When a friend invites you to stay in a 16th-century palace in Siena, there’s really only one response. We started our week in Tuscany at the Grand Hotel Continental, a former aristocratic residence that has been elegantly transformed into a luxury hotel. Located just steps from Piazza del Campo, Siena’s beating heart, the hotel is a gateway into the city’s rich history. Unlike Florence, Siena offers a more tranquil experience—fewer crowds, quieter streets, and an intimate connection to its medieval and Renaissance roots. Staying at the Grand Hotel Continental, with its frescoed ceilings and historic architecture, only deepened our sense of connection to the town’s past.

While in Siena, we decided to focus on exploring the city’s lesser-known attractions. The Old City Ramparts, which encircle much of Siena, provided a perfect opportunity for a quiet stroll with panoramic views of both the city and the surrounding Tuscan hills. Walking along these ancient walls, it’s easy to get lost in the history, with each corner offering a new perspective on the city below. We also spent a peaceful afternoon at the Orto de’ Pecci, a medieval garden just a short walk from the city centre. The garden offers a peaceful respite from the bustle of Siena’s streets, with views of the city skyline framed by lush greenery.

For an authentic dining experience, we headed to Enoteca di Terzi, a small wine bar and restaurant tucked away in a side street near the Piazza del Campo. Here, the focus is on local, seasonal ingredients, with dishes like wild boar pappardelle and Tuscan bean soups taking centre stage. The wine list is extensive, showcasing the best of Tuscany’s vineyards, and the staff’s deep knowledge of regional wines made for an informative and enjoyable evening. It’s a perfect example of Siena’s ability to offer a refined culinary experience without the need for grandiosity.

Siena also offers a surprising range of cultural experiences. One highlight was a visit to the Teatro dei Rinnovati, located inside the Palazzo Pubblico. This historic theatre, with its intimate setting, regularly hosts performances ranging from classical concerts to contemporary plays. It’s a side of Siena that many visitors miss, but for those looking to engage with the city’s cultural life, it’s well worth attending a performance. We also made time for the Basilica di San Clemente in Santa Maria dei Servi, a lesser-visited church that offers a serene atmosphere and some beautiful frescoes. From the steps of the church, the view over the Tuscan countryside is stunning—another reminder of the city’s deep connection to the land around it.

Leaving Siena, we made our way to the quiet town of Pienza, which is often overshadowed by its better-known neighbour, Montepulciano. But while Montepulciano draws more attention for its wine production, Pienza has a quieter appeal. The town was designed by Pope Pius II during the Renaissance as an ideal city, and it’s easy to see his vision in the layout of the central piazza and the harmonious architecture. Despite its historical significance, Pienza remains relatively peaceful, its streets lined with local shops selling pecorino cheese and olive oil. It’s a town where you can take your time, enjoying the slower pace of life and the sweeping views over the Val d’Orcia.

We stayed at the Albergo Le Terme, a comfortable hotel that sits right in the heart of the small village of Bagno Vignoni. The hotel is perfectly positioned for those who want to explore the area’s famous thermal springs. The springs, which have been used since pre-Roman times, sit in the middle of the village’s main square, creating an atmosphere that feels both ancient and alive. Soaking in the thermal waters at Albergo di Terme was a restorative experience, offering a perfect way to unwind after days of walking and exploring.

While in Bagno Vignoni, we dined at two standout restaurants. La Bottega di Cacio, located near the Albergo Le Terme, is a small, unpretentious place that specialises in local Tuscan flavours. We enjoyed a selection of meats, cheeses, and their famous pecorino fresco. The platters are generous, and the focus on local ingredients makes this a great stop for a light lunch or early dinner. The views from the restaurant, overlooking the surrounding Tuscan hills, only add to the experience. Another favourite was Osteria del Leone, which focuses on traditional Tuscan dishes. The menu features simple yet rich flavours, with dishes like wild boar and fresh pasta made in-house. The ambiance is rustic, and the staff are knowledgeable about both the food and the local wines. It’s the kind of place where you settle in for the evening, enjoying the slower pace of life that defines this part of Tuscany.

From Bagno Vignoni, we drove to the coastal town of Pietrasanta, located near the Ligurian Sea. While nearby Lucca and Forte dei Marmi tend to attract more attention, Pietrasanta quietly holds its own as a place for those in the know. The town is best known for its connection to marble, with sculptors from all over the world coming to work in the local workshops. The town itself has a relaxed, unpolished charm, with cobblestone streets leading to the central Piazza del Duomo. Despite its reputation as an artists’ haven, Pietrasanta doesn’t feel overly touristy; it’s a working town with a vibrant local community.

Our base in Pietrasanta was the Albergo Pietrasanta, a hotel housed in two restored palazzi just off the town’s main square. The hotel offers a comfortable, low-key stay, with rooms that are spacious and quiet. From here, it’s an easy walk to the beach or to one of the town’s many restaurants. One afternoon, we took a short drive to the nearby Felice Beach Club. While the Versilia beaches can get crowded in summer, Felice offers a more laid-back experience. You can rent a comfortable chair or lounge, enjoy the sun, and then head to their simple restaurant for freshly grilled fish. It’s an ideal spot for those who want to spend a relaxing day by the sea without the fuss of more commercial beach clubs.

In Pietrasanta, we also dined at La Dogana, a rustic restaurant located just outside of town. The menu focuses on seasonal, local ingredients, with dishes like slow-cooked beef and roasted vegetables that showcase the simplicity and richness of Tuscan cuisine. The setting, surrounded by hills, makes it a great spot for a long, leisurely meal. Another standout was Bistrot Bagno Primavera Versilia, a restaurant located closer to the beach. Known for its seafood, it’s the kind of place where you can enjoy fresh, grilled fish with a glass of local white wine, all while listening to the sound of the waves nearby.

Pietrasanta itself is also worth exploring on foot. The town has a laid-back atmosphere, and the local galleries and workshops are open to visitors, offering a chance to see marble sculptors at work. We spent a morning walking through the town, stopping at the weekly produce market, and then ventured up into the hills for a circular walk via Capezzano and Capriglia. The route takes about two hours and offers stunning views of both the Apuan Alps and the sea. For lunch, we stopped at the Circolo SOMS Capriglia, a small agriturismo where you can enjoy a simple, rustic set menu. It’s the kind of hidden gem that makes Tuscany such a rewarding place to explore.

This week off the beaten track in Tuscany was a reminder that some of the best experiences come in the quieter, lesser-known corners of the region. Whether relaxing in the thermal springs of Bagno Vignoni, wandering the streets of Pietrasanta, or dining in a tucked-away osteria in Siena, Tuscany’s quieter towns and villages offer a more authentic experience—one that’s rich in history, food, and the rhythms of daily life.