Siena Escape: 2-days journey from Rome on a historic Italian train

Travel from Rome to Siena for a curated taste of Tuscan life including history, wine, and timeless beauty, all without the hassle.

Day 1: Journey to Siena aboard a Historic Italian Train

Your experience begins the moment you step onto a legendary historic train of the Italian State Railways in Rome. As the vintage carriages roll through the Tuscan countryside, you’ll be immersed in the timeless charm of Italy’s golden age of rail travel. Upon arrival in Siena, enjoy a private transfer to the historic city center, where you’ll have some free time to grab lunch and take in the atmosphere. After lunch, meet your expert local guide for an immersive walking tour through the heart of Siena. Highlights include the magnificent Cathedral, the frescoed Piccolomini Library, Palazzo delle Papesse, and the breathtaking panoramic terrace overlooking the city’s terracotta rooftops and surrounding hills.

Visit a traditional enoteca and savor local products

Following your cultural exploration, enjoy a guided visit to a traditional enoteca in the city center. Here, you’ll indulge in a tasting session featuring carefully selected local wines and authentic Tuscan products—a perfect moment to unwind and savor the region’s rich culinary heritage. This experience not only delights the palate but also deepens your connection with the land and its traditions. After the tasting, your private driver will transfer you to your hotel for check-in and a relaxing overnight stay in Siena.

Day 2: Slow Morning & Return to Rome

After a restful night in your handpicked hotel, wake up to a delicious breakfast and enjoy a leisurely morning to explore Siena at your own pace. Whether you want to sip espresso in a quiet piazza or take one last photo of the iconic Torre del Mangia, the time is yours to enjoy. When ready, your private driver will escort you back from the hotel to the train station for your return journey to Rome, enriched by the essence of Tuscany.

Alternative experiences available

Once arrived in Siena from Rome, you can choose to enrich your journey with one of three itineraries:

• Siena Divina – Easy: offers a half-day guided tour of Siena, covering the Cathedral, Piccolomini Library, Palazzo delle Papesse, and the panoramic terrace, followed by a tasting at a local enoteca. Overnight stay is included, or the experience can be booked as a land-only option without accommodation, with transfers to and from the station by public bus.
• The Flavors & Sights of San Gimignano: includes a scenic drive to this medieval gem, a winery visit with tasting and lunch, a guided tour of the town, and a stop for award-winning gelato before returning for the overnight stay.
• Chianti Charm: Monteriggioni & Radda: features guided visits to both villages, a winery tour with tasting and lunch, plus free time to explore at your own pace.

Even these last two options are also available as land-only options without accommodation.

To book, request assistance, or obtain more information, please contact [email protected].