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Tuscany was love at first sight on our first Italian road trip, charming us with its timeless beauty. Losing yourself in the rolling hills, indulging in the rich flavors of Tuscan cuisine, exploring the treasures of Florence, or immersing yourself in the idyllic countryside dotted with ancient castles — Tuscany awakens your senses and leaves you longing for more.

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.

Pienza

A mini-trip to explore this tiny Italian gem, hopping between picturesque villages.

Cinque Terre Escape

Escape to one of the cultural capitals of the world for its museums and architecture.

Florence Escape

Explore the bustling Florence, Cinque Terre, and Tuscan countryside.

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

Even though Castello di Reschio is technically located outside of Tuscany, this luxury estate is a destination itself. The estate spans over 2,700 acres of rolling hills, olive groves, and vineyards. The property features a 10th-century castle that has been beautifully restored and converted into a stunning boutique hotel. Each of the rooms and suites at Castello di Reschio is elegantly decorated with antique furnishings, fine linens, and artwork. The estate also has several private villas available for rent, each with its own private pool and breathtaking views of the surrounding countryside.

You can enjoy a range of activities during your stay, including horseback riding, cycling, tennis, and hiking. The estate also has its own winery with wine tastings and tours of the vineyards. The restaurant at Castello di Reschio serves delicious Italian cuisine made with locally sourced ingredients, and there is also a bar where you can enjoy cocktails and aperitifs.

Overall, Castello di Reschio is the perfect destination for those looking to experience the beauty and charm of the rolling hills of Italy in a luxurious and serene setting.

Castello di Reschio

Stay on a family-run farmhouse located in the heart of Tuscany's Val d'Orcia region, just outside the small town of Pienza. 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 Tuscany itineraries

Curated stays in Montepulciano

Villa di Piazzano

Castello di Reschio

Le Ragnaie

La Bandita Townhouse

Cretaiole

Terre Di Nano