Best driving tours of Italy Classic Vintage Cars Driving Experience

Classic Car Tours in Tuscany

Discover the Dolce Vita on Tuscany’s Most Scenic Roads

Take the wheel of a classic Italian convertible and discover Tuscany at a different pace, following scenic country roads through vineyards, medieval villages and landscapes that seem made for open-top driving.

TuscanTeam’s Classic Car Tours in Tuscany are private driving experiences created for travellers who want to enjoy not only the destinations, but the journey itself. Behind the wheel of a vintage Italian car, even the road between two Tuscan villages becomes part of the experience.

Our itineraries explore some of the most beautiful driving areas in the region. Follow the rolling roads of Chianti, travel through the countryside surrounding Siena, or continue south towards Montalcino, Pienza and Val d’Orcia, where cypress-lined avenues, hilltop villages and panoramic country roads create one of Tuscany’s most iconic landscapes.

More Than a Classic Car Rental

A TuscanTeam driving experience is designed as a complete journey rather than simply a car rental. Each route is carefully planned around enjoyable roads, realistic driving times and selected stops along the way. During scheduled driving days, a TuscanTeam Tour Manager leads the experience in a pilot car, helping with navigation, timing and logistics throughout the journey.

This allows you to concentrate on what matters most: enjoying the car, the road and the freedom of driving through Tuscany.

Depending on the itinerary, the journey can also combine the driving experience with boutique countryside accommodation, wineries, Tuscan lunches and dinners, medieval villages and carefully selected local experiences.

From a One-Day Drive to a Multi-Day Tuscan Journey

For private groups travelling with a minimum of three classic cars, a one-day driving experience can be incorporated into a longer stay in Tuscany. Couples and smaller parties can instead turn the experience into a short countryside escape or make the classic car the centrepiece of a complete multi-day journey. Routes, duration, accommodation and experiences can be tailored around your travel plans and preferred pace.

This is the spirit behind our Dolce Vita Classic Car Tours: beautiful vintage cars, memorable roads and the freedom to experience Tuscany from behind the wheel.

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All about the Classic Car Tours in Tuscany.

Choose Your Classic Car Tour in Tuscany

From a single day behind the wheel to a complete road journey across the Tuscan countryside, TuscanTeam offers different ways to experience Tuscany in a classic Italian car. Each experience combines carefully selected driving routes with the support of our Tour Manager in a pilot car, while our multi-day journeys add handpicked accommodation, food and wine experiences and time to discover the places encountered along the way.

One-Day Classic Car Driving Tour for Private Groups

Designed for private groups travelling with a minimum of three classic cars, our one-day driving tour is the perfect way to add a memorable road experience to a stay in Tuscany. Take the wheel of a classic Italian convertible and follow your TuscanTeam pilot car along panoramic country roads through Chianti, Siena and the surrounding countryside. The route combines enjoyable driving with selected stops, medieval villages and the landscapes that define central Tuscany.

Each classic car accommodates two guests, making the experience particularly suited to groups of friends, families, private celebrations and small incentive groups looking to spend a full day driving together through Tuscany.

Discover our One-Day Classic Car Tour in Tuscany →

3-Day Dolce Vita Classic Car Tour

A short escape designed to turn a classic car experience into a complete Tuscan journey. The 3-Day Dolce Vita Classic Car Tour combines two driving days with two nights in handpicked countryside accommodation, creating the right balance between time behind the wheel and time to enjoy Tuscany.

Drive through scenic wine country and historic villages, with selected food and wine experiences incorporated into the itinerary. It is an ideal option for travellers looking for an immersive driving experience without committing to a longer road journey.

Discover the 3-Day Dolce Vita Classic Car Tour

5-Day Dolce Vita Classic Car Tour

For travellers who want to make classic-car driving one of the highlights of their journey through Tuscany, our 5-Day Dolce Vita Classic Car Tour offers the most complete experience. The itinerary combines three classic-car driving days and four nights in Tuscany, travelling through different landscapes from Chianti and Siena to Montalcino and Val d’Orcia.

Scenic roads are combined with boutique countryside accommodation, wineries, Tuscan cuisine and selected experiences, allowing the journey to develop at a relaxed pace rather than simply driving from one destination to another.

Discover the 5-Day Dolce Vita Classic Car Tour

Private & Custom Classic Car Tours

Not every journey needs to follow a predefined itinerary. TuscanTeam can design private and custom classic car tours in Tuscany around your travel dates, accommodation, group size and the areas you would like to explore. Custom experiences can range from a private driving experience for a group with multiple classic cars to a complete multi-day journey with accommodation, luggage logistics and selected experiences arranged along the route.

This option is particularly suited to families, groups of friends, private celebrations, corporate groups and incentive travel looking for a driving experience created specifically around their plans.

Discover the Art of Classic Car Driving in Tuscany

Curious about what it is really like to explore Tuscany behind the wheel of a vintage Italian convertible? Discover the best driving areas, what to expect from a classic car and the difference between a simple rental and a professionally planned driving experience.

Read our guide to Driving a Classic Car in Tuscany →

The tour package inclusions and exclusions at a glance

What is included in this tour?Items that are included in the cost of tour price.

What’s Included in a TuscanTeam Classic Car Tour

Depending on the selected itinerary, our Classic Car Tours in Tuscany combine the driving experience with professional on-road support, carefully planned routes and selected travel services.

Exact inclusions vary between our one-day, multi-day and custom experiences and are clearly detailed in each individual tour.

Classic Car & Driving Support

✔ Classic Italian convertible for scheduled driving days
✔ TuscanTeam Tour Manager leading the experience in a pilot car
✔ Carefully planned scenic driving routes
✔ Route planning and driving-day coordination
✔ Fuel for the scheduled itinerary
✔ Dedicated mechanical support vehicle for larger group tours, when required

Travel & Logistics

Available according to the selected tour:

✔ Private arrival and departure transfers
✔ Luggage transportation between accommodations when required
✔ Parking and road tolls where specified
✔ On-trip logistical assistance

Accommodation

Included in selected multi-day packages:

✔ Handpicked boutique wine resorts, country hotels or historic countryside properties
✔ Accommodation strategically selected according to the driving itinerary
✔ Double room accommodation for the number of nights specified in the selected package
✔ Daily breakfast
✔ Private bathroom
✔ On-site or conveniently located parking for the classic cars
✔ Accommodation logistics coordinated with the scheduled driving routes
✔ Luggage transportation between different properties, when required by the itinerary
✔ All applicable accommodation taxes, except local city tax where payable directly at the property

Food, Wine & Tuscan Experiences

Depending on the itinerary:

✔ Selected winery visits and wine tastings
✔ Tuscan lunches and dinners where specified
✔ Visits to medieval villages and wine regions
✔ Selected cultural, gastronomic and local experiences

Private & Custom Experiences

For custom journeys, the combination of classic cars, driving routes, accommodation, transfers and experiences is designed around your group, travel dates and preferred style of journey. A detailed list of confirmed inclusions is always provided with your individual itinerary and travel proposal.

Important Driving Information

All classic cars are provided with the insurance coverage required for the rental. However, each vehicle is subject to an insurance excess (damage liability) that must be guaranteed by the driver. Depending on the selected classic car, the insurance excess generally ranges from €1,500 to €5,000 per vehicle.

The applicable excess and rental conditions are confirmed before booking and may vary according to the specific vehicle selected.

Accommodation

Accommodation

Accommodation and location play an important role in the logistics of our Classic Car Tours in Tuscany. The approach differs between our one-day private group experiences and our multi-day Dolce Vita journeys.

One-Day Private Group Tours

For our one-day private classic car tours, the cars can be delivered directly to your hotel, villa or countryside accommodation, subject to location, road access and operational feasibility. Our team coordinates the delivery and collection of the classic cars, allowing your group to start and finish the driving experience directly from your accommodation whenever possible.

If direct delivery is not suitable, we arrange a convenient meeting point positioned along the planned driving route.

Dolce Vita Multi-Day Tours

For our 3-Day and 5-Day Dolce Vita Classic Car Tours, accommodation is an integral part of the journey. TuscanTeam works with a carefully selected collection of boutique wine resorts, country hotels and historic countryside properties located across the areas explored during the tour.

Properties are selected not only for their atmosphere, character and quality, but also for their strategic position along the driving itinerary. This allows us to reduce unnecessary transfers and position each overnight stay close to the scenic roads, villages, wineries and experiences planned for the following driving day.

Depending on the itinerary, the journey can combine stays in the Chianti and Siena countryside, Montalcino and Val d’Orcia, allowing the landscape and character of Tuscany to change naturally as the tour progresses.

The accommodation therefore becomes part of the Dolce Vita journey, creating a seamless connection between the roads you drive, the places you visit and the Tuscany you experience along the way.

Accommodation Inclusions Dolce Vita Multi-Day Tours

Accommodation Inclusions – Dolce Vita Multi-Day Tours

FAQs - Classic Car Tours in Tuscany

What is included in a TuscanTeam Classic Car Tour in Tuscany?

Our classic car tours combine the use of a classic Italian car with carefully planned scenic driving routes and the support of a TuscanTeam Tour Manager in a pilot car.

Depending on the selected experience, the package may also include fuel, transfers, accommodation, luggage transportation, wineries, meals and selected local experiences. The exact inclusions are clearly specified in each individual itinerary.

Is this a classic car rental or a guided driving experience?

Our Classic Car Tours are designed as complete guided driving experiences, rather than simple car rentals. You drive your own classic car while a TuscanTeam Tour Manager leads the route in a separate pilot car. We plan the itinerary, driving times, stops and logistics so that you can concentrate on enjoying the car and the Tuscan roads.

Are the classic cars manual or automatic?

Our Italian classic cars from the 1960s and 1970s are predominantly manual transmission. Drivers should therefore be confident and experienced driving a manual car. Classic cars also require a different driving style from modern vehicles, and we provide an introduction to the car before departure.

How many guests can travel in each classic car?

Most of the classic convertibles used for our driving experiences accommodate two guests per car. This makes the tours particularly suitable for couples travelling together, as well as groups of friends using several cars. The exact capacity depends on the model selected and is confirmed when arranging your tour.

Can we book a one-day Classic Car Tour?

Yes. Our One-Day Classic Car Driving Tours are available for private groups with a minimum of three cars. The experience includes a planned scenic route and a TuscanTeam Tour Manager leading the group in a pilot car. Classic cars can also be delivered to your hotel, villa or countryside accommodation when the location and road access are suitable.

Does a Tour Manager accompany us during the drive?

Yes. During scheduled driving days, a TuscanTeam Tour Manager leads the experience in a pilot car, guiding the group along the planned route and coordinating timing, stops and logistics. You remain behind the wheel of your own classic car and follow the pilot car throughout the driving itinerary.

Is mechanical assistance provided during the tour?

The level of mechanical support depends on the size and structure of the tour. For larger private groups travelling with several classic cars, a dedicated support vehicle with a mechanic can accompany the driving experience when required. For smaller tours, assistance is coordinated according to the itinerary and the vehicles being used.

Is insurance included and is there an insurance excess?

The classic cars are provided with the insurance coverage required for the rental. However, each vehicle is subject to an insurance excess (damage liability) that must be guaranteed by the driver. Depending on the selected vehicle, the excess generally ranges from €1,500 to €5,000 per car. The exact amount and applicable rental conditions are confirmed before booking.

Where do we stay during the multi-day Dolce Vita Tours?

Our multi-day tours use a selected collection of boutique wine resorts, country hotels and historic countryside properties. Accommodation is chosen not only for atmosphere and quality but also for its strategic position along the driving route. This allows us to minimise unnecessary transfers and keep you close to the scenic roads and experiences planned for each day. For itineraries using more than one property, luggage transportation can be arranged between accommodations when included in the selected package.

Can TuscanTeam create a custom Classic Car Tour for our group?

Yes. We can design private and custom classic car journeys according to your travel dates, group size, accommodation and the areas of Tuscany you would like to explore. Custom experiences can include multiple classic cars, tailored driving routes, accommodation, private transfers, luggage logistics, wineries, meals and selected Tuscan experiences. They are particularly suitable for groups of friends, families, private celebrations, corporate groups and incentive travel.

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