Journey through Umbria and Tuscany: medieval villages, wine tastings, olive oil, ceramics, cooking classes, and iconic towns. This immersive tour blends history, flavors, and authentic Italian culture.
Starting from $.
Small gems of Umbria and Tuscany Tour
8 Days/7 Nights
Starting from
$
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
BETTONA
Where The Trip Begins In Quiet Stone Streets
- Arrival in Bettona, a medieval village in the heart of Umbria
- Check-in at your hotel accommodation
- Welcome dinner in a characteristic local restaurant
- Overnight stay in Bettona
Day 2
TORGIANO, DERUTA, PERUGIA
From Museum Views To City Stroll
- Breakfast at the hotel in Bettona
- Depart for Torgiano, hilltop town near Bettona
- Visit the Wine Museum at leisure
- Wine tasting at Cantine Giorgio Lungarotti near Torgiano
- Afternoon in Deruta, famous for ceramics and pottery
- Suggested visit: National Museum of Pottery in Deruta’s center
- Stop in Perugia for a stroll and chocolate tasting opportunities (home of Bacio)
- Dinner on your own and overnight stay
Day 3
MONTEFALCO, ASSISI
A Day For Panoramas and Pilgrimage Atmosphere
- Breakfast at the hotel in Bettona
- Depart for Montefalco, “the terrace of Umbria”
- Visit an ancient olive oil mill run by a local family
- Tasting of traditional local food and olive oil with Italian snacks
- Afternoon at leisure in Assisi
- Suggested visits: Basilica of St. Francis and historic center
- Dinner on your own
- Return to Bettona for overnight stay
Day 4
MONTEPULCIANO, PIENZA, SIENA
From Umbria’s Charm To Tuscany’s Famous Hills
- Breakfast and check-out from your hotel in Bettona
- Drive towards Tuscany
- First stop: Montepulciano, Renaissance hill town and birthplace of Poliziano
- Wine tasting with snacks and cellar tour in an ancient wine cellar in the center
- Lunch at leisure
- Afternoon stop in Pienza, with time to wander its romantic narrow streets (e.g. Via dell’Amore)
- Arrival at your hotel in the Siena area (Siena or Monteriggioni)
- Dinner on your own and overnight stay
Day 5
TUSCAN COOKING CLASS, SAN GIMIGNANO
From Countryside Kitchen To Walled Town Wandering
- Breakfast at the hotel in the Siena area
- Drive into the Sienese countryside for a cooking class in a farmhouse
- Learn the basics of Italian cuisine (including fresh pasta making)
- Lunch featuring the dishes prepared during the class
- Afternoon visit to San Gimignano
- Free time to wander among the towers, shops, and medieval streets
- Dinner on your own and overnight stay at your hotel
Day 6
CHIANTI REGION, SIENA
Vineyard Morning, Medieval City Afternoon
- Breakfast at the hotel
- Depart for the Chianti region between Siena and Florence
- Discover small hamlets and villages in the wine country
- Visit a local winery for an estate tour and wine tasting
- Afternoon in Siena for independent exploration
- Time to wander medieval streets, shop, and relax in Piazza del Campo
- Dinner on your own and overnight stay at your hotel
Day 7
MONTALCINO
A Day That Ends Back With Wine Notes
- Breakfast at the hotel
- Depart for Montalcino, home of Brunello di Montalcino
- Winery tour and tasting at a Brunello estate
- Lunch in a central trattoria in Montalcino
- Suggested afternoon visit to the 11th‑century Romanesque church of Sant’Antimo
- Stop at the Benedictine Abbey of Monte Oliveto Maggiore on the way back
- Return to Siena area
- Dinner on your own and overnight stay
Day 8
MONTERIGGIONI or SIENA
From Rolling Hills To Real Life
- Breakfast at the hotel
- Check-out and end of services
- Suggested: visit Florence or extend your stay there for a few more days
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
BETTONA
Where The Trip Begins In Quiet Stone Streets
Arrive in Bettona, a lovely medieval hilltop village surrounded by the green landscapes of Umbria. Check in at your hotel and enjoy a welcome dinner in a characteristic restaurant, where you’ll be introduced to traditional Umbrian flavors. Overnight in Bettona.
Day 2
TORGIANO, DERUTA, PERUGIA
From Museum Views To City Stroll
After breakfast, head to Torgiano to visit the Wine Museum, an engaging stop for both wine lovers and the simply curious. Nearby, you’ll have the chance to taste wines from Cantine Giorgio Lungarotti, one of Umbria’s most renowned producers. Spend the afternoon in Deruta, a town celebrated for its beautiful ceramics; we suggest visiting the National Museum of Pottery right in the village center. Later, stop in Perugia, an elegant city rich in monuments and famous for its chocolate—this is where the world‑famous Bacio candy was created. Enjoy dinner on your own and overnight.
Day 3
MONTEFALCO, ASSISI
A Day For Panoramas and Pilgrimage Atmosphere
After breakfast, travel to Montefalco, a gorgeous medieval town known as “the terrace of Umbria” for its sweeping views over the countryside. Visit an ancient olive oil mill, run by a local woman and her family, where you’ll taste traditional products and extra virgin olive oil accompanied by typical Italian snacks. The rest of the day is dedicated to Assisi at your leisure—explore the historic streets and, if you wish, visit the Basilica of St. Francis. Return to Bettona in the evening; dinner is on your own and overnight at the hotel.
Day 4
MONTEPULCIANO, PIENZA, SIENA
From Umbria’s Charm To Tuscany’s Famous Hills
After breakfast, check out and head into Tuscany. Your first stop is Montepulciano, a Renaissance hill town associated with the humanist poet Poliziano and notable works by great Italian architects. Enjoy a wine tasting with snacks and a tour in an ancient cellar in the historic center, then have lunch at leisure. In the afternoon, continue to Pienza, a charming town where you can get lost in its narrow, romantic streets, including the evocative Via dell’Amore. Arrive at your hotel in the Siena area (Siena or Monteriggioni), where you’ll have dinner on your own and spend the night.
Day 5
TUSCAN COOKING CLASS, SAN GIMIGNANO
From Countryside Kitchen To Walled Town Wandering
After breakfast, drive into the countryside to join a hands‑on cooking class in a traditional farmhouse. Learn some of the key secrets of Italian cuisine, such as making delicious fresh pasta, then enjoy a lunch based on the dishes you’ve created. In the afternoon, head to San Gimignano, a timeless medieval town famous for its skyline of towers and atmospheric streets. Spend time browsing local shops and soaking up the ambiance before returning to your hotel. Dinner is on your own and overnight in the Siena area.
Day 6
CHIANTI REGION, SIENA
Vineyard Morning, Medieval City Afternoon
After breakfast, set out for the Chianti region, a world‑famous wine area between Siena and Florence. Drive through rolling hills and vineyards, stopping in charming hamlets along the way. Visit a local winery for a tour of the estate and a tasting of Chianti wines. In the afternoon, return to Siena to explore at your own pace—stroll through its medieval streets, visit the Cathedral or simply relax in Piazza del Campo. Dinner is on your own and overnight in the Siena area.
Day 7
MONTALCINO
A Day That Ends Back With Wine Notes
After breakfast, travel to Montalcino, the hill town famous for its prestigious Brunello di Montalcino red wine. Visit a local estate for a winery tour and tasting, then enjoy lunch in a central trattoria. In the afternoon, we suggest visiting the intimate 11th‑century Romanesque church of Sant’Antimo, where you can appreciate the peaceful rhythm of monastic life. On the way back to the Siena area, stop at the impressive Benedictine Abbey of Monte Oliveto Maggiore, one of Tuscany’s most remarkable religious complexes. Return to your hotel for the night; dinner is on your own.
Day 8
MONTERIGGIONI or SIENA
From Rolling Hills To Real Life
After breakfast, check out of your hotel, marking the end of your Umbria and Tuscany food & wine journey. If time allows, we suggest continuing on to Florence or extending your vacation there for a few extra days to further explore the treasures of Tuscany.
