We are open today until 6:30 pm. Call 020 7590 0796
Siena, Italy

Tuscany, Umbria & Amalfi self-drive

10-day tailor-made self-drive from £2,195 pp incl. flights


Short description

Soak up the cultural heritage, natural beauty and tantalising cuisine of three Italian gems


  • Pair fine wines and gourmet food in the Chianti region
  • Call into ancient temples and Roman theatres as you drive through Tuscany's rural heartland
  • Explore the cobbled lanes and medieval piazzas of Orvieto in rural Umbria
  • Explore the Amalfi Coast, gateway to glamour of Capri and the ruins of Pompeii

In Brief

  • 3 Nights San Gimignano
  • 2 Nights Cortona
  • 1 Night Todi
  • 3 Nights Sorrento


Recommended for:
Food & wine | History & culture | Self-drive

Famous for its stunning scenery, cultural heritage and picturesque cities and towns, Tuscany is the ideal starting point for a self-drive holiday. Soak up the sights including the famous tower of Pisa, before spending three nights in the beautiful, walled medieval hill town of San Gimignano. Continue your journey south of Italy to the Amalfi Coast, well-known for its winning combination of cathedrals, grottos, fine cuisine and of course, the natural beauty of the coastline.

Day by day itinerary

Day 1

Fly to Pisa, and upon arrival collect your hire car. Begin the journey to San Gimignano, located approximately 90km from Pisa, stopping off at the Leaning Tower of Pisa first. Continue the short drive, arriving at the beautiful hill town of San Gimignano west of Siena. San Gimignano is the perfect base to explore the wine region of Chianti, and the rest of the day is at your leisure to do so.

Stay: Hotel La Cisterna, San Gimignano (Superior)

Day 2
San Gimignano - Volterra – Colle Val d’Elsa

Head to Volterra, located on a steep hill and founded by the Etruscans 2,700 years ago, this precious town is well known for the production of alabaster. While here, visit the majestic, protective walls built centuries ago, the city gates, remains of ancient temples, the Medicean Fortress and the Roman theatre. If not, drive to Colle Val d'Elsa, famed in ancient times for the production of wool, paper and ceramics, known today as the largest producers of fine glass and crystal in Italy. If you have chosen to venture to Colle, be sure not to miss Monteriggioni, a tiny fortified village located 30 minutes away.

Stay: Hotel La Cisterna, San Gimignano (Superior)

Meals: B

Day 3
San Gimignano

Spend the day at your leisure, exploring and discovering the highlights of San Gimignano and its neighbours. Perhaps begin in the Piazza, admiring the town hall and the town museums, home to a prestigious collection of frescoes and important works of art, dating back to the 13th and 17th centuries. Spend the afternoon climbing the town's highest tower, basking in the view from the Torre Grossa. End your last day in Sam Gimignano with either an evening of wine tasting, or visit open air museum Certaldo Alto, home of Giovanni Boccaccio, author of the Decameron.

Stay: Hotel La Cisterna, San Gimignano (Superior)

Meals: B

Days 4-5
San Gimignano – Siena – Cortona

After an early breakfast, depart from San Gimignano and begin the drive to Siena. Upon arrival, you will be met by an official guide for a three hour guided walking tour, visiting some of the attractions of one of Tuscany's most beautiful cities, including Piazza del Campo, Palazzo Pubblico, the Duomo and the Baptistery. Spend the afternoon as you wish, before continuing the drive to near Cortona for a two-night stay.  Here, the main attraction is the wine, and a visit to a local vineyard, and the Tuscan menu using the best local ingredients.

Stay: Relais La Corte Dei Papi, Tuscany (Deluxe)

Meals: B

Day 6
Cortona - Pienza - Todi

This morning, check out of the hotel after breakfast and set off for Pienza, the birthplace of Pope Pius II. A legacy of Pius, the small village was transformed into a Renaissance city building, of palaces, houses and squares. After lunch, drive south to the outskirts of Todi for an overnight stay.

Stay: Fonte Cesia, Todi (Superior)

Meals: B

Days 7-9

After breakfast, take a wander around the Orvieto Cathedral, bult in the 14th century the Gothic cathedral is one of Italy's most celebrated. Begin the drive to Castellamarem a small commune on route to Sorrento, passing through Rome and Naples along the way. The next day is free to explore Sorrento and its Amalfi Coast surrounds, perhaps driving the iconic Blue Ribbon Road past pretty lemon groves and cliff-hugging villages, taking the ferry across to glamorous Capri, or heading for Mt. Vesuvius and the ruins of Pompeii. Return your hire car on day nine.

Stay: Grand Hotel La Favorita, Sorrento (Deluxe)

Meals: B

Day 10

After a leisurely breakfast, an included transfer will bring you to Naples Airport in time 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 Deluxe

10-day tailor-made self-drive
from £2,195 pp incl. flights

Superior / Deluxe

Apr / Oct

from £2,195 pp. incl. flights

May - Sep

from £2,940 pp. incl. flights

Valid for travel:  Apr - Oct


  • Return flights into Pisa and out of Naples
  • 9 nights Superior accommodation BB
  • 7 days economy car hire
  • 3 hour private walking tour in Siena
  • Airport transfer Sorrento to Naples airport on day 10

A one way drop-off fee between Pisa and Sorrento is payable locally of approximately Euro110.00

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.

Meet our experts

Speak to a tailor-made specialist on 020 7590 0796

Meet the team

Why book with Wexas Travel?

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.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

Expert advice & support

Visit us in our London office

Let our travel specialists curate the perfect holiday:

  • Inspirational ideas based on experience
  • Established for over 50 years
  • Tailor a holiday to your precise requirements
  • Personalised quotes and documentation

Every step of the way

Every step of the way

Our services are with you from start to finish:

  • Dedicated personal consultants
  • Free airport lounges on qualifying bookings
  • Care and guidance pre, post and during holiday
  • Full financial security: ABTA & ATOL protected