TUSCANY & UMBRIA Sacred Landscapes Journey

From the sacred forest of St. Francis to medieval pilgrimage trails to an ancient Etruscan and Roman sanctuary, join us as we step out of today’s frantic world and into landscapes shaped by centuries of reflection, ritual, and quiet discovery. Here, we walk in the footsteps — quite literally — of St. Francis himself, visit awe-inspiring churches, explore ancient sites filled with history, wonder, and meaning, and even witness the extraordinary beauty of the Tuscan countryside from above during a sunrise hot air balloon flight before exploring the medieval splendor of Siena.

This journey invites you to slow your pace, breathe a little deeper, and experience Italy through places that have drawn travelers, pilgrims, and seekers for thousands of years. Along the way, we gather around tables rooted in local tradition, walk gentle historic paths, and immerse ourselves in the timeless beauty of Tuscany and Umbria’s most evocative landscapes — from quiet hill towns and sacred woodland paths to Siena’s vibrant medieval streets and sweeping vineyard vistas.

Throughout the week, you’ll experience moments that reflect the deep cultural and spiritual traditions of this region — soaking in mineral-rich thermal waters long believed to restore body and spirit, enjoying a private visit inside a humble countryside church that has honored women and mothers for centuries, discovering the fascinating symbolism woven into medieval art and architecture, and standing within an extraordinary active archaeological sanctuary where recent discoveries are reshaping our understanding of ancient spiritual traditions.

In Assisi, you’ll stand before Giotto’s remarkable frescoes honoring the life of San Francesco, gaining a deeper understanding of the man and the legacy he left behind. In Città della Pieve, you’ll experience living traditions that have welcomed pilgrims for centuries, from sharing meals inspired by sacred culinary customs to walking ancient pilgrimage routes through the surrounding countryside. In Siena, you’ll encounter the grandeur of Renaissance life and witness the Tuscan landscape revealed from above during a sunrise hot air balloon flight.

Equally meaningful are the moments shared around the table, where farm-to-table meals, local wines, and traditional recipes reveal how food has served as both nourishment and spiritual anchor to the people of this land for generations.

The rhythm of this journey is intentionally unhurried, allowing each day to unfold with balance and ease. There will be time to pause in quiet chapels, linger over meals, and simply absorb the beauty of the landscape without feeling rushed from one place to the next.

Walks are thoughtfully paced and designed for observation and connection rather than strenuous challenge, but guests should be comfortable walking independently on uneven historic paths and countryside trails.

WHAT YOU’LL Experience

• Walk in the footsteps of St. Francis while exploring Assisi’s sacred basilica and spiritual landscapes
• Stroll through the peaceful Sacro Bosco di San Francesco and historic pilgrimage paths once traveled by seekers for centuries
• Experience a sunrise hot air balloon flight over Tuscany, witnessing the landscape from a breathtaking new perspective
• Explore the medieval treasures and vibrant cultural heritage of Siena
• Discover the charming hill town of Città della Pieve, long a refuge for pilgrims traveling from northern Europe to Rome
• Participate in a hands-on cooking experience exploring sacred foods, ancient dishes, and culinary traditions connected to Italy’s seasonal and cultural celebrations
• Walk in the footsteps of pilgrims traveling toward Rome along the ancient Via Romea, where the trail opens to sweeping panoramic views across the Val d’Orcia
• Visit a countryside church deeply connected to local traditions honoring women and mothers, followed by a community-prepared countryside meal
• Enjoy farm-to-table dining experiences showcasing regional wines and seasonal Umbrian and Tuscan cuisine
• Experience a private visit inside a remarkable active archaeological excavation revealing an Etruscan and Roman sanctuary
• Soak in mineral-rich thermal waters at Fonteverde Spa, where Medici nobility once sought restoration, overlooking the Tuscan countryside
• Discover the symbolism and storytelling woven into medieval sacred art and architecture
• Enjoy unhurried time to wander historic hill towns, quiet chapels, artisan shops, and scenic piazzas

TRIP ITINERARY

Day 1, Sunday, November 1: Arrival in Assisi: Entering the Sacred Landscape

• Highlights: Welcome and trip introduction
• Dinner

Upon arrival in Italy, our private drivers will greet you and transport you through the rolling countryside of Umbria to Assisi, one of Italy’s most spiritually significant and beautifully preserved medieval hill towns. Rising gently above the valley below, Assisi has welcomed pilgrims, travelers, and seekers for centuries, offering a sense of peace that is felt almost immediately upon arrival.

After settling into your boutique hotel in the historic center, you’ll take part in a relaxed orientation walk through the town’s winding stone streets. As you explore quiet piazzas, artisan shops, and centuries-old architecture, you’ll begin to absorb the timeless atmosphere that defines Assisi and sets the tone for the week ahead.

This evening, we’ll gather for a welcoming dinner featuring seasonal Umbrian specialties and regional wines. Over dinner, you’ll get to know your fellow travelers on this shared journey of discovery and connection. As the day comes to a close, you’ll settle into the peaceful rhythm of Assisi, marking the beginning of your Sacred Landscapes experience.

Day 2, Monday, November 2: Assisi: Walking in the Footsteps of Saint Francis

• Highlights: Basilica di Assisi, ring walk Assisi
• Breakfast, lunch, dinner

This morning you’ll begin your exploration of Assisi with a guided visit to the Basilica of Saint Francis, one of the most revered pilgrimage sites in Italy. Inside this extraordinary complex, you’ll stand before Giotto’s masterful frescoes depicting the life of Saint Francis, gaining a deeper understanding of the man, his radical simplicity, and the spiritual legacy he left behind. Through art and architecture, the story of Francis unfolds in vivid color and remarkable detail, offering insight into the profound cultural and religious influence of this small Umbrian town.

Midday, we’ll gather for a relaxed lunch featuring seasonal Umbrian cuisine, offering time to enjoy regional flavors while sharing impressions of the morning’s experience.

The afternoon is intentionally unhurried, allowing you time to explore Assisi independently. You may choose to visit additional chapels and churches, wander through artisan shops, sit in a quiet piazza with a journal, or simply absorb the peaceful rhythm of daily life in this remarkable town.

As evening falls, you’ll enjoy dinner together in Assisi, savoring regional specialties while reflecting on a day immersed in the spiritual and artistic traditions that have drawn travelers here for centuries.

Day 3, Tuesday, November 3: From Assisi to Perugia: Sacred Landscapes & Living Traditions

• Highlights: Sacro Bosco di San Francesco, Perugia, arrival Città della Pieve
• Breakfast, lunch, light dinner

This morning we’ll bid farewell to Assisi and take our journey deeper into the Umbrian countryside with a visit to the Sacro Bosco di San Francesco, a protected woodland landscape closely connected to the spiritual legacy of Saint Francis. Following gentle walking paths through olive groves and peaceful forest trails, you’ll experience a setting that reflects Francis’ profound reverence for nature and offers a quiet moment of reflection.

Traveling onward, we’ll arrive in Perugia, the vibrant capital of Umbria. Here, you’ll have time to explore at your own pace. You may choose to visit the celebrated Galleria Nazionale dell’Umbria, browse artisan boutiques along Corso Vannucci, before we gather together for lunch at a welcoming trattoria.

In the afternoon, we’ll visiting the spectacular Abbazia di San Pietro, a Benedictine abbey that has served as a center of faith, scholarship, and artistic heritage for centuries, before continuing on to Città della Pieve, a charming hill town rich in artistic and cultural traditions that will serve as your home for the remainder of the journey. After settling into your boutique hotel, you’ll gather for a welcoming dinner featuring regional specialties.

Day 4, Wednesday, November 4: Sacred Traditions of Città della Pieve: Food, Faith, & Pilgrimage

• Highlights: Churches and pilgrims walking tour, cooking lesson, pilgrimage trail
• Breakfast, lunch, dinner

This morning we’re off to explore Città della Pieve, and to learn how it was shaped by centuries of pilgrimage. Located along historic routes connecting Rome with northern Europe, the town long served as a refuge for travelers journeying on foot. Its churches and religious institutions offered shelter, spiritual guidance, and renewal — traditions of hospitality that remain part of the town’s identity today.

Late morning, you’ll enjoy a hands-on cooking experience with local chef Cristian, preparing dishes connected to religious celebrations and seasonal Italian traditions. As you cook and share lunch together, you’ll discover how food has long served as both nourishment and ritual in Italian culture.

After time to relax or explore the town on your own, we’ll set out on foot along a section of the ancient Via Romea pilgrimage route, a historic trail that once guided travelers from Germany southward to Rome. Walking at a gentle pace through the countryside, you’ll experience the timeless tradition of pilgrimage and its connection to the landscape.

Your walk will lead to a small countryside church long associated with local women and mothers. Here, members of the community will welcome you with a simple grilled meal prepared over an open fire. Weather permitting, you’ll enjoy this meal picnic-style in the peaceful countryside before returning to town in the evening.

Day 5, Thursday, November 5: Siena: Tuscan Landscapes from Above and Medieval Beauty

• Highlights: Hot air balloon ride, excursion to Siena
• Breakfast, lunch, dinner

This morning is nothing less than extraordinary. Before dawn, we’ll depart Città della Pieve in the quiet stillness of early morning, setting out on what feels much like a pilgrimage of its own. As the landscape gradually awakens, we’ll travel toward the Tuscan countryside near Siena for a sunrise hot air balloon flight that offers a rare opportunity to witness the land from above.

As the sun rises over vineyards, olive groves, and rolling hills dressed in autumn colors, we’ll drift peacefully above the landscape, taking in breathtaking views that reveal Tuscany’s extraordinary beauty from a unique and contemplative perspective.

For guests who prefer to remain on the ground, a private driver will bring you directly to Siena, where you’ll enjoy a guided walking tour through the historic center, exploring medieval streets, the magnificent cathedral, and the iconic Piazza del Campo while learning about the city’s rich civic and religious history.

Later in the morning, both groups will meet in Siena where you’ll have free time to explore, browse artisan shops, or relax in one of the city’s charming cafés. You’ll then gather for an early lunch at a traditional trattoria, enjoying Tuscan specialties in a welcoming and convivial setting.

Returning to Città della Pieve in the afternoon, you’ll have time to relax or explore the town at your leisure. This evening, you’ll meet at a favorite local café for apericena, a relaxed Italian tradition combining aperitivo drinks with a generous assortment of regional dishes.

Day 6, Friday, November 6: San Casciano dei Bagni: Sacred Waters & Ancient Rituals

• Highlights: Excursion to San Casciano dei Bagni, archeological site, Fonteverde Spa
• Breakfast, lunch, dinner

This morning we’ll travel to the historic hill town of San Casciano dei Bagni, long known for its thermal waters. Here, you’ll enjoy a private visit inside an active archaeological excavation at the remarkable sanctuary of Bagno Grande, where recent discoveries of extraordinary Etruscan and Roman artifacts are reshaping our understanding of ancient spiritual traditions.

Following this extraordinary visit, we’ll enjoy a light lunch at our friend, Daniela’s, restaurant, before continuing to Fonteverde Spa, a renowned thermal spa overlooking the Tuscan countryside. Here, you’ll have time to soak in mineral-rich waters long believed to restore both body and spirit. This peaceful experience offers the perfect opportunity to relax and reflect on the week’s shared journey.

This evening, you’ll gather for a farewell dinner in Città della Pieve, celebrating the flavors, traditions, and friendships formed throughout the week, and an opportunity to reflect on our shared Sacred Landscapes experience.

Day 7, Saturday, November 7: Departure

Early morning departure for Rome Fiumicino Airport

4 STAR ACCOMMODATIONS

Asisium Boutique Hotel: Located in the heart of Assisi’s historic center, Asisium Boutique Hotel offers an elegant boutique stay within beautifully restored historic buildings that reflect the town’s medieval character. Blending modern comfort with timeless atmosphere, the hotel places guests steps from Assisi’s winding stone streets, sacred landmarks, and quiet piazzas, creating an immersive experience in one of Italy’s most spiritually significant hill towns.

Boutique Hotel Vannucci: Hotel Vannucci began as a retreat created by Vittoria Spinola, daughter of King Vittorio Emanuele II, who built elegant countryside villas in Città della Pieve in the late 1800s. One of the villas became Hotel Vannucci in 1903, and today the property maintains the charm and refinement of its origins, offering gracious guest rooms, marble bathrooms, and inviting gardens. Located just outside the medieval walls, the hotel provides a peaceful and refined stay within easy reach of Città della Pieve’s historic center.

INCLUSIONS

• 2 nights stay Assisi
• 4 nights stay Città della Pieve
• Group transportation by private transport service to/from Rome Fiumicino Airport on arrival and departure dates
• Private transport service to/from all towns and sites included in the itinerary, including, Perugia, Siena and San Casciano dei Bagni
• All breakfasts
• 6 dinners
• 3 lunches
• Entrances to all museums and sites included in the trip itinerary
• Guided tour of the Basilica of Assisi
• Guided walking tour Città della Pieve
• Hot air balloon ride in Tuscany (optional)
• Private visit of active archeological site
• Entrance to the thermal, mineral pools of Fonteverde Spa
• Walk along the Via Romea pilgrimage trail (rated easy)
• Walk in Sacro Bosco di San Francesco (rated easy)
• Walk to archeological site San Casciano dei Bagni (rated easy, but steep going downhill)
• Daily accompaniment with Strada Toscana’s guides and trip leaders
• Free time for shopping and exploring on your own

Walking and Mobility Note: This journey includes walking on uneven terrain, cobblestones, steps, and occasional steep areas in historic and countryside environments. While the pace is relaxed and not considered hiking, guests must be steady on their feet and able to walk independently without mobility aids or personal assistance.

Not included: Airfare, meals, alcoholic drinks, buses, trains or boat transportation outside of that which is specifically listed in the trip package, gratuities for villa staff and drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. The quality of the trip is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.

DATES & DETAILS

• Dates: November 1-6, 2026
• Trip Price: $3,895 USD – $4,595 USD (select room type upon booking)
• Room Descriptions:
  • Classic: Single occupancy, double bed, private ensuite bathroom
  • Superior: Single or double occupancy, double bed, private ensuite bathroom
  • Deluxe: Double or twin occupancy, 1 double bed or 2 singles, private ensuite bathroom
• $700 deposit is required to secure your space on this tour
• Terms and Conditions

BOOK NOW