Alexander+Roberts

Rome to Tuscany - Privately Guided Italy

Rome to Tuscany – Privately Guided Italy
Highlighted by five UNESCO World Heritage Sites, this in-depth Original Journey is a distinctive combination of Italy’s sophisticated urban appeal, its pastoral landscapes, and charming medieval hilltop towns. In short, it’s all that we love about Italy enhanced by our engaging professional guides, terrific deluxe hotels and signature Private Touring services.

05/15/2025 through 12/18/2026
05/01/2025 through 12/31/2026

Day 1 Often called the Eternal City, Rome stands alone as Italy's most visited destination. The third most populated city in the European Union, Rome boasts ancient sites, yet has a modern flair — an exhilarating mix of the Old World and the new.

Rome's must-see attractions include the Colosseum, Trevi Fountain, Pantheon, and St. Peter's Basilica. Of course, within the city limits of Rome lies an independent country: Vatican City, the Roman Catholic Church headquarters and the only current example of a country inside a city.

With its Renaissance architecture, ancient ruins, and works by Michelangelo, Rome is a vibrant destination offering spectacular examples of human achievement. Visitors wandering through this glorious city have so much to discover!
Day 2 Often called the Eternal City, Rome stands alone as Italy's most visited destination. The third most populated city in the European Union, Rome boasts ancient sites, yet has a modern flair — an exhilarating mix of the Old World and the new.

Rome's must-see attractions include the Colosseum, Trevi Fountain, Pantheon, and St. Peter's Basilica. Of course, within the city limits of Rome lies an independent country: Vatican City, the Roman Catholic Church headquarters and the only current example of a country inside a city.

With its Renaissance architecture, ancient ruins, and works by Michelangelo, Rome is a vibrant destination offering spectacular examples of human achievement. Visitors wandering through this glorious city have so much to discover!
Day 3
Day 4
Day 5 In the walled city of Siena we stand firmly planted in the Middle Ages. Siena preserved its original character more markedly than any other city in Italy.
Day 6

Tuscany, Italy, is a region where the essence of Italy's beauty, history, and culture is captured in its rolling hills, timeless villages, and world-class art. Famous for its postcard-perfect landscapes, Tuscany is where cypress-lined roads lead to centuries-old hilltop towns like Montepulciano and Montalcino, which are steeped in history and offer some of Italy's finest wines, including the renowned Brunello di Montalcino. Tuscany is a treasure trove for lovers of art and architecture, boasting some of the most important works from the Renaissance period. The city of Florence, Tuscany’s capital, is a UNESCO World Heritage Site and home to the Uffizi Gallery, where you can witness masterpieces by Michelangelo, Botticelli, and Leonardo da Vinci. A visit to the Cathedral of Santa Maria del Fiore with its iconic terracotta dome is essential, offering breathtaking views of the city and its surrounding countryside.

For those drawn to medieval charm, the walled city of Siena is a must-see. Famous for the Palio, a thrilling horse race held twice a year in its central Piazza del Campo, Siena's medieval streets unfold into a captivating blend of Gothic architecture and Tuscan culture. Visit the Siena Cathedral, a black-and-white striped marvel of Romanesque-Gothic architecture, which houses works by Donatello and Michelangelo. Siena also offers an authentic Tuscan culinary experience with local dishes such as pici pasta and ribollita soup, paired with robust local wines like Chianti Classico.

No trip to Tuscany would be complete without exploring its breathtaking countryside, especially the Val d'Orcia, another UNESCO World Heritage site. Known for its undulating hills, vineyards, and olive groves, the Val d'Orcia offers picture-perfect scenery that has inspired painters for centuries. Towns like Pienza, designed by Pope Pius II as the “ideal Renaissance city,” offer intimate experiences of Tuscan life. Wander through charming cobblestone streets, sample pecorino cheese, and gaze at the landscapes that stretch as far as the eye can see.

Fun fact: Tuscany is not just about history and art; it's also the birthplace of one of Italy's most iconic cultural treasures—the gelato. The first gelato is believed to have been created in the 16th century by Bernardo Buontalenti, a native of Florence, who impressed the Medici court with his delicious, creamy invention. Today, Tuscany continues to be a fantastic place to savor artisanal gelato, making it a perfect stop for food lovers looking to indulge in authentic Italian flavors.


Day 7 Florence (Firenze) is a compact city, but densely packed with spectacular art and architecture everywhere you look. The city center itself is a UNESCO World Heritage Site.

Birthplace of the Renaissance as well as Italy's fashion industry, Florence is imbued with an air of history and sophistication. Visitors are sure to be enchanted with the Florentine way of life, from the sensational Tuscan cuisine to the Michelangelo masterpieces. Art and food lovers will find much to embrace here.

Looming over Florence is the Duomo, a red terracotta dome that is part of the Cathedral of Santa Maria del Fiore. Bellissima!
Day 8 Florence (Firenze) is a compact city, but densely packed with spectacular art and architecture everywhere you look. The city center itself is a UNESCO World Heritage Site.

Birthplace of the Renaissance as well as Italy's fashion industry, Florence is imbued with an air of history and sophistication. Visitors are sure to be enchanted with the Florentine way of life, from the sensational Tuscan cuisine to the Michelangelo masterpieces. Art and food lovers will find much to embrace here.

Looming over Florence is the Duomo, a red terracotta dome that is part of the Cathedral of Santa Maria del Fiore. Bellissima!
Day 9 Florence (Firenze) is a compact city, but densely packed with spectacular art and architecture everywhere you look. The city center itself is a UNESCO World Heritage Site.

Birthplace of the Renaissance as well as Italy's fashion industry, Florence is imbued with an air of history and sophistication. Visitors are sure to be enchanted with the Florentine way of life, from the sensational Tuscan cuisine to the Michelangelo masterpieces. Art and food lovers will find much to embrace here.

Looming over Florence is the Duomo, a red terracotta dome that is part of the Cathedral of Santa Maria del Fiore. Bellissima!
Day 10

05/01/25 - 06/30/25

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07/01/25 - 08/31/25

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09/01/25 - 10/31/25

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11/01/25 - 11/30/25

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12/01/25 - 12/19/25

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12/20/25 - 12/31/25

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01/01/26 - 02/28/26

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03/01/26 - 03/23/26

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03/24/26 - 04/23/26

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04/24/26 - 07/15/26

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07/16/26 - 08/30/26

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08/31/26 - 10/30/26

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10/31/26 - 12/22/26

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12/23/26 - 12/31/26

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Please note that 2025 is a Holy Jubilee Year in Rome please <a for more details.</u></a><br>

All prices are per person and may vary by day of week and during holidays and trade shows.
This itinerary offers a choice of optional sightseeing tours, please select your included sightseeing tour choices at least 90 days before your travel start date. Availability of included sightseeing tours may be affected by holidays, museum closures and seasonally-adjusted schedules.
Prices subject to availability and change without notice. Some restrictions may apply.

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