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: 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 3: Orvieto

  • Highlights: Excursion to Orvieto, Christmas village market, winery tour & tasting
  • Breakfast, 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 gather at a local cafe for apericena (aperitivo + light dinner).

DAY 4: Città della Pieve

  • Highlights: Churches tour, tortellini-making class, pizza night
  • Breakfast, lunch, dinner

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.

This afternoon, after some free time, you’ll have the opportunity to explore and shop the local boutiques and shops along the town’s charming main avenue. This evening we’ll gather together at a private home for aperitivo, followed by pizza night at a cozy, wood-fired pizzeria.

DAY 5: Montepulciano

  • Highlights: Hot chocolate & panettone, excursion to Montepulciano
  • Breakfast, dinner

This morning, after a leisurely breakfast, and perhaps an invigorating walk, we’ll walk to our friends’ 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 – including the famous Dolce & Gabbana pistacchio. Afterwards, you’ll have free time to explore and enjoy lunch on your own.

This afternoon we travel to the picturesque town of Montepulciano, perched on a scenic hilltop surrounded by silvery olive groves and sweeping vineyards that produce the world renowned Vino Nobile di Montepulciano. Here you’ll enjoy a brief tour in Piazza Grande, followed by free time to shop and explore on your own. Afterwards we’ll meet up at a local trattoria for a delicious, Tuscan-style dinner.

DAY 6: Monteleone

  • Highlights: Market day, visit to olive press, olive oil tasting
  • Breakfast, lunch, dinner

This morning the local market is in town, so you might have an early breakfast and then venture out to browse the many stands. In late morning we’re off to the village Monteleone and our friends’ family-owned frantoio (olive press). Here’s you’ll take a tour of the facility and watch as bins of local olives are cleaned, washed and pressed into extra virgin olive oil. Next we’ll gather near the fireplace in the tasting room for toasted bread drizzled with new oil – the classic bruschetta – accompanied by new wine. A true local experience.

Lunch today is served up at our friends’ inviting cafe, followed by free time. In late afternoon we gather together with Francesca, a delightful, local pastry chef, to design and decorate your own dessert for this evening. A celebratory aperitivo accompanies this fun lesson, followed by a special farewell dinner prepared by Chef Jordy.

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 and wine tasting
  • Hot chocolate and panettone tasting
  • Tour of organic, ancient-grains mill
  • Visits to Christmas markets
  • Torta decorating lesson
  • 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

BOOK NOW

(this tour is offered by host invitation only)