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Arezzo
Arezzo, formerly a military fort on the Via Cassia, is one of the most historic cities in Italy. The illustrious collection of frescos in ancient cathedrals, the monthly antiques fair and the annual jousting match held in the main square...
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Ballooning over Tuscany
There are a handful of spots on Earth where ballooning is not a gimmick but a must (Cappadoccia, East Africa and Myanmar’s Bagan also figure on this list). Indagare members can contact our Bookings Team for help organizing an early...
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Castiglion del Bosco Cooking Classes
The latest from the Ferragamo family, this hideaway close to Montalcino has a golf course, stables and impeccable amenities. During the harvest, guests can sign up for a day in the vineyards, helping pick the grapes and ending with an...
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Chianti
Situated between Florence and Siena, this wine-growing region is one of the world’s most famous. There are a number of attractive hilltop towns that can be visited in a day of touring, including Greve in Chianti, Castellina in Chianti, Gaiole...
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Cortona
Immortalized by Frances Mayes’s novel and film adaptation Under the Tuscan Sun, Cortona has come to be a stand-in for the life-changing, picturesque hilltop Italian town. This small city in the Arezzo province offers an unparalleled vantage point for the...
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Crete Senesi
After lunch in Siena, explore the remarkable Crete Senesi, a 300-square-mile area south of Siena whose winding country roads afford breathtaking vistas of hills and woodland. It is best known for its ocher soil, made popular by Renaissance painters, as...
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Custom Wine Itineraries
Much more so than compact Napa and Sonoma, Tuscany can overwhelm with its sheer number of wineries and vineyards. Some are large businesses with set-up tasting rooms and export service. But the ones to know are those normally closed to...
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Il Falconiere Cooking School
The one-starred Michelin chef of Il Falconiere, a lovely retreat near Cortona, hosts an excellent cooking school, with courses offered from one day, three days or six days.
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Indagare Tours: Boating from Porto Ercole to Porto Giglio
Explore the Tuscan coast from the water with a full day boat trip on a chartered boat with an English-speaking captain. Make a visit to the island of Giglio, where you can explore its charming village lanes, church, medieval castle...
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Indagare Tours: Day trip to Orvieto and Civita di Bagnoregio
Take a car and driver to explore two of the most scenic spots in the area. Your English-speaking guide will guide you through the streets and history of clifftop Orvieto with its wonderful historical center, duomo and archaeological museum. After...
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Indagare Tours: Pisa and Lucca Tour
Enjoy a full day tour of two of the region’s prettiest cities with an English-speaking guide. You can start with a visit to the famous leaning tower and stop at Gothic churches and scenic lookouts on the way to Lucca...
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Indagare Tours: Private Cooking Class
Want to learn the secrets of Italian cooking? Whether you fantasize about preparing pizza, pasta, risotto or osso bucco, you can do so in a fabulous school environment where a class is tailored to you and then you get to...
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Indagare Tours: Shopping Day
Have an English-speaking driver pick you up and take you to the Chianti wine region for a tour of vineyards, charming towns and a lovely lunch before taking you to the designer outlet mall for an afternoon of shopping Gucci,...
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Indagare Tours: Siena
Take a tailored tour of Siena. Whether you want to focus on history and walking or special access, which can mean being treated to tales of intrigue about the aristocratic families of the region and then being invited into the...
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Indagare Tours: Truffle Hunt and Cooking Class
Combine the fun of hunting for truffles with a truffle expert with a cooking class in an Italian kitchen, in which you will learn how to prepare the bounty you have hunted. You will hunt the truffles with a local...
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Indagare Tours: Tuscany’s Wine Region
Have an English-speaking driver pick you up in a Mercedes for a tour of top vineyards in the region. You will visit Montalcino, the capital of the Brunello wine region, tour its medieval town, head to the Sant’Antimo abbey, then...
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Indagare Tours: Vespa Tour in Chianti
Does your Italian fantasy include riding on a Vespa? One of the best ways to enjoy the Chianti region is by Italian motorbike. We can arrange a tour that has you wending your past vineyards and olive groves and includes...
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Montalcino
A medieval city-on-a-hill, Montalcino affords astonishing scenery and a glimpse into a region relatively unchanged for the past 500 years. It also offers unparalleled varietals for wine enthusiasts. As home to the illustrious Brunello wine, Montalcino can safely be described...
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Montepulciano
As the highest of Tuscany’s “hill towns,” Montepulciano, with its car-free, winding streets, encapsulates the long-standing history and culture of central Italy at its finest. Montepulciano offers the same abundance of wineries endemic to the region, and the surrounding Vino...
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Monticchiello
There’s not a ton to see and do here but Monticchiello is one of Tuscany’s most ridiculously picturesque walled villages, close to the Renaissance town of Pienza. It’s also become a foodie destination thanks to restaurant La Porta, which has...
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Pienza
Pienza’s burnt brick–and–terracotta village was designed by Pope Pius II to be the ideal Renaissance city. Perched on a hilltop overlooking the picturesque Tuscan landscape, the quaint town is home to several excellent restaurants, a handful of authentic shops and...
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San Gimignano
Many coastal-bound visitors kick off their itineraries in this hilltop town, a little less than an hour’s drive northwest of Siena, whose medieval towers and walls have been beautifully preserved. Spend the morning marveling at the city’s fourteen remaining towers,...
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Sansepolcro
Art lovers should make a note to visit the hometown of Piero della Francesca, one of the early Renaissance most acclaimed artists. The Museu Civico features his Resurrection of Christ, once described as the “greatest painting in the world” by...
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Sant’Antimo Abbey
The Romanesque edifice of Sant’Antimo abbey surrounded by the rolling green hills and olives groves of Tuscany is breathtakingly picturesque. The oldest in the region – construction began before the 11th century and drew from French influence – Sant’Antimo was...
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Siena
One of seven UNESCO World Heritage Sites in the region, Siena’s historic center sees a significant amount of tourism, thanks to its medieval architecture, ornate monuments and biannual Palio horse race. A day or two is all you need to appreciate...
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Volterra
The walled city Volterra is one of the twelve Etruscan power centers and most famous for its soaring clock tower in the Palazzo dei Priori, as well as for its locally mined alabaster. It contains numerous alabaster studios and shops....
Tuscany

Courtesy of Locande dell'Amorosa
The region of Tuscany is actually a massive place, stretching from the Tyrrhenian Sea all the way to Umbria in the east. The Chianti region is located between Florence and Siena; south of Siena lies the famously scenic Val d’Orcia. Many travelers plan road trips through this region, so choosing where to be based is key. Indagare members can contact our Bookings Team for help with trip planning, including customized recommendations and itineraries.