
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.
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Perfect forFamilies | Foodies | Romantics | Ultimate Indulgers
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When to goMarch-May | June-August | September-November
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Ideal length of stay1 Week
Designing Your Journey
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.
1 Week: Essential Tuscany
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.
Days 1-2: The Tuscan Spirit
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.
Day 3: Special Experiences
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.
Day 4-5: Day Trips
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.
Where To Stay
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.
- The Borgo. Courtesy Rosewood Castiglion del BoscoRead More
Rosewood Castiglion Del Bosco
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...
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Il Borgo (at Castello Banfi)
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.
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Belmond Castello di Casole
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...
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Borgo Santo Pietro
This painstakingly restored Borgo near Siena has upped the luxury ante for the area.
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Monteverdi
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.