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Where to Stay in Tuscany

Choosing the right base in Tuscany sets the tone for your entire trip.
Whether you picture yourself among the vineyards of Chianti, in a hillside villa near Cortona, or in the elegant countryside around Lucca, each area offers its own rhythm and beauty.

With over twenty years of first-hand experience inspecting villas, apartments, and boutique hotels, I help travelers find the perfect match — from intimate escapes to multigenerational family gatherings.

Explore insider tips on the best areas to stay, what makes each unique, and how to plan your ideal villa holiday in Italy.

➡️ Read the full guide: Where to Stay in Tuscany

Planning your first trip to Italy? Ensuring seamless connectivity is essential for navigating the beautiful streets, staying in touch with loved ones, and sharing your experiences. One of the most cost-effective ways to achieve this is by obtaining a local SIM card. Here's everything you need to know.

Discover the best things to do in Cortona, Tuscany — from iconic sights made famous by Under the Tuscan Sun to local hidden gems, scenic day trips, and unforgettable food and wine experiences. This guide also features a rare find: a 7-bedroom luxury villa with a private pool, located inside Cortona’s historic town walls. Ideal for family holidays or group escapes, it’s the perfect way to live like a local in one of Tuscany’s most charming hill towns.

So You Want to Stay in Tuscany?
Tuscany is full of dreamy landscapes, historic towns, and unforgettable food and wine—but choosing the right area to stay in can make all the difference. From the central convenience of Chianti, to the cinematic hills of the Val d’Orcia the coastal charm of Lucca, and the elegance of Cortona—here’s how to choose the best base for your Tuscan adventure.