Between heritage towns, rural romance and culinary delights, experience Tuscany at its authentic best
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- Showcase such Tuscan highlights as Florence and Siena
- Head off the beaten track to the region’s medieval hilltop towns
- Indulge with Tuscany's world-leading food and wine
- End with a stay in a Tuscan castle
- Explore at your own pace with car hire included throughout
- 1 Night Florence
- 1 Night Lucca
- 1 Night Viareggio
- 1 Night Castellina in Chianti
- 1 Night Siena
- 2 Nights Chianti
Food & wine | History & culture | October holidays | Self-drive
This comprehensive fly-drive holiday showcases both Tuscany’s famed centrepieces and its lesser-known gems. Indeed, while you’ll take in Renaissance Florence, Pisa’s leaning icon and Cinque Terre’s clifftop fishing villages, you’ll also be treated to Chianti’s vineyard charm and the region’s hilltop medieval towns. And, with car hire included, you’ll enjoy life on the open road alongside stays in boutique properties and the chance to tuck in to the region's famed food and wine. It’s all rounded off in style with a two-night stay in Chianti castle where optional gourmet dining and poolside relaxation bring your holiday to a fittingly indulgent conclusion.
Day by day itinerary
Begin your trip with complimentary airport lounge access before flying to Pisa, where a short but scenic transfer brings you to Florence. Your charming 17th-century accommodation looks out onto one of the city’s prettiest basilicas. You’ll have some time to explore at your own pace today, perhaps taking in the Renaissance masterpieces of the world-famous Uffizi Gallery or losing yourself in Florence’s maze of cobbled streets. At every turn you’ll find beautiful churches, stern medieval vestiges and plaza-side cafés that spill onto the pavement.
Stay: Hotel Santa Maria Novella, Florence (Superior)
Start the day with a small group tour of Piazzale Michelangelo, Fiesole Hills and Accademia Gallery, complete with skip-the-line entry. Then, collect your car for the scenic drive to leafy Lucca. Once a republic capital, its 16th-century wealth survives today in gilded churches and terracotta-capped residences. It’s all watched over by dramatic Renaissance walls and even garden-capped towers. After some exploring, why not end the day with a dinner of regional specialities at a local osteria – we recommend La Buca di Sant'Antonio, where truffled cod mousse and Fiorentine steak are among the favourites.
Stay: San Luca Palace Hotel, Lucca (Superior)
Lucca, Pisa & Viareggio
Your first stop today is Pisa. Take a walk through the city to discover why it's so much more than its famed tower; there’s everything from fading merchants’ houses and Gothic churches to Romanesque piazzas and baptisteries resplendent in bright-white marble. Then carry on along the Tuscan Riviera to the hidden gem of Viareggio, where the vibrant beachfront is backed with huge hotels – your home for the night is Principe Piemonte, and we recommend borrowing a complimentary hotel bike for a ride along the promenade to watch the sunset over the Legurian Sea.
Stay: Grand Hotel Principe di Piemonte, Viareggio, Tuscan Riviera (Deluxe)
Viareggio, Volterra & Castellina in Chianti
Continue on to Volterra. Set on a plateau in the heart of the Tuscan countryside, its imposing walls, towers and churches command stunning views over undulating vineyards. And, hidden among its medieval heritage you’ll discover remnants of its Roman past, including a crumbling amphitheatre and millennia-old bathhouse. Continue on to Castellina in Chianti.
Stay: Tenuta di Ricavo. Castellina in Chianti (Superior)
Your first stop today is San Gimignano – a hilltop town encircled by 13th-century walls. But, among its Romanesque and Gothic charm, it’s the 14 towers that leave the strongest impression. Built as symbols of wealth by the San Gimignano aristocracy, they form a truly iconic skyline of medieval towers, including the stone Torre Grossa. The Duomo di San Gimignano is a 12th-century church with frescoes by Ghirlandaio in its Santa Fina Chapel. Then, it's on to Siena, heading into the city’s historic centre. Here, stepped streets map hilltop contours, bringing you between grand piazzas and the spectacular Italian Gothic cathedral.
Stay: Athena Hotel, Siena (Superior)
This morning, you’ll head south to have some time in the hidden Tuscan jewel of Pienza with town’s honey-stone heritage. Once a sleepy, hilltop village, it underwent a 15th-century transformation as Pope Pius II added churches, a palace and town hall. From Pienza, head north into Chianti for two nights at a Castle resort, where, between sipping wine on the terrace, enjoying gourmet dinners and lounging by the pool, you'll enjoy a truly relaxing end to your Tuscan journey.
Stay: Castello di Spaltenna (Superior)
While you’ll say goodbye to your Tuscan villa this morning, there’s one final treat in store. On a visit to a historic mill, you’ll enjoy a guided tour of the press before a light lunch and the chance to taste the olive oil. It’s a fitting end to your trip, before you head for Pisa and return your car hire at the airport for your flight home.
Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.
8-day tailor-made self-drive from £1,440 pp incl. flights
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