The Tuscany & Porto Ercole five day driving tour is a drive through wine regions of Tuscany, with stops in some of the most luxurious hotels in the whole Europe. You will arrive in Florence to the stunning Villa Cora, located on the hills outside the historical centre of Florence.

On your first drive you will be passing through famous Tuscan movie landscapes in the Montepulciano region, south to Porto Ercole on the coast. This is the location for the five star Hotel Il Pellicano. When many people think of Tuscany they think of the landscapes between Florence and Siena with cypress lined roads, countryside green hills, and vineyards. The coast should not be forgotten – Tuscany has a stunning coastline. Il Pellicano stands on one of the most breathtaking locations.

After enjoying a view over the Mediterranean for a night you will continue the drive the next day, briefly stopping by Bolgheri, where you can visit local vineyards and get to know the producers. The last drives offers even even more picture perfect landscapes – and fantastic driving roads as well. Visit towns like Volterra, Greve in Chianti, San Gimignano, and more.

This is a scenic driving tour with as much focus on the journey as the destinations. Tuscany is a picturesque region to drive in, and if you drive a supercar or classic car you will enjoy the roads even more. But each stop is an opportunity to discover this charming region of Italy – and eat one more gelato.

Day 1Day 2Day 3Day 4Day 5
Tuscany & Porto Ercole - Day 1
Arrive in Florence, check in from 14:00, and spend an evening at leisure exploring the city

Hotel: 5* Villa Cora, Florence – 24 m² deluxe double room with breakfast

Tuscany & Porto Ercole - Day 2
Your car will be delivered to the hotel after breakfast and we will do a short car and tour briefing before you start the first drive. This will take you south from Florence to the Montepulciano, from where the drive continues towards the coast. Arrive in Porto Ercole and check in to a hotel with the most astonishing sea view in the whole Tuscany – the luxurious Il Pellicano with an old authentic Tuscan charm.

Hotel: 5* Hotel Il Pellicano, Porto Ercole – 35 m² sea view double room with breakfast
Distance: 260 km / 4 hours without stops

Tuscany & Porto Ercole - Day 3
After breakfast start your drive to Castello di Casole, one of the most beautiful hotels in the whole Tuscany. To get there you will drive a scenic route that also includes a stop in Bolgheri for lunch, where you will have the opportunity to stop at several local vineyards. Then the drive passes by Volterra, with some very enjoyable driving roads around it. Every time we go to Tuscany we fall in love even more with the roads, the scenery, and the people. Now it is your turn!

Overnight hotel: 5* Castello di Casole – 37 m² studio suite with breakfast
Distance: 220 km / 3½ hours

Tuscany & Porto Ercole - Day 4
For your final drive we have prepared a nice route through the Chianti regions of Tuscany. First stop is in San Gimignano, where we suggest you park the car and take a walk in this charming Tuscan town. From there the drive continues to Via Chiantigiana, the famous “Chianti route”, that takes you back to Florence through some picture perfect landscapes and towns. Spend your last evening at leisure exploring Florence city.

Hotel: 5* Villa Cora, Florence – 24 m² deluxe double room with breakfast
Distance: 200 km / 4½ hours without stops

Tuscany & Porto Ercole - Day 5
Check out by 12:00, or if you wish you can extend your stay in Florence

Tour price calculator
Select the car you want to tour in and fill out the form to submit it to us to receive a non-binding offer. We will check availability for the car and hotels on your requested dates, and answer you by email. Displayed is a base price and prices can increase during high season and public holidays.

Included in tour price:
3 days car rental with insurance (700 km included)
4 nights accommodation for two, including breakfast
Programmed GPS with daily routes, roadbook & map
Personal meet & tour + car briefing with a member of our team
Support by phone & email

Tour price from €0
Our prices include VAT
Cars marked with MT have manual (stick shift) transmission.
5 days / 4 nights
3 days / 680 km
Tour start:
Price from: