Tuscany Castles, Villas and Gardens, September 5-10, 2020

Click or swipe to view the slideshow below!

Open the Door to an Insider’s View 

For those who long for a deeper, insider look at some of the most romantic – and historic – villas, gardens and castles in Italy, this tour is truly a dream come true!

Each day, be ready to explore a medieval castle, or tour a Renaissance villa, or stroll a manicured garden. These are the structures and spaces that reflect Italy’s aristocratic past – each with its own intriguing history and particular beauty. From the medieval ramparts of La Fortezza di Castiglione to the frescoed rooms of Villa Farnese to the panoramic gardens of Villa la Foce.

Step back into history and live as Italy’s families of nobility once did, with lavish dining halls and lush gardens – often protected by a fortified castle. See firsthand the progression from fortressed medieval villages to stately countryside villas, and learn about the incredibly talented architects and artists who made it all a reality.

Stunningly Beautiful and Endlessly Fascinating

  • Antique collections in family-owned castles
  • Stunning frescos along winding corridors
  • Intimate lunches in grand dining halls
  • Estate wine tastings in centuries-old cantinas
  • Evocative medieval passageways
  • Elaborately decorated salons
  • Renaissance fountains
  • Romantic hidden gardens
  • Regal balconies with breathtaking views
  • Historic battlements with crenellated towers
  • Carved porticos with coats of arms
  • Intriguing sculpture parks
  • Private chapels
  • Family secrets
  • Citrus-filled limonaria
  • Manicured box hedges
  • Vine-covered pergolas and gazebos
  • Enchanting histories
  • Secret passageways


Saturday, September 5: Arrival

  • Tour of Villa Poggio alla Trese, trip orientation
  • Dinner

Benvenuti in Italia! Upon arrival at Rome Fiumicino Airport, sit back and relax as you are transported by private van service to the Italian countryside and Poggio alla Trese, your 17th century villa accommodations near the Tuscan town of Chiusi. After check-in you’ll have the opportunity to explore your surroundings and learn some of the fascinating history of the both the house and the area. Then it’s time for a friendly aperitivo before enjoying a delicious, regional-style dinner.

Sunday, September 6: Siena Environs

  • Villa di Geggiano, Vico Bello Gardens
  • Breakfast, lunch and dinner

This morning, after a breakfast at the villa that includes freshly baked breads and torte from the local pasticceria, sheeps’ milk yogurt, fresh fruits & cheeses, organic honeys and marmalades, along with a variety of Italian coffees and teas, you’ll be heading through the rolling hills of Tuscany to the countryside in the Siena province where you’ll find elegant Villa di Geggiano. The villa was given to the Bianchi Bandinelli family as the dowry of Girolama Santi when she married Girolamo Bandinelli in 1527. Its majestic appearance today, including its 18th century furniture and decorations, is the result of radical rebuilding and restoration by various families throughout its history. Here you’ll enjoy a private, guided tour of its richly decorated rooms, along with the villa’s formal gardens. Afterwards it’s time for an al fresco lunch, featuring wines from the estate. 

In afternoon we’ll continue to the gardens of Villa Vicobello to discover a splendid example of a Renaissance park and Italian garden. Enjoy the magic of this historic place while learning the fascinating history of the Chigi family – owners of the villa since 1500. After returning to the villa in late afternoon, you’ll enjoy time with your fellow travelers to reflect on the day during aperitivo. Dinner follows, served up on the south terrace, under the stars.

Monday, September 7: Sarteano, Pienza, Val d’Orcia

  • Castello di Sarteano, Palazzo Piccolomini, La Foce Gardens
  • Breakfast and dinner

This morning you’ll enjoy an abundant breakfast before heading to the ancient hill town of Sarteano, where you’ll visit one of the region’s most intact, and beautifully constructed castles, dating back to at least 1038. Talk about medieval! Walk over the drawbridge, that spans the now-dry moat, to enter the impressive, fortressed doorway, from which you’ll explore the narrow medieval passages and stairways. Then we continue to the spectacular Val d’Orcia and the Renaissance treasure, Pienza, to enjoy an eye-opening tour of the frescoed palazzo of Pope Piccolomini with its manicured gardens, overlooking the valley below.

Lunch is on your own, at any one of Pienza’s charming trattorie, followed by time on your own for exploring or picture-taking. In afternoon we head to Tuscany’s historic Villa La Foce. Here you’ll take a guided tour through the famed gardens of Iris Origo (1902-1988), an Anglo-American biographer and historian of international fame, whose spellbinding story of perseverance and creativity will captivate you. Afterwards, it’s back to the villa for a relaxing aperitivo, followed by a special farewell dinner. 

Tuesday, September 8: Caprarola, Mugnano, Bomarzo

  • Guided tour of Villa Farnese Caprarola, lunch at Castello di Mugnano, Park of the Monsters Bomarzo
  • Breakfast, lunch and dinner

After another delicious breakfast at the villa, we head south to the hill town of Caprarola, situated in the region of Lazio, just outside of the southern stretches of Tuscany. One of Italy’s best-kept secrets lies here, the elegant Villa Farnese with its incredible architecture and stunning frescoed rooms. Here you’ll enjoy a private guided tour that leads from one room to another, each more beautifully painted than the last – including the famous room of maps, dated to the 15th century. Next, head outside for a stroll of the sweeping gardens!

Afterwards, it’s off to nearby Castello di Mugnano, where our friends will treat you to a delicious lunch served up in their castle’s private rooms. Then we’ll take in the views from the castle’s fabulous loggia before heading off to Bomarzo’s evocative Park of the Monsters. Wander among the colossal, whimsical sculptures spread throughout the park – including the curious leaning house. It’s like a crazy, 15th century amusement park! Afterwards, you’ll head back to the villa to relax, enjoy an aperitivo with your fellow travelers, and of course a delectable dinner.

Wednesday, September 9: Parrano, Montegiove

  • Caffè in a private villa, Castello di Parrano, Castello di Montegiove
  • Breakfast, lunch and dinner

This morning, after breakfast at the villa, you’re invited to tour a private home, and perhaps enjoy a second caffè, as you learn about the restoration and construction of Italy’s striking countryside casale. Then it’s off to the beautifully preserved castle village of Parrano, boasting one of the most imposing and impressive private castles of the region. Enjoy an invitation-only tour that includes the Pope’s staircase, as well as the castle’s grotto of thermal springs. Afterwards, we continue to striking Montegiove – tucked into the green hills of Umbria – where our friend, the Marquis, will give you a private tour of his 12th century castle – including his medieval cantina. Talk about special! Then make yourself at home for a private wine tasting, along with a light lunch, featuring the estate’s excellent wines.

In afternoon we head back to the villa for some time on your own to relax and refresh before enjoying a final aperitivo together, followed by an elegant farewell dinner.

Thursday, September 10: Departure

Our drivers will be transporting you this morning to Rome Fiumicino Airport.


Tuscany Castles, Villas and Gardens

  • 6 Days/5 Nights
  • Dates:
    • September 5-10, 2020
    • A $500 deposit is required to book your space on this trip. See terms.
  • Trip Price (choose your room configuration upon booking):
    • $2,900 USD per person – single occupancy room with ensuite bathroom
    • $2,800 USD per person – single occupancy room with shared bathroom (no more than 2 people per bathroom)
    • $2,600 USD per person – double occupancy room (1 double or 2 single beds) with ensuite bath. Note: This room configuration is intended for couples or two friends/siblings traveling together.



Your accommodations are beautiful Poggio alle Trese, a 17th century villa, nestled along the border of Tuscany and Umbria, near the town of Chiusi (Tuscany). The villa boasts number living rooms, sweeping terraces for dining or lounging, swimming pool, elegant breakfast room and grand dining hall. Sleeping rooms are furnished with family antiques are offer either an ensuite bathroom or shared bathroom (max 2 guests per bathroom). Rooms options are made available upon booking. View photos of Villa Poggio alle Trese here. 


  • 6 days/5 nights at elegant Villa Poggio alla Trese, situated in the picturesque countryside near the charming Tuscan hill town of Chiusi.
  • Group transportation by private van service to/from Rome Fiumicino Airport on arrival and departure dates. Please note that although group transportation is only provided to/from the airport in Rome, some of our guests choose to extend their stay in Italy before and/or after the retreat. After you’ve registered, we’re happy to provide contact information for our favorite hotels in Florence, Rome and Venice – as well as a link to book train tickets.
  • Private van service to/from all cities, towns and sites included in the itinerary
  • All abundant breakfasts, featuring fresh-baked Tuscan pastries, organic sheeps’ milk yogurt, local cheeses, seasonal fruits, organic cereal and fresh eggs plus Italian caffè, cappuccino and herbal teas.
  • 3 lunches  
  • All regionally inspired dinners with local wines 
  • Insider access
  • Entrance fees
  • Guided tours
  • Wine tastings
  • Time on your own for shopping and exploring
  • Evening aperitivo hour for chatting, sharing and relaxing

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.


Castles, Villas and Gardens of Italy

  • 6 Days/5 Nights
  • Dates:
    • September 5-10, 2020
    • A $500 deposit is required to book your space on this trip. See terms.
  • Trip Price (choose your room configuration upon booking):
    • $2,900 USD per person – single occupancy room with ensuite bathroom
    • $2,800 USD per person – single occupancy room with shared bathroom (no more than 2 people per bathroom)
    • $2,600 USD per person – double occupancy room (1 double or 2 single beds) with ensuite bath. Note: This room configuration is intended for couples or two friends/siblings traveling together.