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Tuscan Highlights (Florence - Siena - San Gimignano - Self Drive)
2 Customer Feedbacks
7 to 10+ Nigths from $1,223*
This sample price: priced within the past 7 days for arrival on 7/21/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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2 Customer Feedbacks Our trip was lovely in every way. Each hotel was beautiful in a unique way, clean, quiet, ... more
This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
A unique trip to Italy's Tuscany Region by car! . Discover Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and from there, with Rental Car, main cities in Tuscany, like Siena (famous for its cuisine, art, museums, medieval cityscape and the Palio, a horse race held twice a year in Piazza del Campo) and San Gimignano (famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses). Drive back to Florence to drop off the car and finisht this trip with one last night stay. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
This 7 night sample itinerary includes:
  • Flight into and out of Florence
  • Hotel for 2 nights in Florence
  • Rental Car for 6 days
  • Hotel for 2 nights in Siena
  • Hotel for 2 nights in San Gimignano
  • Hotel for 1 night in Florence

  • Driving Time
    Florence - Siena: 1 hr. 10 mins. approx.
    Siena - San Gimignano: 1 hr. approx.
    San Gimignano - Florence: 1 hr. 15 mins. approx.

Price history for this itinerary (past 7 days):
From Pensacola PNS (FL), US for 12 nights
3775.97 * incl.tax
Related Itineraries:
Related Cities:
Florence (223)     Siena (26)     San Gimignano (10)     Southern Tuscany (13)    
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With Int'l Flight     Without Int'l Flight
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Destination
Arrival date
Stay
1. Florence
  284 hotels
2. Siena
   (65 hotels)
3. San Gimignano
   (35 hotels)
4. Florence
   (284 hotels)
Guest:
Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
2 nights in Florence

The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.



2 nights in Siena

The beautiful town of Siena is the largest of hill towns that are scattered among Tuscany. The city is famous for its large square, Piazza Del Campo, winding medieval alleyways, and the Palio, a historic horse race that takes place twice during the summer months. Today, Siena continues to maintain a distinctively medieval atmosphere and is a great place to discover Tuscany at its medieval best, with numerous gothic palaces, pastry shops and unequaled altarpieces.

Visit and discover the Cathedral of Santa Maria Assunta; Piazza del Campo; Palazzo Pubblico; Torre del Mangia; Biblioteca Piccolomini; Siena National Gallery; Church of San Domenico; Piazza Salimbeni; Porta Pispini; Siena Civic Museum and so much more.



2 nights in San Gimignano

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. It stands on the site of a small Etruscan settlement dating to second BC. Its history begins around the Tenth Century. Truly a little gem, it has been declared a World Heritage Site by UNESCO. Walking through the Old City means plunging into the Middle Ages and getting a taste of what the city must have been like more than seven hundred years ago.

Visit and explore the amazing Terme di Petriolo, Volterra, Colle Val d'Elsa, San Gimignano, Montaione, Pienza, Bagno Vignoni and so much more.



1 nights in Florence

The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.



Book This Package
Flexible Itinerary
Florence
Day 1
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1356 Things to do
Day 2
Overnight in Florence   284 hotels offered
Optional   1356 Things to do
Day 3
Departing from Florence
Transportation to next city by: Regional Air
Siena
Day 3
Arrive to Siena
Overnight in Siena   65 hotels offered
Optional   97 Things to do
Day 4
Overnight in Siena   65 hotels offered
Optional   97 Things to do
Day 5
Departing from Siena
Transportation to next city by: Regional Air
San Gimignano
Day 5
Arrive to San Gimignano
Overnight in San Gimignano   35 hotels offered
Optional   57 Things to do
Day 6
Overnight in San Gimignano   35 hotels offered
Optional   57 Things to do
Day 7
Departing from San Gimignano
Transportation to next city by: Regional Air
Florence
Day 7
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1356 Things to do
Day 8
Departing from Florence
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Florence Hotels (284 total)
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Siena Hotels (65 total)
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San Gimignano Hotels (35 total)
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Tours in Florence (1356 total)
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Tours in Siena (97 total)
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Tours in San Gimignano (57 total)
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Italy

For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
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Tuscan Highlights (Florence - Siena - San Gimignano - Self Drive)
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Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.
Siena
The beautiful town of Siena is the largest of hill towns that are scattered among Tuscany. The city is famous for its large square, Piazza Del Campo, winding medieval alleyways, and the Palio, a historic horse race that takes place twice during the summer months. Today, Siena continues to maintain a distinctively medieval atmosphere and is a great place to discover Tuscany at its medieval best, with numerous gothic palaces, pastry shops and unequaled altarpieces.

Visit and discover the Cathedral of Santa Maria Assunta; Piazza del Campo; Palazzo Pubblico; Torre del Mangia; Biblioteca Piccolomini; Siena National Gallery; Church of San Domenico; Piazza Salimbeni; Porta Pispini; Siena Civic Museum and so much more.
San Gimignano
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. It stands on the site of a small Etruscan settlement dating to second BC. Its history begins around the Tenth Century. Truly a little gem, it has been declared a World Heritage Site by UNESCO. Walking through the Old City means plunging into the Middle Ages and getting a taste of what the city must have been like more than seven hundred years ago.

Visit and explore the amazing Terme di Petriolo, Volterra, Colle Val d'Elsa, San Gimignano, Montaione, Pienza, Bagno Vignoni and so much more.
Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.

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