3 days Tuscany classic cars driving tour

3-Day Dolce Vita Classic Car Tour in Tuscany

A Short Classic Car Journey into the Tuscan Dolce Vita

Imagine leaving the ordinary behind and spending three days discovering Tuscany from the driver’s seat of a classic Italian convertible. Country roads wind between vineyards and olive groves, medieval villages appear on distant hilltops, and the journey itself becomes as memorable as every destination along the way.

The 3-Day Dolce Vita Classic Car Tour in Tuscany is designed as a short but immersive escape combining two days behind the wheel with two nights in handpicked countryside accommodation. It is an ideal way to experience the pleasure of classic-car driving while still enjoying the wine, food, landscapes and relaxed rhythm that define the Tuscan lifestyle.

Rather than covering long distances, the journey concentrates on some of the most rewarding roads in the Chianti and Siena countryside, where the landscape changes continuously between vineyards, forests, stone villages and panoramic valleys.

Two Days Behind the Wheel

During the scheduled driving days, you take the wheel of your own classic Italian car while a TuscanTeam Tour Manager leads the route in a pilot car. The itineraries are carefully planned around scenic country roads, enjoyable driving distances and meaningful stops along the way. The objective is not simply to travel from one destination to another, but to make the road an essential part of the experience.

You can enjoy the character of a vintage car without having to concentrate on navigation or planning the day’s logistics. Your Tour Manager coordinates the route, timing and scheduled stops, allowing you to focus on the pleasure of driving through Tuscany.

The pace is deliberately relaxed. There is time to drive, but also time to stop, explore and enjoy the places encountered along the journey.

More Than a Classic Car Driving Tour

The Dolce Vita experience continues after you leave the driver’s seat. Selected wine experiences, Tuscan lunches, historic villages and countryside stops are incorporated into the itinerary, creating a journey that combines driving with the culture and lifestyle of the region.

At the end of the day, return to a carefully selected boutique wine resort or country hotel, chosen both for its atmosphere and for its strategic location along the driving route. This combination allows you to experience Tuscany as a complete journey: drive through its landscapes during the day, discover its wines and cuisine along the way, and spend the evening surrounded by the countryside you have just explored.

Discover more about our collection of Classic Car Tours in Tuscany

Designed for Couples and Small Private Groups

The 3-Day Dolce Vita experience is particularly suited to couples looking for a romantic Tuscan escape and friends who want to share the journey in several classic cars. With two guests in most of our classic convertibles, each couple enjoys their own car while travelling together as part of the driving experience.

The compact three-day format also makes the tour easy to incorporate into a longer Italian itinerary. It can become a countryside escape between stays in Florence, Rome or another Italian destination, without requiring an entire week dedicated to driving.

For travellers who want more time on the road and the opportunity to explore a broader area of Tuscany, the journey can also be extended into our 5-Day Dolce Vita Classic Car Tour.

Three days, two days behind the wheel and one simple philosophy: enjoy the road, embrace the landscape and experience Tuscany in true Dolce Vita style.

All about the 3-Day Dolce Vita Classic Car Tour in Tuscany.

3 Days of Classic Cars, Wine Country & Tuscan Lifestyle

The 3-Day Dolce Vita Classic Car Tour is a short private journey designed for travellers who want to experience the pleasure of driving a classic Italian car without dedicating an entire week to a road trip.

The experience combines three days and two nights in the Tuscan countryside with two dedicated classic-car driving days, following scenic routes through some of the most beautiful landscapes of Chianti and the Siena countryside.

Rather than simply travelling between destinations, the itinerary has been designed around roads that are enjoyable to drive. Vineyards, olive groves, medieval villages and panoramic countryside become part of the journey as you follow your TuscanTeam Tour Manager in a pilot car.

Two Classic Car Driving Days

Your classic car is at the heart of the experience. During the two 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.

Driving distances are intentionally balanced to leave time for the other elements of the journey. The objective is not to cover as many kilometres as possible, but to enjoy the character of the car and the landscapes through which you are travelling.

Wine, Food & the Tuscan Countryside

A Dolce Vita journey is about more than driving. The experience combines the road with selected Tuscan wineries, wine tastings, local cuisine and historic villages, creating natural breaks between different sections of the drive. Lunch becomes part of the journey rather than simply a scheduled stop, while time away from the car allows you to discover the wine country and places encountered along the route.

Two Nights in Handpicked Countryside Accommodation

Your two nights are spent in a carefully selected boutique wine resort or country hotel, chosen for its character, setting and strategic location in relation to the driving routes.

Staying in the countryside allows the experience to continue after the cars are parked, with vineyards, Tuscan landscapes and local cuisine forming part of the atmosphere of the journey.

A Short Escape Within a Longer Italian Journey

With its compact three-day format, this experience can easily become part of a longer vacation in Italy. It is particularly suited to couples and friends who want to leave the cities behind for a few days, experience the Tuscan countryside from behind the wheel and then continue towards Florence, Rome or another destination.

For travellers looking for a longer road journey, the 5-Day Dolce Vita Classic Car Tour extends the experience with three driving days and a broader exploration of 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 3-Day Dolce Vita Classic Car Tour

Your 3-Day Dolce Vita experience combines two classic-car driving days, two nights in the Tuscan countryside and carefully selected food, wine and travel services.

Classic Car & Driving Experience

✔ Classic Italian convertible for 2 scheduled driving days
✔ TuscanTeam Tour Manager leading the journey in a pilot car
✔ Carefully planned scenic driving routes through the Tuscan countryside
✔ 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

✔ 2 nights in a handpicked boutique wine resort or country hotel
✔ Double room accommodation for 2 guests
✔ Daily breakfast
✔ Private bathroom
✔ Convenient parking for the classic cars
✔ Accommodation strategically selected according to the driving itinerary and logistics

Food & Wine Experiences

✔ 2 Tuscan lunches
✔ 2 Tuscan dinners
✔ Selected winery visit and cellar experience
✔ Guided wine tasting
✔ Wine pairing where specified in the itinerary
✔ Selected local food and wine experiences along the driving route

Transportation & Logistics

✔ Private arrival transfer from Florence to the Tuscan countryside
✔ Private departure transfer to Florence or the agreed drop-off point
✔ Luggage transportation when required by the itinerary
✔ On-trip logistical coordination and TuscanTeam assistance

Important Driving Information

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.

What is not included in this tour?Items that are not included in the cost of tour price.

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Day 1 Welcome to Tuscany & Your First Classic Car Drive

From Florence to the Tuscan Countryside

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

Leave the city behind as the landscape gradually changes into vineyards, olive groves, cypress-lined roads and medieval hilltop villages. On arrival at your handpicked boutique wine resort or country hotel, complete check-in and prepare for the first highlight of your journey: meeting your classic Italian car.

Your TuscanTeam Tour Manager will introduce you to the vehicle and provide a short driving briefing before taking the lead in the pilot car.

Then it is your turn to take the wheel.

Your first route is designed as an enjoyable introduction to both the classic car and Tuscany’s scenic country roads. Follow the pilot car through the Chianti and Siena countryside, where winding roads connect vineyards, small villages and panoramic landscapes.

Along the way, stop for your first Tuscan lunch, enjoying local cuisine before returning to the road for the afternoon drive.

There is no need to think about navigation or finding the right roads. Your Tour Manager leads the journey and coordinates the route, timing and planned stops, leaving you free to concentrate on the experience behind the wheel.

Return to your countryside accommodation in the late afternoon, park your classic car and enjoy time to relax.

The day concludes with your first included Tuscan dinner, surrounded by the peaceful atmosphere of the countryside.

Highlights: Private arrival from Florence, classic-car introduction, first driving experience, Chianti and Siena countryside, panoramic roads and Tuscan cuisine.

Included Services: Private transfer from Florence, classic car, driving briefing, TuscanTeam Tour Manager and pilot car, fuel, planned driving route, Tuscan lunch, Tuscan dinner and overnight accommodation.
Day 2 Chianti Wine Country & The Dolce Vita Road

Classic Cars, Vineyards & Tuscan Wine

After breakfast, return to your classic car for a full day dedicated to some of Tuscany’s most rewarding driving roads.

Following your TuscanTeam pilot car, travel deeper into Chianti wine country, where winding roads move naturally between vineyards, forests, historic estates and medieval villages.

The itinerary has been designed around the pleasure of driving rather than simply connecting one destination with another. Along the way, there is time for panoramic stops and moments to enjoy the villages and countryside encountered during the journey.

One of the highlights of the day is a visit to a selected Tuscan winery. Discover the estate and its wines before sitting down for your second Tuscan lunch, accompanied by a guided wine tasting and pairing.

After lunch, the journey continues through a different section of the countryside, giving you another opportunity to enjoy the character of your vintage car and the changing Tuscan landscape.

Return to your wine resort or country hotel in the late afternoon. Once the cars are parked, the evening is yours to slow down and enjoy your second included Tuscan dinner.

Highlights: Full classic-car driving day, Chianti wine country, panoramic roads, winery experience, wine tasting and Tuscan cuisine.

Included Services: Breakfast, classic car, TuscanTeam Tour Manager and pilot car, fuel, planned driving route, winery visit and tasting, Tuscan lunch with wine pairing, Tuscan dinner, overnight accommodation.
Day 3 A Slow Tuscan Morning & Departure

Farewell Breakfast and Toast to Our Journey On the final day of your romantic escapade, gather for a farewell breakfast where you’ll reflect on the unforgettable moments of your journey. Raise a glass to the memories created and the love shared during this extraordinary adventure before parting ways.

Handpicked Accommodation in the Tuscan Countryside

Your 2-night stay is an integral part of the 3-Day Dolce Vita Classic Car Tour.

TuscanTeam selects boutique wine resorts, country hotels and historic countryside properties located in strategic areas between Chianti and the Siena countryside, allowing the accommodation to become a natural base for the two classic-car driving days.

Properties are chosen not only for their atmosphere, character and quality, but also for their location and accessibility by classic car. Convenient road access and suitable parking are particularly important when travelling with vintage vehicles.

Staying in the countryside also allows the Dolce Vita experience to continue after the driving day is over. Once the cars are parked, you can relax among vineyards and Tuscan landscapes, enjoy dinner and experience the slower rhythm of rural Tuscany.

Rather than selecting a hotel independently from the itinerary, we match the accommodation with the planned driving routes. This helps reduce unnecessary transfers and positions you close to the scenic roads, wineries, villages and experiences included in the journey.

Depending on availability and the selected travel dates, TuscanTeam proposes the most suitable property for your itinerary, always considering the balance between location, character, comfort and driving logistics.

Accommodation Inclusions

✔ 2 nights in a handpicked boutique wine resort or country hotel
✔ Double room accommodation for 2 guests
✔ Daily breakfast
✔ Private bathroom
✔ Convenient parking for the classic car
✔ Property strategically located according to the driving itinerary
✔ Accommodation taxes, except local city tax where payable directly at the property

FAQ – 3-Day Dolce Vita Classic Car Tour

How does the 3-Day Dolce Vita Classic Car Tour work?

The experience includes three days, two nights and two classic-car driving days.

On Day 1, you arrive from Florence by private transfer, meet your classic car and begin your first scenic drive through the Tuscan countryside. Day 2 is dedicated to a full classic-car driving experience combined with wine country, a selected winery and Tuscan cuisine. Day 3 is a relaxed departure day with a private transfer to Florence or the agreed drop-off point.

How many days will we actually drive the classic car?

You will drive your classic car on two scheduled driving days: Day 1 and Day 2. Driving distances and routes are carefully planned to balance time behind the wheel with lunches, winery experiences, scenic stops and time to enjoy the Tuscan countryside.

Do we drive the classic car 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, following the planned route and coordinating navigation, timing and scheduled stops. This allows you to concentrate on driving rather than finding your way through unfamiliar country 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 with a manual gearbox. Before departure, 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 travelling from outside the European Union may also be required to carry an International Driving Permit (IDP) or an official translation of their driving licence, depending on the country in which the licence 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. The specific documentation and rental conditions are confirmed before booking.

How many people can travel in each classic car?

Most of the classic convertibles used for the Dolce Vita experience accommodate two guests per car, making the tour particularly suited to couples. Friends travelling together can enjoy the journey with multiple cars, following the TuscanTeam pilot car as a private driving group.

What accommodation is included?

The package includes two nights in a handpicked boutique wine resort or country hotel in the Tuscan countryside, with daily breakfast. Properties are selected for their character and comfort as well as their strategic location, suitable road access and convenient parking for the classic cars.

Are lunches and dinners included?

Yes. The 3-Day Dolce Vita package includes two Tuscan lunches and two Tuscan dinners. The journey also includes a selected winery experience and wine tasting, with wine pairing where specified in the itinerary.

Are transfers from Florence included?

Yes. The package includes a private arrival transfer from Florence to the Tuscan countryside and a private departure transfer to Florence or the agreed drop-off point. This allows you to begin and finish the experience without having to organise separate transportation or manage luggage while driving the classic car.

Is fuel included?

Yes. Fuel for the scheduled classic-car driving itinerary 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, however, subject to an insurance excess (damage liability) that must be guaranteed by the driver. Depending on the selected classic car, the excess generally ranges from €1,500 to €5,000 per vehicle. The exact amount and rental conditions are confirmed before booking.

Can we extend the experience or add extra nights?

Yes. The 3-Day tour can be incorporated into a longer private journey in Tuscany, with additional nights, transfers and experiences arranged around your travel plans. Travellers who want a longer classic-car journey can also choose the 5-Day Dolce Vita Classic Car Tour, which extends the experience to three driving days and explores a broader area of Tuscany.

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Your Travel Experience Inclusions	Price Excluding Flights
3-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 2 classic car driving days, 2 nights in a handpicked boutique wine resort or country hotel, private transfers, 2 Tuscan lunches, 2 Tuscan dinners, winery and wine tasting experience, professional pilot car and TuscanTeam assistance throughout the journey.	7.720 €	Book Now
3-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 2 classic car driving days, 2 nights in a handpicked boutique wine resort or country hotel, shared private transfers, 2 Tuscan lunches and 2 Tuscan dinners per guest, winery and wine tasting experience, professional pilot car and TuscanTeam assistance throughout the journey.	11.900 €	Book Now
3-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 2 classic car driving days, 2 nights in a handpicked boutique wine resort or country hotel, shared private transfers, 2 Tuscan lunches and 2 Tuscan dinners per guest, winery and wine tasting experience, professional pilot car and TuscanTeam assistance throughout the journey.	16.110 €	Book Now