Live as deeply, as slowly, as quietly, or as vibrantly as you like.

A summer’s day:

In mid-summer, the sun is known to rise before 6 a.m., and if you’re a morning person, so will you. If the day is meant to be hot, it’s in these early hours that you’ll want to start a rustic, countryside walk, or a bike ride from Castiglione d’Orcia along the gently sloping road to Pienza. You’ll hear crowing and morning birdsong, and in the village, you’ll eventually hear the sound of espresso cups on saucers. On market day, you will find wonky-shaped yellow and red peppers, bright red tomatoes of all varieties, crisp local lettuces, and eggs from the land just below the ancient walls. Indulge in a freshly baked cornetto and make your way to the Abbazia di Sant’Antimo just before 10 a.m., so that you can have the abbey nearly to yourself and a moment with the lavender blowing in the breeze. A former Benedictine monastery, the mysticism that surrounds this Romanesque abbey will set the pace for the day.

Summer afternoons are ripe for shady activities. Take refuge from the hot sun inside Casa D’Orcia and delight in a big, fresh summer salad, or head over to Pienza for lunch under the canopy at the Townhouse Caffe. Here is where you can sample cuisine that is different from the ‘typical Tuscan’ menu: chianina tartare, the best burger in all the land, and a smashing burrata await. Enjoy a Rosso di Montalcino from Sesti. Maybe enjoy two. After lunch, stroll around Pienza, one of the most photogenic villages in all of Italy. Here you will find all kinds of shops, gourmet stores, and tasty gelato.

In the late evening, head over to Podere Il Casale, a working farm and restaurant in Pienza with some of the most magnificent views in all the land. Visit the baby goats, take a tour of the vegetable garden, participate in a cooking class, or simply take a seat at a panoramic table and watch the summer light change over the vista. The restaurant is known for its upscale simplicity. All of the produce comes directly from the enormous ‘orta’ found just below your table. Don’t miss the setting sun over the hills—this is one of the most extraordinary vantage points in all of Tuscany.

An autumn day:

Early morning is ideal for a truffle hunt. In the nearby town of San Giovanni D’Asso, the white truffle of Crete Senese is a rare but possible find. If accompanied by a fantastic guide and truffle-hunting dog, you may find yourself with a pungent addition to your pasta just in time for lunch.

In the afternoon, nestle into a table on Osteria La Porta’s terrace overlooking the cypress-dotted landscape between Monticchiello and Pienza. Creative pastas and a Bistecca Fiorentina will hit the spot, accompanied by a Vino Nobile. Dine slowly and savor the changing light over the fields.

After lunch, take a stroll around Bagno Vignoni, just eight minutes from Castiglione d’Orcia. Completely unique with its centered hot springs in the renaissance-era stone square, the village is well-liked by locals and extremely photogenic. The Via Francigena, the ancient travel route from England to Rome, is just a few minutes away, and you may find trekkers taking a pause around the piazza.

Have dinner at home at Casa d’Orcia, and afterward, grab a sweater and take a stroll in the village or up to Rocca d’Orcia. The cooler evening temperatures make the uphill climb that much easier!

A winter’s day:

Winter in the Val D’Orcia is both sunny and cozy, and you will find the roads less trafficked and the restaurants inhabited by more locals. The holiday season is a vibrant time of year, especially on weekends, when families drive from nearby cities to pass a lovely weekend in the countryside. Ancient villages such as San Quirico, Montalcino, Montepulciano, and Pienza will be lively and colorful, with everyone out shopping and filling their bags with food and wine for a winter feast.

In the afternoon, indulge in a little time at the thermal springs, which stay warm all year round. Saturnia, about an hour drive from the village, is famous for its hot springs. In winter, you will have the pools to yourself and will leave feeling completely rejuvenated. This sort of water therapy has been utilized since the 11th century and is still called upon for healing aches and pains.

If you decide to go out for dinner, the interior rooms of Ristorante Fonte Alla Vena in San Quirico d’Orcia will feel like the perfect spot for a winter’s evening. Here you will find all of the local classics such as pici all’aglione (handmade pici pasta with a special type of large garlic), peposo di vitello (a divine stewed veal made with red wine and peppercorn), and classic vegetables cooked to simple perfection, as well as a few unique dishes such as beef tartare with black truffle and parmigiano.

A spring day:

The temperature is perfect for a long cycle; how about the San Quirico to Pienza loop. This 39 mile loop is suitable for all levels. One of the highlights is the panoramic road with its painterly landscapes; known as one of the most beautiful roads in the region, it does not get more magnificent than this. The softly rolling hills, cypress trees, distant farmhouses, and completely open terrain will provide a peaceful balance to your long ride.

In the afternoon, walk or drive down from Castiglione d’Orcia to La Nascosta, a family-run winery literally ‘hidden’ below the village. Both the property and the wine are exceptional. The land here benefits from the extinct Monte Amiata Vulcan and the River Orcia, creating the perfect mixture of soils: stones and clay from the volcano, sediments of marine origin from the river. On the property, guests are welcome to take a tour and relax for a tasting of their exquisite Sauvignon blanc, Chardonnay, Sangiovese, and other vines. La Nascosta is proof that the Val D’Orcia can be home to incredible white wines, and to miss them, as well as the wonderful family who runs the property, would be a great shame!

A spring evening in and around Castiglione d’Orcia is a painter or photographer’s delight. Set up an easel or ask a friend to be your chauffeur as you photograph the greenest hills you’ve ever seen. Watch the tall grasses blow in the wind on your way to dinner at Il Leccio, where you will sit outside in the piazza, surrounded by locals who have been frequenting the trattoria for decades. The clock tower strikes, dinner is served, and someone has to finish that bottle of wine.