere in the countryside, offering AMAZING views over Tuscany hills. If you will be traveling around Tuscany during summer months, you will love the fact, that almost all the agriturismos have their own outdoor pool. Perfect to enjoy your romantic Tuscany travel!
Check agriturismos in Tuscany here.