Experience small-town Italy like a local on our slowcation… Tuscany conjures up dreams of life at a slower pace where you can soak in the Italian countryside's culture, food, and picturesque vistas. Stroll through narrow passageways of medieval villages perched on hilltops. Pick out cheese & wine at the market in town and chat with the locals. Tuscany is the dream vacation and now is your chance to go!

Live like a local: Skip the hoards of tourists in Italy's more popular towns and cities and live the good life in a true Italian village with barely any tourists. If you want to experience the real Italy, this is your trip!

Ideal location: This villa was converted into a hotel in the early 1900s and is situated right in town making it easy to explore. A cafe, grocery store, and many restaurants are just a few steps away from your accommodation. 

Discover Italy: Many of Tuscany & Umbria’s most famous towns are only 30 - 45 minutes away from the hotel so you can explore all the best locations in the region without going far. 

Welcome to Italy! Transport to your hotel in the hills of Umbria is included.* Upon arrival, you can enjoy some welcome drinks and hors d’oeuvres. You have the rest of the day to explore the charming town of Città della Pieve right outside your doorstep or take a dip in the pool. Later, enjoy a welcome dinner at the hotel as you get to know your fellow travelers.

*IMPORTANT: Airport pick-up from Rome (FCO) is included only if you arrive on Day 1 or are staying in Rome before the trip. Pick-up on other dates or from other cities is not included. We normally don’t include transfers, but this trip is an exception since Città della Pieve is far.

Airport drop-off is not included. Please budget accordingly. Your slowcation leader can help arrange departure transportation and here are the two options:

1.) Private transfer: Shareable with others departing at similar times, €400~€450 per vehicle, payable in cash to the driver.

2.) Taxi + train: Taxi to Chiusi €25~€35 (usually payable by card) + train to Rome €30~€50 (tickets can be purchased online with a card).

Included :

• Transfers: Rome – Città della Pieve by private transport (approximately 2 hours)

• Activities: Welcome drink & hors d’oeuvres; Welcome dinner

• Meals: Dinner

• Accommodation: Historic boutique hotel

Start the day with a walking tour of Città della Pieve with a local guide who will show you the main sights, point out essential services like shops, cafés, banks, pharmacies, and post offices, and share stories about the town’s rich history. Città della Pieve is renowned for its long tradition of saffron cultivation, also known as “red gold.” We'll have the chance to learn all about this tradition at the Saffron Museum, where you'll also enjoy a saffron tasting!

Enjoy lunch featuring one of Umbria’s most celebrated dishes: pici cacio e pepe, hand-rolled pasta tossed in a giant wheel of cheese until it reaches a rich, creamy perfection.

The rest of the afternoon is free to explore this charming town and perhaps enjoy your first passeggiata — a leisurely stroll after lunch to digest and soak in the atmosphere. Along the way, you’ll see why Città della Pieve won the Pio Alferano Prize as Italy’s “perfect city,” admired for its beauty, art, and relaxed charm.

Included :

• Activities: Citta della Pieve walking tour; Saffron tasting; Free time

• Meals: Breakfast, Lunch

• Accommodation: Historic boutique hotel

Start your day with a hands-on cooking class in a countryside villa surrounded by olive trees and vineyards. A local chef will teach you the secrets of authentic Umrian cooking as you prepare a few regional dishes. After the class, enjoy the fruits of your labor with a glass of local wine.

In the afternoon, head to Orvieto, a hill town set on a plateau of golden stone with wide views over the valley. You might visit the striking Duomo, explore the ancient Etruscan caves beneath the city, or descend into St. Patrick’s Well. Or you can just wander the quiet streets, browse small shops, and pop a squat at a local cafe with a coffee or glass of Orvieto Classico in the main square.

Included :

• Activities: Cooking class; Orvieto free time

• Meals: Breakfast, Lunch

• Accommodation: Historic boutique hotel

Head to Tuscany and make your way to the hilltop town of Montepulciano, famous for its wines. Enjoy some free time wandering its medieval streets and taking in the panoramic views of vineyards and rolling countryside.

Next, visit a nearby historic winery that’s been family-run for generations and is now led by a team of passionate women winemakers. The estate is known for its traditional methods, hand-harvested grapes, and centuries-old cellars where wines age naturally in oak barrels. Enjoy a tour of the property, a guided tasting of its renowned Vino Nobile Montepulciano wines, and a leisurely lunch featuring local specialties.

Afterward, continue to Pienza, a graceful Renaissance town overlooking the Orcia Valley. Often called the “ideal city” thanks to Pope Pius II, it’s a lovely place to wander cobblestone streets, browse small shops, and sample the town’s famous pecorino cheese.

Included :

• Activities: Montepulciano free time; Winery tour & tasting; Pienza free time

• Meals: Breakfast, Lunch

• Accommodation: Historic boutique hotel

Today is a free day for you to enjoy as you wish. You might spend your time wandering through the medieval streets of Città della Pieve, discovering its historic charm and local treasures. Or perhaps you’ll feel like exploring the surrounding gems of Tuscany and Umbria, with a visit to the Renaissance wonders of Florence or the captivating medieval city of Siena.

Your host can offer advice on public transportation and assist you with booking private transportation with sufficient notice. Remember that this is a semi-independent trip, therefore, you’re free to make your own plans.

Activities: Free day

• Meals: Breakfast

• Accommodation: Historic boutique hotel

Get ready for an experience far away from the main tourist attractions. Travel along the winding roads of Val d'Orcia where some of Italy's best pecorino cheese is produced. Surrounded by towering cypress trees and rolling hills stretching toward the blue sky, Val d'Orcia is straight from a postcard!

Spend the day in the heart of the Tuscan countryside with Giancarlo and his brother, the owners of a family sheep and cheese farm. They will share their passion for nature and the secrets of pecorino cheese with you. Learn about how they work the land, raise the animals, and produce cheese as you see, smell, and taste this family's everyday life over the generations. Not only will you participate in one of the best cheese tastings in Italy, but their infectious enthusiasm will guarantee you leave with a smile on your face!

Included :

• Activities: Sheep farm tour; Cheese making demonstration; Cheese and wine tasting
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Make your way to Assisi which many of our past travelers have said is their favorite town in all of Italy! Assisi is a hilltop town in the beautiful region of Umbria with charming lanes, massive gates, and stone buildings. The town is famous as the birthplace of St. Francis of Assisi, one of Italy’s most venerated saints, and has attracted pilgrims from all over the world for over 700 years. The Basilica of Saint Francis was built in his honor right after his death and is covered in some of the best-preserved frescoes in all of Italy. After lunch, enjoy some free time to explore. Be on the lookout for unique jewels inspired by Saint Francis that are only made in Assisi.

Included :

• Activities: Assisi tour; Basilica of Saint Francis; Assisi free time
• Meals: Breakfast, Lunch
• Accommodation: Historic boutique hotel

Spend the morning at an innovative farm in the Umbrian countryside where you’ll see how food is grown, harvested, and brought to the table. You’ll learn about biomimic farming and what it takes to run one of the most biodiverse farms in Europe. After the tour, enjoy a fresh, seasonal brunch with wine right in the vineyard. The rest of the afternoon is yours to relax or explore at your own pace.

Included:

• Activities: Farm visit & brunch
• Meals: Breakfast, Brunch
• Accommodation: Historic boutique hotel

Your last day is all yours to enjoy. Maybe you’ll tick off one more town from your bucket list, or perhaps you’ll embrace Italy’s famous ‘Il dolce far niente’—the sweet art of doing nothing—and simply linger in a coffee shop in Città della Pieve, your home for the past 8 days.

In the evening, we’ll come together at the hotel for a festive farewell dinner, Italian style, to toast the memories of your journey!

Included :

• Activities: Free days

• Meals: Breakfast, Farewell dinner

• Accommodation: Historic boutique hotel

Say farewell to Italy and your new friends. Today is the last day of your trip. We hope to see you on one of our next adventures!

*IMPORTANT: Airport drop-off is not included. Please budget accordingly. Your slowcation leader can help arrange departure transportation and here are the two options:

1.) Private transfer: Shareable with others departing at similar times, €400~€450 per vehicle, payable in cash to the driver.

2.) Taxi + train: Taxi to Chiusi €25~€35 (usually payable by card) + train to Rome €30~€50 (tickets can be purchased online with a card).

Included :

• Activities: Free time; Departure (at your own expense)

• Meals: Breakfast

*Itinerary is subject to change.