Itinerary
- Day 1
Rome to Città della Pieve
You'll arrive in Italy and transfer to your hotel nestled in the hills of Umbria. After settling in, there's time for welcome drinks and hors d'oeuvres to kick things off. If you're interested, walk through the charming town of Città della Pieve or hang out by the pool and relax. Later in the evening, join the group for a welcome dinner at the hotel.
- Meals
- Dinner (Welcome dinner at the hotel)
Included Activities
- Welcome drink and hors d'oeuvres
- Welcome dinner
- Explore Città della Pieve
Optional Activities
- Swimming in hotel pool
Landmarks/POIs Città della Pieve - Day 2
Città della Pieve
Start your morning with a guided walking tour of Città della Pieve where you'll learn about the town's services and its rich history. Stop at the Saffron Museum to taste local saffron and find out why it matters culturally. Lunch features traditional pici cacio e pepe. The afternoon is free so you can wander the charming streets, do some shopping, or take a leisurely passeggiata through town.
- Meals
- Breakfast, Lunch (Pici cacio e pepe, hand-rolled pasta tossed in a giant wheel of cheese)
Included Activities
- Città della Pieve walking tour with local guide
- Saffron Museum visit and tasting
- Free time to explore
Landmarks/POIs Saffron Museum Città della Pieve - Day 3
Orvieto
Head to a countryside villa surrounded by olive trees and vineyards for a hands-on cooking class with a local chef. You'll prepare regional Umbrian dishes and then eat what you've made with local wine. After lunch, travel to Orvieto where the afternoon is yours. Check out the striking Duomo, explore ancient Etruscan caves, descend into St. Patrick's Well, or simply browse the shops and relax in the main square.
- Meals
- Breakfast, Lunch (Lunch featuring regional Umbrian dishes and local wine from the cooking class)
Included Activities
- Cooking class in countryside villa
- Orvieto free time
Optional Activities
- Visit Orvieto Duomo
- Explore ancient Etruscan caves
- Descend into St. Patrick's Well
Landmarks/POIs Orvieto Orvieto Duomo St. Patrick's Well - Day 4
Pienza
Travel to Tuscany and walk through the medieval hilltop town of Montepulciano with its panoramic views over vineyards and rolling countryside. Visit a family-run historic winery led by women winemakers, tour the centuries-old cellars, and taste Vino Nobile Montepulciano wines. Enjoy a leisurely lunch with local specialties. Later, head to Pienza, a graceful Renaissance town overlooking the Orcia Valley, where you can wander cobblestone streets, browse shops, and sample famous pecorino cheese.
- Meals
- Breakfast, Lunch (Leisurely lunch at the winery featuring local specialties and Vino Nobile Montepulciano wines)
Included Activities
- Montepulciano free time
- Winery tour and guided tasting
- Pienza free time
Landmarks/POIs Montepulciano Pienza - Day 5
Free Day
This day is completely free to explore as you wish. Wander the medieval streets of Città della Pieve, or venture out to discover other parts of Tuscany and Umbria like Florence or Siena. Your host can advise on public transportation and arrange private transportation if you give advance notice.
- Meals
- Breakfast
Optional Activities
- Explore Città della Pieve
- Visit Florence
- Visit Siena
- Explore surrounding Tuscany and Umbria
Landmarks/POIs Città della Pieve Florence Siena - Day 6
Val d'Orcia Sheep Farm
Travel through the Val d'Orcia with its towering cypress trees and rolling hills. Spend the day at a family sheep and cheese farm with owners Giancarlo and his brother, learning about their passion for raising animals and producing pecorino cheese. Participate in a cheese-making demonstration and have one of Italy's best cheese tastings paired with wine.
- Meals
- Breakfast, Lunch (Lunch at the family sheep and cheese farm)
Included Activities
- Sheep farm tour
- Cheese-making demonstration
- Cheese and wine tasting
Landmarks/POIs Val d'Orcia - Day 7
Assisi
Travel to Assisi, the hilltop town known as the birthplace of St. Francis of Assisi. Explore charming lanes, massive gates, and stone buildings while taking in the town's spiritual history. Visit the Basilica of Saint Francis with its beautifully preserved frescoes, then grab lunch. Spend the afternoon wandering the town and discovering unique items made only in Assisi that are inspired by Saint Francis.
- Meals
- Breakfast, Lunch
Included Activities
- Assisi town tour
- Basilica of Saint Francis visit
- Assisi free time
Landmarks/POIs Assisi Basilica of Saint Francis - Day 8
Umbrian Farm Visit
Spend your morning at an innovative farm in the Umbrian countryside learning about biomimic farming and the biodiversity practices of one of Europe's most biodiverse farms. See how food is grown, harvested, and brought to the table. Enjoy a fresh, seasonal brunch with wine in the vineyard, then spend the rest of the afternoon relaxing or exploring at your own pace.
- Meals
- Breakfast, Brunch (Fresh, seasonal brunch with wine in the vineyard)
Included Activities
- Farm visit and biomimic farming tour
- Farm brunch with wine
- Day 9
Farewell Dinner
Your final day is yours to enjoy. Tick off one more town from your bucket list or embrace Italy's 'il dolce far niente' and linger in a coffee shop in Città della Pieve. In the evening, gather together at the hotel for a festive farewell dinner to toast the memories of your journey.
- Meals
- Breakfast, Dinner (Festive farewell dinner at the hotel)
Included Activities
- Farewell dinner
Optional Activities
- Explore additional towns
- Leisure time in Città della Pieve
Landmarks/POIs Città della Pieve - Day 10
Departure
Say farewell to Italy and your new friends. Today marks your final day of the trip.
- Meals
- Breakfast
Optional Activities
- Departure arrangements
