Itinerary Details
1 Arrive Perugia, Italy
Perugia is a city of layers, where Etruscan walls, medieval streets and Renaissance palaces converge in a vibrant blend of history and culture. Beneath its surface, ancient passageways whisper stories of popes and power, while above, lively piazzas and sweeping views reveal the soul of Umbria.
Meals:
2 Perugia – Where Past And Present Converge
A place so poetic it’s mentioned in The Divine Comedy, Perugia is a historic city in Umbria’s center, known for its travertine marble, Etruscan arches and medieval walls. Despite its ancient architecture, it remains a lively student hub with a full calendar of music, wine and food festivals. Admire the Gothic grandeur of Palazzo dei Priori and the Cathedral of San Lorenzo, symbols of Perugia’s medieval power and artistic legacy. Wander quiet alleys and scenic overlooks, where Etruscan roots and Renaissance beauty blend with the city’s youthful energy.
Meals:
3 Assisi – Hallowed GroundUncover centuries of history and culture in the sacred city of Assisi as you explore the Gothic masterpiece and revered pilgrimage site, the Basilica of San Francesco. Navigate Assisi’s winding streets, passing churches, majestic palaces and charming squares.
Meals:
4 Cortona – Into The Tuscan CountrysideSouthern Tuscany is beloved for its soft light and undulating landscapes, home to vineyards and olive groves that produce some of Italy’s most mouthwatering flavors. Begin your Tuscan adventure in the picturesque hilltop town of Cortona, where a guided tour introduces cobblestone streets lined with artisan shops and inviting cafés.
Meals:
5 Pienza And Montepulciano – Classic Enclaves Of The Val D’orciaVisit two quintessential Tuscan towns in the Val d’Orcia, a UNESCO World Heritage Site known for its striking landscapes and cultural legacy. Begin in Pienza, home to a Renaissance town center reimagined by Pope Pius II in the 15th century. Continue into the countryside for a tour and lunch at a local farm. Conclude in Montepulciano, where Renaissance palazzi and churches crown the hilltop, and enjoy an exclusive tasting of Vino Nobile di Montepulciano at an organic wines estate.
Meals:
6 Val D’orcia – Brunello Wine Tasting And Bagno VignoniDiscover the serene beauty of the Val d’Orcia, a UNESCO World Heritage Site of rolling hills, vineyards and timeless villages. Visit a renowned Brunello di Montalcino winery for a tour and tasting, followed by a light lunch in the countryside. Pause at the atmospheric Abbey of Sant’Antimo, then stroll through the thermal village of Bagno Vignoni, where quiet charm and history meet.
Meals:
7 Siena – Medieval MajestyStep into Siena, where medieval splendor and civic pride fill every winding street. Explore the Gothic Duomo and the richly adorned Piccolomini Library, then walk through Piazza del Campo, home to the legendary Palio horse race. Discover the city’s vibrant contrade traditions and admire the frescoes and architecture of the Palazzo Pubblico — timeless symbols of Siena’s cultural heart.
Meals:
8 Depart Southern TuscanyMeals:
