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I like to choose an Italian region for its own rhythm, then give it enough time. Rome rewards long walks between ancient landmarks and neighborhood tables; Florence and Tuscany pair Renaissance art with vineyards and hill towns. In the Dolomites, the mountains and the season set the pace, while Sardinia calls for coastal drives, clear-water coves, and time in its villages.

My favorite approach is to leave breathing room between the famous sights. Choose a city trip, a Tuscan or Sardinian road journey, or an alpine adventure from this collection, then let the smaller moments become part of the trip.

Pienza is a charming small town in the heart of Tuscany. Known for its stunning Renaissance architecture, Pienza was named a UNESCO World Heritage Site in 1996. The town was originally known as Corsignano until it was transformed by Pope Pius II in the 15th century into a model Renaissance town.

Pienza's most notable landmark is the Piazza Pio II, which is surrounded by impressive Renaissance buildings, including the Palazzo Piccolomini, the Duomo di Pienza, and the Palazzo Borgia. The town is also famous for its Pecorino cheese, which is produced using traditional methods in the surrounding countryside. You can enjoy a cheese tasting and learn about the cheese-making process at one of the many cheese shops and dairy farms in the area.

Overall, Pienza is a picturesque town with a rich history and cultural heritage that is worth exploring.

Official website

Pienza

Colorful fishing villages, coastal trails, sea views, and leisurely Ligurian meals.

Cinque Terre Escape

Alpine hikes, mountain lakes, winding roads, and quieter corners of northern Italy.

Dolomites Adventure

Dramatic peaks, turquoise lakes, alpine villages, and the Dolomites' defining views.

Dolomites Highlights

Renaissance masterpieces, grand churches, artisan streets, and long Tuscan lunches.

Florence Escape

Neighborhood wandering, remarkable art, Roman food, and time beyond the headline sights.

Roman Holiday

Ancient icons, grand piazzas, Vatican treasures, and the lively streets of central Rome.

Rome Escape

Wild coves, coastal drives, ancient villages, and the rugged heart of Sardinia.

Sardinian Adventure

Val Gardena slopes, with Cortina extensions for confident skiers new to the Dolomites.

Ski the Dolomites

Renaissance cities, vineyards, and hill towns, with colorful coastal extensions.

Tuscan Adventure

Nestled in the heart of Tuscany, this town is a haven for wine lovers. Wander the Renaissance streets, taste the renowned Vino Nobile, and enjoy the sweeping views of the Tuscan hills.

Montepulciano

Walk within the historic center and use a car for countryside properties, hill towns and the wider Tuscan route. Mainline or regional rail reaches some towns but does not serve every hotel or village. Park outside restricted centers and check the exact property’s access instructions.


Castello di Reschio is a castle hotel on a private Umbrian estate close to the Tuscan border. A thousand-year-old fortified building forms the hotel’s center, surrounded by restored farmhouses and an extensive rural landscape.

The rooms combine historic spaces with carefully considered contemporary design and individual furnishings. A pool in private gardens, several dining and drinking spaces, and a bathhouse in former cellars give guests reasons to spend substantial time at the property. Estate villas are a different accommodation product from the castle’s hotel rooms.

This is a destination stay for travelers who value design, space and a slower pace. Reserve the exact room through the hotel’s official site and confirm dining, bathhouse treatments and activities separately. Its secluded setting requires transport planning; do not treat it as a town hotel or assume every estate experience is included in the room rate.

Castello di Reschio

Cretaiole is a family-run farmhouse stay near Pienza, set on a Val d’Orcia hilltop with wide countryside views. The property is set on a hilltop with panoramic views of the surrounding countryside, including rolling hills, vineyards, and olive groves.

The accommodations at Cretaiole consist of a series of comfortable apartments and independent houses, each with its own unique character and charm. The apartments range in size from cozy one-bedroom units to spacious three-bedroom homes, and all are decorated in a rustic Tuscan style with stone walls, wood-beamed ceilings, and traditional furnishings.

Guests at Cretaiole can enjoy a range of activities, including swimming in the outdoor pool, playing tennis on the on-site court, and exploring the beautiful surrounding countryside on foot or by bike. The property also offers cooking classes and wine tastings, giving visitors a chance to experience the best of Tuscan cuisine and wine culture.

Overall, Cretaiole is a wonderful choice if you are seeking a peaceful and authentic Tuscan experience with comfortable accommodations, breathtaking views, and plenty of activities to keep everyone entertained.

Cretaiole

La Bandita Townhouse is a luxury boutique hotel located in the heart of Pienza, a small Renaissance town in the Tuscan countryside. The hotel features spacious and elegant rooms, each individually decorated with a mix of vintage and contemporary furnishings, original artwork, and luxurious bedding.

The hotel's public spaces include a cozy lounge with a fireplace, a library with a curated collection of books and magazines, and a sun-drenched terrace with panoramic views of the town and surrounding hills. You can enjoy a complimentary breakfast each morning featuring locally-sourced ingredients, and there is also an on-site bar serving a variety of cocktails and wines.

La Bandita Townhouse offers a prime location for exploring the charming town of Pienza and the surrounding area, with its rolling hills, vineyards, and medieval hilltop towns.

The hotel also offers a range of experiences, including cooking classes, wine tastings, and guided tours of the region's cultural and natural attractions.

La Bandita Townhouse

Le Ragnaie is a charming agriturismo located in the heart of Tuscany. This family-run farm offers a peaceful and authentic Tuscan experience, surrounded by the breathtaking scenery of rolling hills, olive groves, and vineyards. The farmhouse has been beautifully restored, retaining its original character and features, while providing modern comforts and amenities.

The accommodations at Le Ragnaie are spacious and comfortable, with a rustic charm and elegant simplicity. Each room is individually decorated, featuring traditional Tuscan elements such as exposed stone walls, wooden beams, and antique furnishings. You can choose between rooms, suites, and apartments, all with stunning views of the countryside.

Le Ragnaie is also a working farm, producing its own wine and olive oil, which guests can sample and purchase during their stay. The farm also offers cooking classes, wine tastings, and guided tours of the vineyards and olive groves. You can relax by the pool, explore the nearby medieval villages, or take a scenic drive through the picturesque countryside.

Whether you're looking for a romantic getaway, a family vacation, or a relaxing escape, Le Ragnaie offers a truly authentic Tuscan experience, filled with warmth, hospitality, and natural beauty.

Le Ragnaie

Terre di Nano is an agriturismo located in the Tuscan countryside near Monticchiello. Surrounded by olive groves and vineyards, the property offers panoramic views of the rolling hills of Val d'Orcia. The rooms and apartments are decorated in a rustic Tuscan style and feature wooden beams, terracotta floors, and antique furniture. Some units also have a private terrace or balcony.

You can enjoy a buffet breakfast made with local ingredients, as well as a variety of homemade products such as bread, jams, and cakes. The property also produces its own wine and olive oil. Other amenities include an outdoor pool, a garden, and a sun terrace.

Terre di Nano is an excellent choice for those looking for a peaceful and authentic Tuscan experience.

Terre di Nano

Villa di Piazzano is a historic villa located in the Tuscan countryside, just outside of the city of Cortona. The villa dates back to the 1460s and has been restored to offer modern amenities while maintaining its original features, such as frescoed ceilings, antique furnishings, and a centuries-old park.

The rooms at Villa di Piazzano are elegantly furnished and offer views of the surrounding hills or the garden. They feature modern amenities while also retaining their traditional charm with antique furnishings and original artwork.

The villa also offers a range of facilities, including an outdoor swimming pool, a garden, and a restaurant serving traditional Tuscan cuisine made with locally sourced ingredients.

You can also participate in cooking classes, wine tastings, and guided tours of the surrounding area.

Pienza

Explore Italy itineraries

Curated stays in Montepulciano

Villa di Piazzano

Castello di Reschio

Le Ragnaie

La Bandita Townhouse

Cretaiole

Terre di Nano