Romantic Weekend
Tour Data
A luxury long weekend that will give you a chance to experience the Tuscan countryside, cover some highly entertaining roads, enjoy some great food in incredible locations and sample the car you have always wanted
| Run as either a 3 Night or 4 Night trip (Friday, Saturday, Sunday & Monday or the 4 night version) | |
| Max km allowance 750km (extra KM rates apply if you exceed this limit) | |
| The itinerary is a ‘summer’ season itinerary and can be booked from the start of May through to the end of October | |
| This itinerary is defined as a weekend trip from Friday through to Tuesday morning, but on request we can arrange the trip as a weekday event. | |
| For prices please click on the booking tab above |
Friday – Day 1
Your personal driver meets you at Pisa or Florence airports (other airports available on request) and transports you to our starting base at Lucca where you will be shown around your chosen vehicle, have the route and navigation system explained and any questions answered by the CDT member of staff.
The afternoon drive takes you through the Alpi Pisani and onwards via the Val d’Era to your first stop-off point at Volterra. As with all of our carefully defined routes you will be taken along fairly technical roads with some stunning views and photograph locations. Our detailed roadbook in conjunction with the GPS navigation system will suggest many possible viewpoints, bars of interest and give you notes about the section to be driven. However, you can always choose a different route if you prefer!
From Volterra you will follow the ancient “Strada Volterrana” route towards your booked hotel. The hotel is of course 5 stars and has full Spa facilities. Your reserved Superior Room is yours for two nights so there is no early rush to leave on Saturday morning.
The hotel is in fact a fully restored 15th century villa originally of the family Machiavelli.
Dinner is booked for you in the hotel's exclusive restaurant. Normally we book tables for 8pm but please let our staff know if you would prefer earlier or later dining.
Estimated driving distance today: 150km
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Day 2 - (The "Three night" version of this weekend itinerary omits this day)
Today has the benefit of being a ‘circular’ day as you are returning to the same hotel. The day can be filled with driving, using the hotel Spa facilities, or we can organise one of a number of optional special activities such as a helicopter ride over Chianti, a hot air balloon ride, cooking lessons etc (to enquire about booking these activities please email ClassicDreamTour). Or you may mix and match the above options.
If you want to drive, our roadbook details a couple of possible routes that will take you through the heart of Tuscany and of course give you the chance to stop off at the most interesting locations. From the hotel you are just a few KM south of Florence and so that may also become a destination. If you decide to visit Florence, please follow our GPS directions to our secure parking garage in the centre of this historic city.
Dinner may again be taken at the hotel or we will make a reservation at one of our favourite restaurants in the local area for you. Please let CDT know before lunchtime if you need a reservation making (unless purchasing the on site 'Concierge' service).
Estimated driving distance today: 100-200km
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Day 3
This morning you are heading south through the heart of Chianti. The route takes you along the sinuous SR222 ‘Chiantigiana’ road to Siena before lunch before an easy afternoon over the Monte San Savino and across the Chiana valley.
The morning drive along the 222 takes you along one of the most typical and picturesque areas of Italy. There are a number of small towns worth a quick look such as Panzano, Castellina and Greve. You may stop and purchase bottle of the infamous local wines in any number of “vendita diretta” stalls, not to ignore the olive oil. We suggest a lunch stop is taken in the picturesque village of Palazzuolo at the Trattoria “La Scuderia”, but Sunday lunch reservations are advised so please let CDT know in the morning if you would like a reservation.
Palazzuolo is located on the SS73 which is one of the greatest driving roads (although quite short) in the area, The curves link forest, vineyard and olive grove with some breathtaking views with a good surface and lots of carriage width.
The evening destination is just south of the historic Etruscan town of Cortona where you will be welcomed by our selected hotel.

he hotel is a historic residence dating from 1464, once the hunting manor of Cardinal Passerini who enjoyed position as the bishop of Cortona and the treasurer of the Vatican! We have reserved a suite for your stay and dinner in the hotel’s stylish restaurant. The owners will be more than happy to advise over the choice of wine to compliment your meal.
Estimated driving distance today: 150km
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Day 4
The last full day of driving takes you on a loop of southern Tuscany passing Montepulciano, Pienza, Buonconvento, Massa Marittima and then north back via Pontedera to Lucca. This is the longest drive of the trip.
The morning drive covers the area of southern Tuscany/Northern Umbria with its more gentle, rolling hills before becoming the more typical Tuscan landscape again around Pienza. Pienza is well worth a look with its 15th century (partial) transformation ordered by the then pope, Pius II who was native of this small town
We suggest lunch at the country style Griglieria La Boccia near Massa Marittima (directions are in the roadbook provided). As the name suggests, La Boccia specialises in grilled meats, the "Agnello Scottaditto" (lamb) is a particular favourite.
The final stretch from Massa Marittima up the SR439 is another driver’s delight and is a fine way to round of a motoring trip

The final hotel is the location where your trip started just a few days ago, just a couple km south of Lucca.
Dinner is booked in the hotel’s restaurant.
Estimated driving distance today: 250km
Day 5 - AM
You will be driven back by your private driver to your selected airport.
Whats included
The tour includes the following:
- 3 or 4 Nights of luxury 5 star accommodation (depending on option selected)
- Hire of classic car or modern supercar (unless own vehicle option selected) for entire trip
- 750km of driving allowance
- Chauffeur driven airport transfers
- GPS navigation system with predefined routes
- Bound personalised road book
- 24 hour concierge line
- Personalised reminder of your trip
- Restaurant reservations service
- Any special tickets (depending on itinerary)
- Optional on site 'Personal Assistant' service to arrange refuelling, car washing for each morning, baggage transport and on site support

