The Tuscany & Porto Ercole driving holiday is a journey of discovery through the famous wine regions of Tuscany. The hotels are hand-picked by us to only include the very best ones in Italy. You will be staying in four different exquisite hotels, all places where you can indulge in luxury – and relax.

On your day of arrival to Florence you will check in to the stunning Villa La Massa, the exquisite jewel of the Villa d’Este Group. This 16th Century estate sits on the banks of the Arno River and is surrounded by 22 acres full of lemon trees and olive groves.

The next morning after your breakfast the car of your dreams will await you outside the hotel. On your first drive you will be heading towards famous Tuscan postcard landscapes into the Montepulciano region, and follow sweeping country roads to Porto Ercole, a charming seaside town on the Tuscan coast. Here you will check in to the unique five star paradise Il Pellicano, with a breathtaking private beach. When many people think of Tuscany they think of cypress lined roads, countryside green hills, and vineyard landscapes. You will see plenty of that within the itinerary. However the Mediterranean should not be forgotten – Tuscany has an absolutely stunning coastline, and Il Pellicano stands on one of the most breathtaking seafront locations.

Wake up to the view of a glistening sea and enjoy a sumptuous breakfast on the hotel’s terrace that overlooks the Mediterranean. Today’s drive takes you back inland briefly stopping by the village of Bolgheri, a place where you can visit well-known vineyards and discover the local producers. Your final destination for today is Castello di Casole in Casole d’Elsa, an historic castle now boutique hotel considered to be among the best in the world, surrounded by rolling hills and dreamy views. Enjoy this wonderful destination and relax, because tomorrow’s drive has more surprises in store for you. For your last drive we have lined up even more picture perfect landscapes – and fantastic driving roads as well, as you will follow the most famous wine route Cia Chiantigiana back to Florence. En route you have the chance to visit some of the most beautiful hilltop villages in Tuscany – Volterra and San Gimignano. Upon arrival back in Florence you will check in to an aristocratic residence located inside a centuries-old park that overlooks the Boboli Gardens – the elegant Villa Cora.

Our Tuscany & Porto Ercole supercar driving holiday is a scenic driving tour with as much focus on the picture perfect journey as the luxurious hotel destinations. Tuscany is the most picturesque region to explore, and if you are behind the wheel of a supercar or classic car you will appreciate the scenic driving roads we have chosen for you. Each stop in your itinerary 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 and check in to Villa La Massa from 14:00, and spend an evening at leisure

Hotel: 5* Villa La Massa, Florence – 43 m² prestige 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
Driving time: 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
Driving time: 3½ hours without stops

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
Driving time: 4½ hours without stops

Tuscany & Porto Ercole - Day 5
Check out from Villa Cora is at 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 bespoke tour quotation. We will check availability for the car and hotels on your requested dates, and reply to you by email or phone.

Included in tour price:
3 days car rental with insurance (680 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
Full 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
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