Tuscany Classic Car Tour

5-Day Classic Car Driving Tour of Tuscany

Embark on an Unforgettable Classic Car Driving Tour of Tuscany: A 5-Day Exploration

Step into a world of timeless elegance and romance with our Classic Car Driving Tour of Tuscany, a captivating 5-day adventure that promises to transport you to the heart of Italy’s most enchanting region. Picture yourself behind the wheel of a vintage Fiat or Alfa Romeo, a classic 2-seater cabrio, as you embark on an unforgettable journey through Tuscany’s picturesque landscapes and historic towns.

Experience Highlights:

Scenic Routes and Charming Stops: Immerse yourself in the breathtaking beauty of Tuscany as you navigate along scenic routes that wind through rolling hills, vineyards, and centuries-old olive groves. Discover charming historic towns along the way, each offering a glimpse into Tuscany’s rich cultural heritage.

Carefully Curated Accommodations: Indulge in the comfort and luxury of carefully selected accommodations that capture the essence of Tuscany’s charm. From elegant historic villas to cozy boutique inns, each hotel is chosen to provide a relaxing retreat after a day of exploration.

Classic Cars, Timeless Style: Experience the thrill of driving a classic car with our meticulously maintained Fiat or Alfa Romeo 2-seater cabrios. Combining vintage charm with modern comfort, these iconic cars are the perfect companions for your journey through Tuscany’s picturesque countryside.

Tailored Experience, All-Inclusive Package: Enjoy a hassle-free experience with our all-inclusive package, covering all expenses except for dinners. This allows you the freedom to choose your dining experiences and enjoy intimate evenings at your own pace, savoring the flavors of Tuscan cuisine.

Unlock the Charm of Tuscany: With our Classic Car Driving Tour, you’ll unlock the hidden treasures of Tuscany at your own pace. Whether you’re captivated by the art, indulging in world-class wines, or simply reveling in the joy of the open road, this tour offers a unique opportunity to explore Tuscany in style and luxury.

Embark on a journey of discovery and romance with our Classic Car Driving Tour of Tuscany. Book your adventure today and create memories that will last a lifetime as you drive through the timeless landscapes of this iconic Italian region


Indulge in the romance and beauty of Tuscany on this 5-day Vintage Convertible Car Tour. Come, live the “Dolce Vita” with us in the heart of Italy. Indulge in the “dolce vita” and celebrate the beauty of Tuscany with a blend of scenic drives, exquisite dining, wine tastings, and country accommodations. This 5-day getaway is a symphony of romance, culture, and culinary delights that will leave you with a heart full of cherished memories. Book now to embark on this unforgettable journey through the heart of Italy.

Price is intended for each couple sharing 1 double bedroom and 1 car
Are you a solo Solo Traveller ? we offer a 10% discount. Contact us to get the discount.

All about the 5-Day Classic Car Driving Tour of Tuscany.

Experience the allure of Tuscany with our Classic Car Driving Tour. Over 5 days, explore scenic routes and charming towns behind the wheel of a vintage Fiat or Alfa Romeo. Enjoy carefully curated accommodations, from historic villas to boutique inns. Revel in the thrill of driving a classic car while savoring the comfort of modern luxury. Our all-inclusive package covers everything except dinners, offering flexibility for personalized dining experiences. Unlock Tuscany’s charm at your own pace, creating lasting memories against the backdrop of rolling hills and vineyards. Book now for a journey that blends romance, history, and the joy of the open road.

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.

· 4 Overnight stay at 3 Luxury Tuscan Properties with Swimming Pool
. 4* or 5* Hotels and Villas in Montalcino and Chianti wine regions.
. 1 Dinner on Arrival Day with Wines – à la carte
. 4 Traditional Breakfasts
. 3 Luncheons
· 3 Driving journeys through Siena country side, Chianti Wine Region and Val d’Orcia.
· 3 days of 2-seater vintage car rental
· Gasoline, Parking Tolls and luggage transfer when required
· Visits of charming country villages
· 2 hrs Private in depth guided visit of Siena, with local expert guide;
· Private Winery Tour and Wine Pairing Traditional Tuscan Lunch in the Chianti region;
· English Speaking Local Tour Manager leading the driving tour;
· Small Group Travel – Max 3/4 couples-cars
· All Taxes and Vat.

Price is intended for each couple sharing 1 double bedroom and 1 car
Optional Add-ons: Enhance your experience with optional private transfers to join departure place, activities such as hot air balloon rides over the Tuscan countryside,
spa treatments and massages, or guided tours of historical sites.
Are you a solo Solo Traveller: we offer a 10% discount.

What is not included in this tour?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.

  1. Day1 Al Fresco Welcome Dinner at Villa or Hotel.

    As you step into the heart of Tuscany, your romantic journey begins with an al fresco welcome dinner at the enchanting Villa or Hotela. This historic villa, nestled amidst rolling hills and vineyards, sets the perfect stage for your unforgettable adventure. Enjoy an aperitif and dinner under the starry Tuscan sky, savoring exquisite local cuisine and wine, as you immerse yourselves in the timeless romance of Italy. Check-in in the afternoon if you wish relaxing and enjoying the pool.


  2. Day2 Drive the Colourful Landscapes of Siena with Overnight in Montalcino

    After Breakfast, hop into your vintage convertible and set out for the colorful landscapes of Siena.  A captivating drive through the colorful landscapes of Siena. Wind through charming medieval villages, traverse cypress-lined roads, and discover hidden gems along the way. Your journey culminates with an overnight stay in the picturesque town of Montalcino, renowned for its exceptional Brunello wines. Delight in an evening of wine tasting and gastronomic pleasures in this charming hilltop town.

  3. Day3 Driving Journey through the Idyllic Hills of Val d'Orcia and Pienza

    Wake up to the stunning views of Montalcino and prepare for a scenic drive through the idyllic hills of Val d’Orcia. This UNESCO World Heritage Site is a haven of natural beauty and tranquility. Your route leads you to the famous town of Pienza, known for its Renaissance architecture and delectable pecorino cheese. Explore the quaint streets hand in hand and create cherished memories against the backdrop of rolling hills and historic charm.

  4. Day4 Explore the “Chiantishire” with Private Tour and Wine Tasting

    Your journey continues as you drive through the enchanting landscapes of the ”Chiantishire.” Immerse yourselves in the heart of Tuscany’s wine country with a private tour of historic cellars. Learn about the art of winemaking and indulge in exclusive wine tastings, savoring the flavors of Chianti Classico. Immerse yourself in the rich wine culture of Tuscany, visit little towns and drive to the end of your adventure.


  5. Day5 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.

Hotels and Villas

As the sun sets, you’ll check into 4* or 5*carefully selected hotels with swimming pool, where evenings are yours to enjoy as you please. Explore the charming towns, savor romantic dinners at your own pace, or simply unwind in the tranquil Tuscan surroundings.


The tour package inclusions and exclusions at a glance.



if you don’t find it please shoot an email or whatsapp us

at the first hotel

If you wish we are happy to arrange transfers from Pisa, Bologna, Florence, Rome and Perugia main airports or from other destination you require.

Overall Rating


Package Confirmed Dates Trip Status Trip Status Price (PP) Excluding Flights Price (PP) Including Flights  
16 September 2024 - 20 September 2024
2 October 2024 - 6 October 2024
14 October 2024 - 18 October 2024
5 May 2025 - 9 May 2025
2 June 2025 - 6 June 2025
15 September 2025 - 19 September 2025
6 October 2025 - 10 October 2025
13 October 2025 - 17 October 2025