Private Winter Tour

THE HOLIDAY SEASON in Italia

Christmas markets, artisan panettone, hot chocolate, decorated piazzas, newly pressed olive oil, mulled wine, crackling fires, spectacular vistas, roasted chestnuts, tortellini in brodo…December in Italy evokes memories of simple traditions, gatherings with friends and delectable, seasonal foods. Plus, this beautiful time of year is made even more magical when experienced in medieval villages and old-fashioned markets.

RICH WITH Experiences

We’ve created this trip to be rich with experiences that are not only authentic, but also ideal for those who enjoy travel, fun activities and exploration, along with creating a fellowship with like-minded travelers. From medieval villages to countryside churches to family-owned wineries, you can expect daily experiences that bring you up-close to the local culture.

Each day, on this active, seasonal itinerary, you can also expect to walk. Our walks range from easy/leisure to moderate, and you’ll encounter hard cobblestones, uneven pavement, steps and steep hills. We do caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience the rest of the group.

ITINERARY

DAY 1: Arrival

  • Highlights: Arrival and welcome
  • Dinner

Benvenuti in Italia! Upon your arrival at Rome Fiumicino Airport, our private drivers will transport you to the Italian countryside, and your boutique hotel accommodations in the unspoiled village of Città della Pieve. After check in, you’ll enjoy a walking tour of the historic center of the village and its three medieval neighborhoods, followed by a seasonally-inspired dinner prepared by the talented Chef Jordy.

DAY 2: Orvieto

  • Highlights: Excursion to Orvieto, winery tour & tasting
  • Breakfast, lunch, dinner

This morning, after breakfast, we make our way to the hill town of Orvieto, perched on a panoramic bluff that overlooks the Val d’Chiana. First stop is the town’s magnificent duomo that boasts some of the most beautifully preserved frescoes in Italy. Afterwards you’ll have the opportunity to explore Orvieto on your own with its winding alleyways, excellent museums and inviting shops (the majolica ceramics are amazing!)

Lunch today is on your own (we’ll have recommendations), before we meet up to make our way to our friend, Enrico’s, wine cantina with its spectacular views of rolling hills and vineyards. After a tour of the historic wine cantina, and a chance to photograph the stunning panoramas, you’ll enjoy a wine tasting, accompanied by local products and cheeses. Afterwards we’ll head back to Città della Pieve for some free time. This evening we’ll enjoy a beautiful, fireside dinner at a local trattoria.

DAY 3: Città della Pieve

  • Highlights: Churches tour, tortellini-making class, hot chocolate & panettone tasting
  • Breakfast, lunch

This morning, after breakfast, you’ll step back in time as we explore some of Città della Pieve’s fascinating churches with medieval frescoes and Renaissance masterpieces. Then it’s off to our friend, Cristian’s, bistro for a delightful tortellini-making class, that includes a tour of Cristian’s wine cantina. Afterwards you’ll enjoy lunch featuring your hand-made “tortellini in brodo” – a traditional Christmas pasta dish from this part of Italy.

Afterwards you’ll have time to explore and shop the local boutiques and shops along the town’s charming main avenue, or simply rest and recharge. In late afternoon, we head to our friend, Stefania’s inviting cafe for hot chocolate and panettone – a seasonal tradition that can’t be missed. After choosing your favorite flavor of European-style hot chocolate (gianduia and dark chocolate orange are always favorites) you’ll sample panettone from some of Italy’s prized pasticcerie – the perfect dessert after a long lunch.

DAY 4: Pienza

  • Highlights: Excursion to Pienza, visit to organic grain mill, cheese tasting
  • Breakfast, lunch, aperitivo

This morning, after breakfast, our drivers will transport you to the Renaissance hill town of Pienza, situated in one of the most photographed areas in Tuscany, where you’ll take a walk along the town’s “passeggiata” lane, with sweeping views of the Val d’Orcia. Once inside the historic center you’ll have some free time to explore and shop on your own. The beautiful duomo is a must-see, along with irresistible artisan shops. Afterwards we’ll continue to the nearby Mulino Val d’Orcia, an organic, ancient grains mill that produces stone-ground flours, along with pastas and breads. Here you’ll enjoy delightful tour of the mill with our friend, Amedeo, followed by a delicious, organic lunch served in the mill’s cozy restaurant – featuring their exceptional pasta.

In the afternoon we’ll return to Città della Pieve where you’ll have free time to rest, relax or perhaps take a walk through the village. This evening we’ll gather at a local enoteca for a private cheese tasting that includes exceptional pecorino cheese from Pienza – including pear, rosemary and truffle – along with a selection of local wines.

DAY 5: Montepulciano

  • Highlights: Excursion to Montepulciano, Christmas market
  • Breakfast, lunch, dinner

This morning, after breakfast, we’ll set out for the hilltop town of Montepulciano, a jewel of southern Tuscany surrounded by silvery olive groves and the rolling vineyards that produce the celebrated Vino Nobile di Montepulciano. As we make our way up the winding main street, you’ll have time to browse the artisan shops, sample local treats, and soak in the festive atmosphere at your own pace.

For lunch, we’ll gather at the historic Caffè Poliziano, an elegant Art Nouveau landmark overlooking the valley below. Here we’ll enjoy a leisurely meal featuring hearty Tuscan soup and regional specialties that capture the flavor of the season.

After lunch, we’ll stroll to Piazza Grande, where the annual Christmas Market fills the square with charming wooden stalls, handmade gifts, and the scent of mulled wine—an enchanting way to experience Montepulciano in winter. This evening, back in Città della Pieve, we’ll enjoy a cozy apericena (apertivo + light dinner) at a local cafe.

DAY 6: Parrano

  • Highlights: Market day, visit to Parrano, farmhouse dinner + olive oil tasting
  • Breakfast, dinner

On our final day together, you’ll have the morning free to shop the Christmas market in Città della Pieve, where the narrow streets are lined with festive stalls and local artisans selling handmade gifts and holiday treats. Later in the morning, we’ll join a local historian for a guided visit of the town’s Duomo and museum, discovering layers of history and art that tell the story of this remarkable hilltop village.

After lunch on your own, we’ll set off for the nearby village of Parrano, where a short walk around its medieval castle offers lovely views and a glimpse of quiet village life. From there, we’ll continue to our friend Francesca’s farmhouse restaurant, where we’ll enjoy an olive oil tasting followed by a farewell dinner featuring seasonal recipes inspired by the Christmas season — a warm and flavorful way to close our journey together.

DAY 7: Departure 

Early morning departure for Rome Fiumicino Airport

WHAT’S INCLUDED

  • 7 days/6 nights at Boutique Hotel Vannucci (all sleeping rooms feature ensuite, marble bathrooms)
  • No single supplement fee
  • Private group transportation to/from Rome Fiumicino Airport on arrival and departure dates
  • Private ground transportation to/from all locations included in the itinerary
  • All abundant buffet breakfasts featuring made-to-order Italian coffee or tea
  • 3 lunches at hand-selected cafes and trattorie
  • 5 regionally inspired dinners
  • Wine at lunches and dinners
  • Daily accompaniment by members of team Strada Toscana
  • Private, guided walks and tours
  • Hands-on tortellini-making lesson
  • Winery tour & wine tasting
  • Hot chocolate and panettone tasting
  • Tour of organic, ancient-grains mill
  • Visits to Christmas markets
  • Wine & pecorino cheese tasting
  • Olive oil tasting
  • Free time to explore and shop on your own

Not included: Airfare, transportation and meals outside of that which is specifically listed in the trip package, gratuities for hotel staff and drivers.

ACCOMMODATIONS Boutique Hotel Vannucci 

Hotel Vannucci began as a project of Vittoria Spinola, daughter of King Vittorio Emanuele II, who fled Pisa (and an arranged marriage with her elderly husband) to start a new life with her lover in Città della Pieve. Here, she and her soon-to-be new husband, Paolo, built two villas that became luxurious holiday accommodations for wealthy Romans vacationing in the countryside. In 1903 one of the villas became Hotel Vannucci, and today it maintains the elegance and refinement of its inception, with luxurious sleeping rooms, marble bathrooms and inviting gardens. A stay here is truly special, nestled just outside the medieval walls of the historic, and unspoiled, village of Città della Pieve.

DATES & DETAILS

  • Dates:
    • December 8-14, 2025
  • Trip Price: $3,295 – $3,795 (choose room type upon booking)
  • Room Descriptions:
    • Single: Single occupancy, single bed, private ensuite bathroom
    • Classic: Single occupancy, double bed, private ensuite bathroom with walk-in shower
    • Superior: Single occupancy, double bed, private ensuite bathroom with tub/shower combination
    • Deluxe: Double occupancy, double bed or two singles, private ensuite bathroom with separate tub and shower (for friends traveling together)
  • $700 deposit is required to book your space on this tour
  • No single supplement fee
  • Terms and Conditions

SOLD OUT

(this tour is offered by host invitation only)