5-Day Dolce Vita Classic Car Tour in Tuscany

A Classic Car Journey Through the Heart of Tuscany

There are journeys where the destination matters, and others where the road becomes part of the experience. The 5-Day Dolce Vita Classic Car Tour in Tuscany is designed around exactly that idea: five days travelling through the Tuscan countryside, with three dedicated classic-car driving days and four nights in carefully selected country hotels and wine resorts.

Behind the wheel of a classic Italian convertible, you will travel through some of Tuscany’s most celebrated landscapes, from the vineyards and medieval villages of Chianti and Siena to the rolling hills of Val d’Orcia and Montalcino. Rather than returning to the same base every evening, the journey develops naturally across the region. Different landscapes, roads, wine areas and countryside properties become part of a genuine Tuscan road trip, allowing you to experience the changing character of Tuscany as you travel south.

Explore our complete collection of Classic Car Tours in Tuscany, from private driving days to multi-day Dolce Vita journeys.

Three Days Behind the Wheel

The heart of the journey is formed by three carefully planned classic-car driving days. Take the wheel of your own vintage Italian car while your TuscanTeam Tour Manager leads the journey in a pilot car, guiding you along scenic country roads selected for the pleasure of driving rather than simply for reaching the next destination. The routes avoid making long distances the objective. Instead, each driving day combines enjoyable stretches behind the wheel with panoramic stops, historic villages and selected experiences along the way.

From the vineyard-covered hills of Chianti to the open landscapes and cypress-lined roads of Val d’Orcia, every section of the journey has its own character. Your Tour Manager coordinates navigation, timing and logistics throughout the scheduled driving days, leaving you free to concentrate on the car, the road and the landscape around you.

From Chianti to Val d’Orcia

One of the defining features of the 5-Day Dolce Vita journey is its progression through different areas of Tuscany. The experience begins among the vineyards and hilltop villages of Chianti and the Siena countryside, before travelling towards Montalcino, home of Brunello wine, and into the UNESCO-listed landscapes of Val d’Orcia.

Wine estates, medieval villages and countryside stops create natural breaks between the driving sections, while selected Tuscan lunches and dinners allow food and wine to become part of the journey rather than simply an addition to it. The result is a road trip in which each day reveals a different side of Tuscany.

Handpicked Countryside Stays Along the Route

Accommodation is carefully integrated into the itinerary.Rather than selecting hotels independently from the driving experience, TuscanTeam works with a collection of boutique wine resorts, historic country hotels and countryside properties positioned along the route.

Properties are selected for their atmosphere and comfort, but also for practical considerations such as location, road access and parking for the classic cars. This allows each overnight stay to become a natural continuation of the journey while reducing unnecessary transfers and positioning you close to the roads and experiences planned for the following day.

The Complete Dolce Vita Driving Experience

The 5-Day tour is particularly suited to couples travelling together and small private groups who want classic-car driving to become one of the central experiences of their journey through Italy. With three days behind the wheel, there is enough time to develop a relationship with the car and enjoy a broader variety of roads and landscapes, while still maintaining a relaxed rhythm throughout the journey.

For travellers with less time available, the 3-Day Dolce Vita Classic Car Tour offers a shorter introduction to the same style of travel.

The 5-Day journey, however, is about going further: five days through Tuscany, three days behind the wheel and a road trip inspired by the timeless spirit of the Italian Dolce Vita.

All about the 5-Day Dolce Vita Classic Car Tour in Tuscany.

5 Days of Classic Cars, Wine Country & Tuscan Landscapes

The 5-Day Dolce Vita Classic Car Tour is a complete road journey combining five days, four nights and three dedicated classic-car driving days through some of Tuscany’s most celebrated landscapes.

The experience develops from the vineyards and medieval villages of Chianti and the Siena countryside towards Montalcino and Val d’Orcia, creating a natural progression through different landscapes, wine regions and driving roads.

Rather than covering long distances simply to reach the next destination, each stage is designed around the pleasure of the journey, balancing time behind the wheel with wineries, Tuscan cuisine, historic villages and moments to slow down and enjoy the countryside.

Three Classic Car Driving Days

Your classic Italian car becomes the connecting thread throughout the journey. During the three scheduled driving days, you take the wheel while your TuscanTeam Tour Manager leads the route in a pilot car, coordinating navigation, timing and planned stops.

Each day introduces a different driving environment. The vineyard-covered hills and winding roads of Chianti gradually give way to the countryside surrounding Siena, before the journey continues south towards the wider landscapes and cypress-lined roads of Val d’Orcia. Routes are carefully planned around enjoyable driving distances, allowing enough time to appreciate both the car and the places encountered along the way.

A Journey Through Tuscany’s Wine Country

Wine and food are an integral part of the Dolce Vita experience. The itinerary travels through some of Tuscany’s most important wine territories, combining the driving journey with selected wineries, cellar visits, wine tastings and Tuscan lunches and dinners.

From Chianti wine country to the hills surrounding Montalcino, these experiences provide natural pauses between driving sections and an opportunity to discover the landscape through its wines, cuisine and local traditions.

Four Nights Along the Driving Route

The journey includes four nights in handpicked boutique wine resorts, country hotels and historic countryside properties.

Accommodation is selected according to the progression of the itinerary rather than independently from it. Location, atmosphere, road access and suitable parking for the classic cars all form part of the selection process. This allows the journey to move naturally through Tuscany while reducing unnecessary transfers and positioning you close to the scenic roads and experiences planned for each stage.

A True Tuscan Road Journey

The 5-Day Dolce Vita Tour is designed for travellers who want more than a single driving experience. With three days behind the wheel and five days immersed in the Tuscan countryside, there is time to experience different roads and landscapes while maintaining the relaxed pace that defines the journey.

It is particularly suited to couples travelling together and small private groups, with each couple enjoying their own classic car while sharing the road, meals and experiences as part of the journey.

For travellers with less time available, the 3-Day Dolce Vita Classic Car Tour offers a shorter countryside escape. The 5-Day experience goes further, transforming the classic car into the thread connecting an entire journey through 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 Your 5-Day Dolce Vita Classic Car Tour

Your 5-Day Dolce Vita journey combines three classic-car driving days, four nights in the Tuscan countryside and carefully selected food, wine and travel experiences along the route.

Classic Car & Driving Experience

✔ Classic Italian convertible for 3 scheduled driving days
✔ TuscanTeam Tour Manager leading the journey in a pilot car
✔ Carefully planned scenic driving routes through Tuscany
✔ Route planning and driving-day coordination
✔ Fuel for the scheduled driving itinerary
✔ Parking and road tolls where required along the planned route
✔ Introduction to your classic car before departure

Accommodation

✔ 4 nights in handpicked boutique wine resorts, country hotels or historic countryside properties
✔ Double room accommodation for 2 guests
✔ Daily breakfast
✔ Private bathroom
✔ Convenient parking for the classic cars
✔ Properties strategically selected according to the progression of the driving itinerary
✔ Accommodation and luggage logistics coordinated between different stages of the journey

Food & Wine Experiences

✔ 3 Tuscan lunches – Days 2, 3 and 4
✔ 2 Tuscan dinners – Days 1 and 4
✔ Selected winery visits and cellar experiences
✔ Guided wine tastings
✔ Wine pairing where specified in the itinerary
✔ Selected food and wine experiences across Chianti, Montalcino and the Tuscan countryside

Transportation & Travel Logistics

✔ Private arrival transfer from Florence to the starting accommodation
✔ Private departure transfer to Florence or the agreed drop-off point
✔ Luggage transportation between accommodations when required
✔ On-trip logistical coordination throughout the journey
✔ TuscanTeam assistance during scheduled travel services

Important Driving Information

The classic cars are provided with the insurance coverage required for the rental. 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 exact amount and applicable rental conditions are confirmed before booking.

Day 1 Welcome to Tuscany

Florence to the Chianti & Siena Countryside

Your Dolce Vita journey begins in Florence, where your private driver meets you for the transfer into the Tuscan countryside.

As you leave the city behind, the landscape gradually changes into vineyards, olive groves, stone farmhouses and cypress-lined roads. Your destination is a handpicked boutique wine resort or country hotel strategically positioned between the Chianti and Siena countryside, ready for the classic-car journey ahead.

After check-in, the rest of the afternoon is yours to settle into the slower rhythm of Tuscany. Relax at the property, explore the surrounding countryside or simply enjoy your first views across the Tuscan hills.

In the evening, come together for your first included Tuscan dinner, introducing the wines, flavours and atmosphere that will accompany the journey over the coming days. Tomorrow, the road begins.

Highlights: Private arrival from Florence, Chianti and Siena countryside, handpicked country accommodation and welcome Tuscan dinner.

Included Services: Private transfer from Florence, accommodation, welcome dinner and TuscanTeam travel assistance.
Day 2 Siena Countryside to Montalcino

Medieval Villages, Scenic Roads & Brunello Wine Country

After breakfast, meet your TuscanTeam Tour Manager and get ready for the first day behind the wheel of your classic Italian convertible. Following an introduction to the car and a short driving briefing, set off behind the pilot car and begin your journey south through the beautiful Siena countryside.

Today’s route is designed as a genuine classic-car journey rather than a simple transfer. Follow carefully selected country roads through rolling hills, vineyards and cypress-lined landscapes, passing medieval villages and some of the lesser-known corners of central Tuscany along the way.

As you become familiar with the character of your classic car, enjoy a relaxed rhythm behind the wheel, with panoramic stops and time to appreciate the changing landscape.

During the journey, stop for your first included Tuscan lunch, taking time to enjoy the local cuisine before returning to the road. In the afternoon, continue south towards Montalcino, where vineyards begin to dominate the landscape and announce your arrival in one of Italy’s most celebrated wine regions.

Famous throughout the world as the home of Brunello di Montalcino, this historic hilltop town and its surrounding countryside provide the setting for the next stage of your Dolce Vita journey.

Arrive at your handpicked wine resort in the Brunello region in the late afternoon. While you enjoy the journey behind the wheel, TuscanTeam coordinates the transfer of your luggage to the new accommodation.

Park your classic car and enjoy the evening at leisure, surrounded by vineyards and the peaceful countryside of Montalcino.

Highlights: First classic-car driving day, Siena countryside, medieval villages, cypress-lined roads, scenic Tuscan landscapes, Montalcino and Brunello wine country.

Included Services: Breakfast, classic car, driving briefing, TuscanTeam Tour Manager and pilot car, fuel, planned driving route, luggage transportation, Tuscan lunch and overnight accommodation in the Brunello wine region.
Day 3 Val d’Orcia & Pienza

Driving Through Tuscany’s Most Iconic Landscape

Wake up surrounded by the countryside of the Brunello wine region and prepare for your second day behind the wheel.

After breakfast, meet your TuscanTeam Tour Manager and set off in your classic Italian car towards the Val d’Orcia, one of Tuscany’s most celebrated landscapes and a UNESCO World Heritage Site.

Follow the pilot car along panoramic country roads as vineyards and wooded hills gradually open into wide valleys, isolated farmhouses and long rows of cypress trees. This is one of the most rewarding areas of Tuscany to experience from behind the wheel of a classic convertible, where the road itself becomes part of the landscape.

The route leads towards Pienza, the Renaissance hilltop town overlooking the Val d’Orcia. Park the cars and take time to explore its historic centre, small streets and panoramic viewpoints, with magnificent views stretching across the surrounding countryside.

Pienza is also closely associated with Pecorino di Pienza, the traditional sheep’s milk cheese produced in this part of Tuscany. Your included Tuscan lunch offers an opportunity to enjoy the flavours of the territory before returning to the road.

In the afternoon, continue your classic-car journey through a different section of Val d’Orcia, following scenic roads through the rolling hills before making your way back towards the Montalcino and Brunello wine region.

Return to your handpicked wine resort in the late afternoon, park the cars and enjoy the evening at leisure surrounded by the peaceful Tuscan countryside.

Highlights: Second classic-car driving day, Val d’Orcia UNESCO landscape, Pienza, panoramic country roads, cypress-lined scenery and local Tuscan flavours.

Included Services: Breakfast, classic car, TuscanTeam Tour Manager and pilot car, fuel, planned driving route, Tuscan lunch and overnight accommodation in the Brunello wine region.
Day 4 Val d’Orcia to Chianti Classico

Wine Roads, Medieval Villages & the Final Classic Car Drive

After breakfast, take the wheel of your classic Italian car for the third and final driving day of your Dolce Vita journey.

Leaving the open landscapes of Val d’Orcia behind, follow your TuscanTeam Tour Manager north towards the vineyard-covered hills of Chianti Classico. Today is both a journey between two different areas of Tuscany and a final opportunity to enjoy the pleasure of driving along carefully selected country roads.

As you travel north, the landscape gradually changes. Wide valleys and rolling farmland give way to forests, vineyards, stone farmhouses and the medieval hilltop villages that characterise the heart of Chianti.

Along the route, stop at a selected Chianti Classico winery for a private visit of the historic cellars. Discover the estate, learn about the traditions and techniques behind Chianti Classico production and enjoy a guided tasting of its wines.

Your third included Tuscan lunch is enjoyed during the journey, providing time to slow down and experience the food and wine culture of the region before returning to the road.

The afternoon continues through the heart of what is sometimes affectionately known as “Chiantishire”, with time to discover picturesque medieval villages and enjoy the final panoramic roads of your classic-car adventure.

Meanwhile, TuscanTeam takes care of the luggage transfer from Val d’Orcia to Chianti, allowing you to travel comfortably with the classic car.

Arrive at your handpicked Chianti wine resort or country hotel in the late afternoon and return the cars after three unforgettable days behind the wheel.

Tonight, celebrate the conclusion of your driving journey with your second included Tuscan dinner and a final evening surrounded by the vineyards and countryside of Chianti.

Highlights: Val d’Orcia to Chianti road journey, third classic-car driving day, Chianti Classico wine country, private winery and cellar visit, wine tasting, medieval villages and final Dolce Vita dinner.

Included Services: Breakfast, classic car, TuscanTeam Tour Manager and pilot car, fuel, planned driving route, luggage transportation, private Chianti Classico winery visit, wine tasting, Tuscan lunch, Tuscan dinner and overnight accommodation in Chianti.
Day 5 Farewell Tuscany

A Final Morning in Chianti

Wake up to your final morning surrounded by the vineyards and rolling hills of Chianti.

After three days behind the wheel and a journey that has taken you through the Siena countryside, Montalcino, Val d’Orcia and Chianti Classico, enjoy a relaxed farewell breakfast at your country hotel or wine resort.

Take time to reflect on the roads travelled, the landscapes discovered and the experiences shared along the way — from medieval villages and cypress-lined roads to Brunello wine country and the vineyards of Chianti.

With the classic-car journey now complete, check out from your accommodation and prepare to continue with the next stage of your Italian vacation.

Your private driver will meet you for the transfer to Florence or your agreed drop-off point, while TuscanTeam coordinates the final travel logistics.

You leave Tuscany with the memories of five days spent travelling at a different pace — three days behind the wheel, four nights in the countryside and a journey through some of the most beautiful landscapes of Tuscany.

Highlights: Farewell breakfast, final morning in Chianti and conclusion of your Dolce Vita journey.

Included Services: Breakfast, check-out assistance, private departure transfer to Florence or the agreed drop-off point and TuscanTeam travel assistance.

Handpicked Accommodation Along Your Classic Car Journey

Accommodation is an integral part of the 5-Day Dolce Vita Classic Car Tour. Rather than returning to the same hotel every evening, the journey combines carefully selected properties positioned along the driving route.

Your four nights are spent in handpicked boutique wine resorts, country hotels and historic countryside properties, selected to complement the different landscapes explored during the journey.

The itinerary begins in the Chianti and Siena countryside, continues into the Brunello wine region around Montalcino, and concludes among the vineyards and rolling hills of Chianti Classico.

Each property is selected not only for its character, atmosphere and comfort, but also for its strategic location within the driving itinerary. Road access, suitable parking for the classic cars and proximity to the following day’s route are all important considerations.

This approach allows the accommodation to become part of the journey itself. As the landscape changes, so does the setting of your stay — from vineyard-covered hills to the open countryside of southern Tuscany and back to the heart of Chianti wine country.

When the journey moves from one property to another, TuscanTeam coordinates the luggage transfer, allowing you to enjoy the classic car with only what you need for the day. Your main luggage travels separately and is delivered to your next accommodation.

The result is a seamless road journey where cars, roads, accommodation and experiences are planned together, rather than as separate elements of the trip.

The tour package inclusions and exclusions at a glance.

Accommodation Inclusions

✔ 4 nights in handpicked boutique wine resorts, country hotels or historic countryside properties
✔ Double room accommodation for 2 guests
✔ Daily breakfast
✔ Private bathroom
✔ Convenient parking for the classic cars
✔ Properties strategically selected along the driving itinerary
✔ Accommodation logistics coordinated throughout the journey
✔ Luggage transportation between properties when changing accommodation
✔ Accommodation taxes, except local city tax where payable directly at the property

What's not included into your Dolce Vita Experience ?Items that are not included in the cost of tour price.

Dinners Not Included: Being a Small Group Tour we leave you the space to enjoy 3 evening as you please.

FAQ – 5-Day Dolce Vita Classic Car Tour

How does the 5-Day Dolce Vita Classic Car Tour work?

The experience includes five days, four nights and three classic-car driving days through different areas of Tuscany. After arriving in the Tuscan countryside on Day 1, you drive on Days 2, 3 and 4, travelling through the Siena countryside, Montalcino, Val d’Orcia, Pienza and Chianti Classico. Day 5 is dedicated to breakfast and your private departure transfer.

How many days will we actually drive the classic car?

You will drive your classic car on three scheduled driving days: Days 2, 3 and 4. Each route is designed to balance enjoyable driving distances with scenic stops, medieval villages, food and wine experiences and time to enjoy the Tuscan countryside.

Is this a road trip or do we return to the same hotel every night?

This is a genuine classic-car road journey through Tuscany. The itinerary uses different handpicked countryside properties positioned along the route. You travel from the Chianti and Siena countryside towards the Brunello wine region and Val d’Orcia, before returning through Chianti Classico on the final driving day. TuscanTeam coordinates the accommodation and luggage logistics between the different stages of the journey.

Do we drive the classic cars ourselves?

Yes. You will be behind the wheel of your own classic Italian car. A TuscanTeam Tour Manager leads the journey in a pilot car, coordinating the planned route, navigation, timing and scheduled stops throughout the three driving days.

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. Before the first driving day, we provide an introduction to the vehicle and its controls.

What driving licence do I need to drive a classic car in Italy?

Drivers must hold a valid driving licence appropriate for the vehicle being driven. Guests whose driving licence was issued outside the European Union may also be required to carry an International Driving Permit (IDP) or an official translation of their licence, depending on the country where it was issued and current Italian regulations.

For guests travelling from the United States, we recommend obtaining an International Driving Permit before travelling to Italy and carrying it together with the original US driving licence. All drivers must also meet the age and driving requirements applicable to the selected classic car. Specific documentation and rental conditions are confirmed before booking.

How many guests can travel in each classic car?

Most classic convertibles used for the Dolce Vita experience accommodate two guests per car. This makes the journey particularly suitable for couples, while friends or small private groups can travel together using multiple classic cars and following the TuscanTeam pilot car.

What accommodation is included?

The package includes four nights in handpicked boutique wine resorts, country hotels or historic countryside properties, with daily breakfast. Accommodation is selected according to the progression of the driving route, with particular attention to atmosphere, location, road access and suitable parking for the classic cars.

What happens to our luggage while we drive?

TuscanTeam coordinates luggage transportation between accommodations when the itinerary moves from one property to another. This allows you to enjoy the classic-car journey without having to carry your main luggage in the vehicle. Your bags are transferred separately and will be waiting at the next accommodation.

Are lunches and dinners included?

Yes. The package includes three Tuscan lunches on Days 2, 3 and 4, and two Tuscan dinners on Days 1 and 4. Selected wine experiences and tastings are also included as specified in the itinerary.

Are transfers from Florence included?

Yes. A private arrival transfer from Florence to your first countryside accommodation and a private departure transfer to Florence or the agreed drop-off point are included. This creates a seamless journey from arrival through to the end of the tour.

Is fuel included?

Yes. Fuel for all three scheduled classic-car driving days is included, together with route planning, the TuscanTeam pilot car and driving-day coordination.

Is insurance included and is there an insurance excess?

The classic cars are provided with the insurance coverage required for the rental. 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 exact amount and applicable rental conditions are confirmed before booking.

Can the 5-Day Dolce Vita Tour be customized?

Yes. The journey can be adapted according to your travel dates, group size, accommodation preferences and wider Italian itinerary, subject to the logistics required for the classic cars. Additional nights, private transfers and selected experiences can also be incorporated into a longer custom-made journey through Italy.

What if five days are too long for our itinerary?

For travellers with less time available, the 3-Day Dolce Vita Classic Car Tour offers a shorter experience with two driving days and two nights in the Tuscan countryside.

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Your Travel Experience Inclusions	Price Excluding Flights
5-Day Dolce Vita Classic Car Tour for 2 Guests. Price is for the private party of 2 guests sharing 1 classic car and 1 double room. Includes 3 classic car driving days, 4 nights in handpicked boutique wine resorts and country hotels, private transfers, 3 Tuscan lunches, 2 Tuscan dinners, selected winery and wine tasting experiences, professional pilot car, luggage transfers between accommodations and TuscanTeam assistance throughout the journey.	11.100 €	Book Now
5-Day Dolce Vita Classic Car Tour for 4 Guests. Price is for the private party of 4 guests sharing 2 classic cars and 2 double rooms. Includes 3 classic car driving days, 4 nights in handpicked boutique wine resorts and country hotels, shared private transfers, 3 Tuscan lunches and 2 Tuscan dinners per guest, selected winery and wine tasting experiences, professional pilot car, luggage transfers between accommodations and TuscanTeam assistance throughout the journey.	17.900 €	Book Now
5-Day Dolce Vita Classic Car Tour for 6 Guests. Price is for the private party of 6 guests sharing 3 classic cars and 3 double rooms. Includes 3 classic car driving days, 4 nights in handpicked boutique wine resorts and country hotels, shared private transfers, 3 Tuscan lunches and 2 Tuscan dinners per guest, selected winery and wine tasting experiences, professional pilot car, luggage transfers between accommodations and TuscanTeam assistance throughout the journey.	24.700 €	Book Now