6 exceptional spots for an authentic Tuscan holiday

We’ll start with the essentials. What’s your favorite gelato flavor? Classic cream? Salted caramel? Timeless pistachio? We’re asking for good reason—just nearby is a gelateria that Italian rankings have crowned for years. Your hosts also know all the best local bites, not just the sweet ones. In autumn, they’ll whisper secrets about where to find local truffles. We literally salivated, so here’s the address: the Arno river valley, between Florence, Arezzo and Siena. This is the quieter, more laid-back side of Tuscany, where you can uncork wine, take a dip in the pool, and lose track of the days. A six-person house nestled among vineyards and olive groves. Included: peace and quiet, and—of course—Italy’s best gelato.

You won’t find a more cinematic scene on Slowhop. Rolling fields, cypresses tracing winding roads, a stone borgo perched on a hill, olive groves and vineyards. Everything fits together like truffle and pasta. A private apartment scented with cypress and summer calm. There’s a pool, wine is never out of reach, and cycling routes start right outside your door—they’ll test even seasoned riders. It’s just a stone’s throw from the Ligurian Sea. Bonus: a host who knows exactly where the locals dine and which river they head to when the cicadas fall silent in the heat.

Ever feel like dropping everything and heading to the Bieszczady mountains in Poland? Lenka and her family almost did just that. They left their Prague life behind and chose the surroundings of Chianni in Tuscany instead. Now you can join this Czech family’s adventure and experience what it’s like to escape for a day or two. And since adventures are better together, there are two houses on site—one sleeps six, the other nine. The hosts know all the best spots and will guide you on where to start exploring.

This is for those who’d rather savor authentic Italian countryside life than opt for a hotel package. Picture rolling up your sleeves, flour on your hands, a tomato smudge on your chin, homemade tiramisu, and sunsets over Tuscan hills. For larger groups, rent the entire house; smaller parties can choose from the apartments—all nestled in an olive grove. They press liquid gold here, so you can dip, drizzle, and savor every drop. In autumn, slip on wellies and help with the harvest. Located between Pisa and Florence, with views over the Padule di Fucecchio valley. What was once a ruin of bare walls and a roof now features a pool with a view and plenty of space to lounge or get busy. Cooking classes, wine tastings, yoga sessions, even intimate weddings—they handle it all.

You know that feeling when you open a window and can’t help but let out an awestruck sigh? That’s what happens here—every single day. On one side, Lake Trasimeno shimmers in the sunlight; on the other, vineyards, cypresses, and picture-perfect Tuscan villages. No crowds, just peaceful privacy, good wine at the twist of a corkscrew, and a view you’ll remember more easily than your PIN. Expect home-style lunches like Nonna’s and lazy afternoons in the garden.