When we are asked by potential first time visitors to Italy for suggestions and our idea of the perfect itinerary, it always comes down to "how long a trip are you able to plan"? along with any special interests that the clients may have. It's a terrible verdict on the American workplace that vacation time is so limited, and so sometimes we have just a week to work with. That means some hard decisions to narrow down a trip to just 2 or maybe 3 destinations at a push. Tuscany is nearly always on the brink of making it in, but then has to be cut as the 3 major cities of Venice, Florence and Rome tend to win out. It's a captivating region known for its timeless beauty, Renaissance art, rolling vineyards, and historic cities.
Here's the thing.
Stretch to 10 days and we are always going to urge you to experience Tuscany and for a minimum of 3 nights, hopefully considerably longer. Here you can relax, take time out from cramming city tours in, and breath in the absolute true sense and flavor of the country. For our own 3-week team trip we included 5 nights in the area and did not regret that for one second.
Here's our Top 5 from Tuscany.
Top 5 - Tuscany, Italy
1. Rosewood Castiglion del Bosco (above and 2 photos below)
Rosewood Castiglion del Bosco is a luxurious Tuscan retreat set in a restored 800-year-old estate, offering a harmonious blend of natural beauty, exquisite accommodations, and world-class amenities. We spent a half day here courtesy of our sales contact and the property blew us away. The calm, quiet location, the suite to multi-bedroom villa options, the food, the wine (produced in their own winery which can be toured), and simply the feel of this place which was once a hilltop village, all added up to a remarkable property.
2. Montepulciano (above and below)
Montepulciano is a charming hilltop town renowned for its exquisite beauty and rich history. Its ancient origins date back to the Etruscans and Romans, and the town's well-preserved medieval and Renaissance architecture captivated us. It's also famous for its exceptional wine, particularly Vino Nobile, a robust red wine produced in the surrounding vineyards. The town's streets are lined with picturesque squares, elegant churches, and historic buildings. Visitors can enjoy breathtaking views of the rolling Tuscan countryside from its elevated location. There are also wine tastings and cellar visits underneath the actual streets in seriously beautiful caves.
3. Pienza (above and below)
Only 20 minutes west of Montepulciano is Pienza. It's also renowned for its well-preserved Renaissance architecture, including the beautiful Piazza Pio II, flanked by the impressive cathedral and Palazzo Piccolomini. The town is also celebrated for its delicious pecorino cheese (above), produced locally. Nestled in the picturesque Val d'Orcia, Pienza offers stunning views of rolling hills and vineyards, making it a UNESCO World Heritage site and a must-visit destination for travelers seeking a taste of Italy's rich history and culture.
4. Truffle Hunting (above and below)
Hyperbole alert!!! This was the most enjoyable tour I have ever had when traveling. Yes, I'm a foodie and love a good stroll, but trust me, if you're even just mildly interested in the source of some of your food, let alone one of the most expensive food commodities going, the white truffle, then this is for you. Lili and Spagna, our 2 dogs were energetic supremos of truffle hunting, raking in 12 in total in our 90 minutes in the forest. They are trained expertly over many years.
And then you get to eat them! The truffles, not the dogs.
5. The Countryside (above and below)
It is dreamy.
When they say the rolling hills of Tuscany, they mean it.
Views, views and more views.
Olive oil and wine producers everywhere.
Smiles on your faces.
If you're ready to go on your own getaway, let us know and we'd be happy to plan an unforgettable trip. Click the button below to get started.
I love travel and I love travel planning just as much and I am proud to have built a team as passionate about exploring the world as myself. It took me a very long time to align my career with my undeniable passion for exploring, but now I and the team are here for you. Your personal travel tailors - award reservation and luxury custom itinerary experts. We provide a bespoke service, imagining and creating itineraries for independent minded families and groups.