Tuscany 5-Day Vintage Convertible Car Tour


Indulge in the romance of Tuscany with our 5-day, 4-night getaway that rekindles the spirit of the “dolce vita.” This enchanting journey takes you on a guided tour through the heart of Tuscany, where you’ll traverse the rolling hills of Chianti, the picturesque Val d’Orcia, and the captivating Sienese countryside in a vintage 2-seater convertible.

Our small group tour, limited to just 3-4 couples, ensures an intimate and personalized experience. Each couple has their own classic car, following the lead vehicle through this breathtaking landscape. Your daily itinerary is expertly curated, featuring scenic stops, guided tours, and delightful lunches at local gems.

As the sun sets, you’ll check into carefully selected hotels, 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.

This romantic escape is a celebration of love, beauty, and the Italian way of life. Immerse yourselves in the “dolce vita” as you create lasting memories against the stunning backdrop of Tuscany’s rolling hills and vineyards. Book your dream getaway today and embark on a journey that will forever hold a special place in your heart.

You can decide to pay in full at time of booking, or secure your booking paying a 50% booking deposit. Balance is due 30 days before tour departure by credit card/wire transfer. 

Instead if you book this tour closer than 30 days to the departure date is required full payment.

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Experience Overview

Experience the essence of “La Dolce Vita” with our Romantic Tuscany Getaway, a 5-day, 4-night journey that will sweep you off your feet. Revel in the timeless allure of Tuscany as you embark on a 3-day vintage convertible car tour adventure through picturesque landscapes, complemented by exquisite dining, wine tastings, and country accommodations.

Day 1: Al Fresco Welcome Dinner at Villa Sabolini, Casole d’Elsa As you step into the heart of Tuscany, your romantic journey begins with an al fresco welcome dinner at the enchanting Villa Sabolini in Casole d’Elsa. 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.

Day 2: 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.

Day 3: 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.

Day 4: 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.

Day 5: 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.

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.

The experience package inclusions and exclusions at a glance
What is included in this experience? Items that are included in the cost of experience price.
  • Overnight stay in Montalcino and Chianti area.
  • Driving journeys through Siena country side, Chianti Wine Region and Val d’Orcia.
  • Visits of charming country villages
  • in depth visit of Siena, with local expert guide
  • Private group tour and wine tasting in the Chianti region.
  • 3 smal group luncheons – all together
  • Farewell breakfast to conclude the journey.
  • Local Tour Manager leading the driving tour
  • Small Group Travel
  • All Taxes and Vat.

PN: Price is intended for a couple/2 Participant
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.

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