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Tuscany and Hill Towns Self-Drive Home > Italy > Tuscany and Hill Towns Self-Drive
Florence, the capital of Tuscany, is one of Italy`s most atmospheric and pleasant, retaining a strong resemblance to the small late-medieval center that contributed so much to the cultural and political development of Europe.

Siena is a city of brick, where urban development all but ceased after the great plague of the 14th century, busy as it was defending itself.

Arezzo is a beautiful town that sits atop a hill at the crossroads of four valleys: Val Tiberina, Casentino, Valdarno and Valdichiana.

One of the oldest hill towns in Tuscany, surrounded by 3,000 year old Etruscan walls, Cortona retains much of its history through its architecture, layers of history built upon the Etruscan core.

Castellina in Chianti, on a hill at the crossroads of the Arbia, Elsa and Pesa valleys, is set along the Chiantigiana road that connects Florence to Siena.

Gaiole in Chianti is an important city within the Chianti Classico region, located along the river Massellone and on the road connecting Chianti to Valdarno.

Lucca is located on a plain at the foot of the Apuan Alps and is less than half an hour from the Tuscan coast.

Montecatini Terme is heaven for those who love spa treatments! The curative powers of the hot springs and steaming vaporous caverns of the Valdinevole have been renowned for centuries.

Montepulciano is an interesting walled hill town in Tuscany, built on a sloping and narrow limestone ridge in the heart of the Vino Nobile wine growing area and commanding the southeast part of Tuscany near the Umbrian border.

Best known for the world famous Leaning Tower, yet there are other architectural and artistic marvels of this beautiful city.

Pienza, in the Val d`Orcia in Tuscany, between the towns of Montepulciano and Montalcino, is the `touchstone of Renaissance urbanism.`

Although the area around Poggibonsi was already settled in the Neolithic age, the first traces of civilization dates from Etruscan-Roman age, attested by a series of necropolises and by place names such as `Talciona` or `Marturi` (from the Etruscan name of Mars).

Located up on a hill, covered with woods and extensive vineyards between the valleys of Arbia and Pesa, Radda in Chianti is a beautiful medieval town enclosed in large defensive walls.

San Gimignano is a small walled medieval hill town in the Tuscany, known as the `City of Beautiful Towers`, which has preserved its medieval appearance more completely than any other town in Tuscany.

Most Popular self-drive Itineraries:
9 nts from $1,319*
Focus your visit to Italy in wonderful Tuscany! Visit artistic Florence, then pick up your car and spend some leisurely days staying in Lucca, San Gimignano and Siena to be able to experience all the different aspects of this charming region. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
  • Flight into Florence and out of Florence
  • Hotel for 2 nights in Florence
  • Rent a car for 6 days
  • Hotel for 2 nights in Lucca
  • Hotel for 2 nights in San Gimignano
  • Hotel for 2 nights in Siena
  • Hotel for 1 night in Florence
  • Daily breakfast (if stated in hotel info)
  • Hotel taxes
Customize it!
Related destinations:

Florence (165)   Lucca (9)   San Gimignano (5)   Siena (25)  
Italy (346)
For more choices, combine cities found in this itinerary:
Florence Lucca San Gimignano
More Self-Drive Itineraries
9 nts from $1,319

9 nts from $1,319

9 nts from $1,319

9 nts from $2,263

9 nts from $1,319
Customize Suggested Itineraries
Combine cities
Castellina in Chianti  
Gaiole in Chianti  
Montecatini Terme  
Radda in Chianti  
San Gimignano  
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Trips Taken - Tuscany and Hill Towns
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* Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.
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