Centered around Florence and encompassing such storied towns as Siena, Montepulciano and Arezzo, Tuscany is one of Italy’s most fabled regions, known for its gorgeous countryside, vineyards, old-world charm and coastline.
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
An ideal Tuscany itinerary combines outings with more relaxed activities all while based at Indagare Adored properties. Here is just one example of what our destination specialists can create for you.
Upon arrival in Tuscany, ease into the spirit of the region with a private cooking lesson and learn how to make homemade pasta, sauces and various other Tuscan specialties. Another favorite activity in Tuscany is setting off on a bike or horseback ride, through the forests, on winding lanes and along fields, which, depending on the season, might be bursting with sunflowers. Get a recommendation for a winery to visit en route. Our favorite hotels in Tuscany have excellent spas and feature treatments utilizing local beauty products.
Indagare can arrange special, insider experiences ranging from making your own olive oil or going truffle hunting to visiting a town featured in many movie sets and, of course, wine tasting to your heart’s content.
Tuscany is bursting with tiny towns to explore on half-day or full-day trips from your hotel. Favorite locales include Cortona, the setting for Under the Tuscan Sun, Montepulciano and Montalcino, wine-making meccas, Pienza, a fairytale-like walled city and the historic Siena, home to the twice yearly palio horse race.
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special perks, including upgrades, early check-in, spa credits, and more. Look for the Indagare Plus logo in the reviews.
At a Glance Take an Italian agricultural estate in Tuscany, complete with a winery and a historic village; add plush lodgings; and then pile on amenities—golf, tennis, spa, pool, fitness center. The result: Castiglion del Bosco. In 2003, Massimo Ferragamo...
Centrally located in the wine-heavy Montalcino area, the borgo of this castello is a great find for foodies who come for a meal and want to spend the night.
A five-star Tuscan resort managed by Belmond, Castello di Casole has a spa, vineyards, three restaurants, a bar and an epic infinity pool. Overall, the biggest criticism of the property has been that it feels somewhat compounded, as if it’s not...
This painstakingly restored Borgo near Siena has upped the luxury ante for the area.
The hilltop Monteverdi is a charming property with 12 rooms and three villas that are dotted throughout the small, 14th-century village of Castiglioncello del Trinoro.
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...
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...
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...
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...
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...
Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.
The travel landscape is always evolving—even when there isn’t a global pandemic. But the last two years have made it painfully clear just how unpredictable the world—and how we explore it—can be. Just this week, the Omicron variant has made...
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...
As 2022 comes to a close, Indagare's most-booked properties of the year reflect what many of us have desired for several years—a grandiose return to our favorite destinations (our homes-away-from-home, if you will). International travel is back, and Indagare members...
Whether you are setting off on an adventure in a new relationship or just looking to indulge in some well-deserved rest, one-on-one time and relaxation with your partner, a getaway to one of these romantic hotels is sure to deliver. Sleeping...
For her first international trip since 2020, Indagare’s Madeline Case traveled to Italy, one of her longtime favorite destinations. During her two weeks experiencing la dolce vita, she ventured from the shores of Lake Como to the coast of Tuscany,...
A trip here can easily be combined with these amazing destinations and more. Contact our team to craft the perfect itinerary.
Firenze, famously dubbed the “city of stone” by writer Mary McCarthy, regards itself as a living museum. And considering that it has counted among its residents the likes of Michelangelo, Raphael, Dante, Donatello, Brunelleschi and the entire Medici clan, it...
The small town of Forte dei Marmi is uniquely positioned between the dramatic mountain range of the Apuan Alps, dazzling with white marble caps that give the illusion of snow, and the glistening Tyrrhenian Sea. Prosperous from maritime trade, wealthy...
Rome is a place where ancient history and contemporary life breezily coexist, where you can sip cocktails at a trendy bar while gazing upon a temple colonnade from the year 145 (that would be at Salotto 42, on Piazza della...
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