BY: ARTFUL HOTELS
Tuscany’s beauty lies in its variety. One moment you’re walking through a Renaissance piazza, the next you’re driving past fields of sunflowers and cypress-lined roads that seem to stretch forever.
In this guide, we cover the places worth your time, including four countryside hotels handpicked by Artful experts.
Spend a couple of days in Florence exploring its grand piazzas, frescoed chapels, and artisan shops. Cross the river into the Oltrarno for quieter streets and some of the city’s best trattorias, and don’t miss the Uffizi Gallery for a close-up look at Renaissance masterpieces.
Outside the city, Siena is a must with its fan-shaped piazza and striped Gothic cathedral. San Gimignano, with its medieval towers, is another Tuscan classic. In the Val d’Orcia, golden hills lead to postcard-perfect villages like Pienza, Montepulciano, and Montalcino. Bagno Vignoni is worth a stop to see its ancient thermal baths right in the middle of the square.
If you’re looking for smaller, quieter towns, Monticchiello is a lovely choice, with stone streets, flower-draped balconies, and far-reaching views over the Val d’Orcia. Certaldo also charms with its red-brick streets and literary history.
When you’re ready for the coast, the Maremma offers wide sandy beaches, pine forests, and laid-back seafood spots. For something more off the radar, hop over to Elba Island for turquoise coves and historic port towns.
Eating in Tuscany is all about seasonal ingredients and tradition. In Florence, start your morning with a cappuccino and stuffed brioche at a neighborhood café, like Caffè Gilli. For lunch, order a bowl of ribollita from Trattoria Marione, the hearty bread and vegetable soup that’s been a staple for centuries. And for dinner, you have to get a Bistecca alla Fiorentina from Trattoria Sostanza.
In Siena, try pici pasta with cacio e pepe or wild boar ragù, paired with a glass of Chianti Classico from the surrounding vineyards. The hill towns of the Val d’Orcia are the place to sample pecorino cheese, Pienza is especially known for it, often served with honey or truffle shavings. On the coast, cacciucco is the must-try dish, a rich fisherman’s stew with plenty of garlic and a little heat.
Set between Montepulciano and Pienza, Lupaia feels like a Tuscan daydream made real. The farmhouse rooms are layered with stone walls, hand-painted tiles, and weathered beams, while gardens spill into panoramic views of the Val d’Orcia. Meals are served family-style from the open kitchen, often with produce from the property’s own garden. Evenings end with wine on the terrace as the hills fade into dusk.
On the Umbrian-Tuscan border, Reschio is a thousand-year-old estate transformed into a sprawling retreat of stone farmhouses, olive groves, and rolling meadows. Interiors by Count Benedikt Bolza blend centuries-old architecture with custom furniture and contemporary art. The estate includes a castle hotel, riding stables, and a wellness center tucked into the old wine cellars. It’s grand yet intimate, with every detail executed to perfection.
Overlooking the Tyrrhenian Sea on the Argentario coast, Il Pellicano has been an icon of Italian seaside glamour since the 1960s, once frequented by legendary photographer Slim Aarons. The interiors are breezy and refined, with terracotta floors, whitewashed walls, and rattan accents. Days are spent by the saltwater pool or swimming off the private jetty, while evenings bring Michelin-starred dining and unforgettable sunsets.
This 12th-century convent near Città della Pieve has been reimagined as a contemporary sanctuary. Original stonework and vaulted ceilings meet sleek modern furnishings, creating a space that feels both rooted and forward-looking. The walled garden, lavender paths, and serene courtyards make it a true escape.
Discover more Artful Tuscany hotels here.
