Discover Tuscany in Style

There’s no better way to explore Tuscany than in a Mercedes-Benz SL classic car. Step behind the wheel of your open-top, head-turning roadster and set off on an unforgettable adventure with the warm breeze in your hair. Your journey will take you through idyllic countryside, down quiet country roads and past lush vineyards and olive groves. You’ll explore medieval villages and castles, sample fine wine at a Chianti winery and soak up some culture in the historic city of Siena and the town of Pienza. Your accommodation will be an impressive county estate hotel, which overlooks Siena. This is Tuscan living at its finest!

Day 1: Chianti

Your trip starts from the enchanting Borgo Scopeto, a luxury boutique hotel that was once a nobleman’s estate. After a lavish lunch on the terrace as you enjoy the breathtaking views over Siena, it’s time to begin your journey through Tuscany in your gleaming vintage sports car. The route will take you past Chianti’s famed olive groves and vineyards, ancient castles, historic towns and grand palaces. You’ll of course have the chance to sample some fine Chianti wines at one of the world’s oldest vineyards.

Stay: Borgo Scopeto

Day 2: Pienza

Today, some of Tuscany’s most beautiful scenery and most awe-inspiring historic sites await. Enjoy a leisurely drive through the Crete Senesi, an area known for its unique lunar landscapes created by the gentle hills, solitary cypress trees, cornfields and blue-gray clay in the soil. Arrive in one of Italy’s artistic treasures, Pienza. This small town, designed by Pope Pius II as an “ideal Renaissance town”, is a UNESCO World Heritage Site. Here an expert guide will take you to an ancient castle and majestic Renaissance palaces, plus you’ll have the chance to wander Pienza’s winding cobbled streets and hidden alleys, saving time to stroll along the charming Corso Rossellino Boulevard. Afterwards, make your way back to your hotel along a road flanked with verdant vineyards, through the medieval hill town of Montepulciano. Spend a relaxing evening strolling through Siena’s old town before choosing to dine wherever you wish.

Stay: Borgo Scopeto

Day 3: Volterra

Today you will enjoy yet more breathtaking scenery on your drive, past imposing villas, secluded monasteries and medieval castles. You’ll come to the walled medieval hill town of San Gimignano before reaching Volterra, an Etruscan city famed for its alabaster carvings. Your guide will take you on a tour of the charming old town and to see Alabaster artists as they work in a studio. Your route back to the hotel takes you past world-renowned vineyards and the looming Tuscan Ore Mountains. Dinner will be at La Tinaia, where you can sample an array of local gastronomic delights.

Stay: Borgo Scopeto

Day 4: Siena

Spend the day soaking up the culture and atmosphere in the enchanting city of Siena, distinguished by its medieval brick buildings and home of the world-famous horse race, Palio di Siena, held in the Piazza del Campo. You’ll enjoy a guided tour of the city’s artistic and architectural masterpieces including the beautiful gothic cathedral made from marble and famed for its impressive floor panels designed by Siena’s leading artists. As your journey comes to an end, you will be chauffeur-driven to Florence Airport for your flight home, when you will say “arrivederci” to unforgettable Tuscany.


Duration Description Overnight
Day 1: Chianti Borgo Scopeto
Day 2: Pienza Borgo Scopeto
Day 3: Volterra Borgo Scopeto
Day 4: Siena



  • Nostalgic Mercedes-Benz SL (W 113 and R 107) classic car to drive yourself, including fully comprehensive insurance (EUR 500 excess) and petrol
  • Accommodation with daily breakfast
  • Transfers
  • 24 hour emergency contact
  • Activities mentioned in the itinerary
  • English speaking tour guide

Not Included

  • International and domestic airfare
  • Personal expenses
  • Visa fees and/or visa authorization
  • Tips and gratuities
  • Other expenses not mentioned on the itinerary
  • Travel insurance (please note that travel insurance is mandatory for all Lightfoot Travel holidays)


Borgo Scopeto Pienza Volterra Siena

From USD 2,785 per person based on two guests travelling

Notes on our prices

  • This price guide provides you with a broad indication of how much to budget for your holiday.
  • Prices are generally based on two people travelling together (unless stated otherwise) on a shared room basis.
  • Prices can fluctuate depending on season, standard of accommodation, excursions selected (private versus shared) etc.
  • This basic structure works very nicely, but don’t forget that Lightfoot Travel can provide a range of experiences and we tailor-make each itinerary based on your travel requirements. Get in touch to start planning your perfect trip with your own travel consultant.