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Siena, Tuscany, Italy

Best of Tuscany

11-day tailor-made self-drive from £1,970 pp incl. flights


Short description

Between heritage towns, rural romance and culinary delights, experience Tuscany at its authentic best


  • 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

In Brief

  • 2 Nights Florence
  • 1 Night Lucca
  • 2 Nights Forte dei Marmi
  • 1 Night Colle di Val d'Elsa
  • 1 Night Siena
  • 1 Night Montepulciano
  • 2 Nights Radda in Chianti


Recommended for:
Best of holidays | 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, and Pisa’s leaning icon, 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. 

Day by day itinerary

Days 1-2
UK to Florence

Begin your trip with complimentary airport lounge access before flying to Florence, where a short but scenic transfer brings you to your central hotel. 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 L'Orologio Florence (Superior)

Meals: B

Day 3

This morning after breakfast 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)

Meals: B

Days 4-5
Pisa & Forte dei Marmi

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 Forte dei Marmi, where the vibrant beachfront is backed with restaurants and hotels – your home for the next two nights is Franceschi Villa Mimosa where you can walk along the nearby promenade to watch the sunset over the Legurian Sea.

Stay: Hotel Franceschi Villa Mimosa (Superior) 

Meals: B

Day 6
Volterra, San Gimignano and Colle di Val D'Esta

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. Then continue to 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. Finish the day in Colle di Val D'Este, known for its crystal glass production, but it also offering great views of Tuscany, a medieval atmosphere, nice restaurants and a beautiful Duomo.

Stay: Palazzo San Lorenzo, Colle di Val D'Elsa (Superior)

Meals: B

Day 7

Then, it's on to Siena, leaving your car and heading into the city’s historic centre on foot. Here, stepped streets map hilltop contours, bringing you between grand piazzas and the spectacular Italian Gothic cathedral. Siena's heart is its central piazza known as Il Campo, known worldwide for the famous Palio run here, a horse race run around the piazza two times every summer. 

Stay: Athena Hotel, Siena (Superior)

Meals: B

Day 8

After breakfast, make the short drive to Montepulciano, standing high atop a hill in southern Tuscany, a medieval town of rare beauty, full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners, boasting panoramas over the Val d'Orcia and Val di Chiana valleys. We recommend sampling one of Tuscany's most renowned red wines Nobile di Montepulciano whilst exploring the region and at your accommodation for the night surrounded by vineyards.

Stay: Borgo Tre Rose, Montepulciano (Superior)

Meals: B

Days 9-10
Pienza and Chianti

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:  Palazzo Leopoldo, Radda in Chianti (Superior)

Meals: B

Day 11
Chianti to Florence to UK

While you’ll say goodbye to your Tuscan villa this morning, it’s a fitting end to your trip, before you head for Florence and return your car hire at the airport for your flight home.

Meals: B



Any element of this itinerary can be adjusted to suit your needs. Just contact us to find out more.

Accommodation rating: Superior

11-day tailor-made self-drive
from £1,970 pp incl. flights


Apr / May / Oct

from £1,970 pp. incl. flights

Jun / Jul / Aug / Sep

from £2,365 pp. incl. flights

Valid for travel: April to October 


  • Complimentary UK departure airport lounge access
  • Return flights from UK to Florence
  • Private airport arrival transfer in Florence
  • 10 nights accommodation on a BB basis
  • 9 days car hire (pickup on day 3)

Itinerary not valid during Siena Il Palio 29 Jun - 02 Jul / 13 Aug - 16 Aug)

Terms & Conditions

Prices are per person based on two people sharing a twin/double room; prices are subject to availability and possible change; normal booking conditions apply.

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At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0796 to discuss how we can tailor your holiday.

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