8 days, 7 nights · Best for Wine lovers and hill town explorers seeking quiet Umbria and rural Tuscany
Small gems of Umbria and Tuscany Tour
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.
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Bettona, Umbria
Bettona
Green hills and artisan towns of central Umbria
Bettona is a medieval hilltop village wrapped in Etruscan walls, smaller and quieter than Assisi twenty minutes north. The green Umbrian plain spreads below. Your three nights here anchor day trips to Torgiano's wine museum and the Lungarotti cellars, Deruta's pottery workshops and museum, and Perugia's chocolate shops and monuments. Montefalco, the terrace of Umbria, offers sweeping views and a family-run olive mill where you taste oil with bread and local snacks.
Assisi is yours at leisure for an afternoon. Walk the stone lanes, visit the Basilica of St. Francis if you wish, then return to Bettona for the evening. The rhythm is unhurried, the scale intimate, the food deeply Umbrian.
Arranged for you: We arrange three nights in Bettona, a welcome dinner, wine tasting at Cantine Giorgio Lungarotti, and an olive oil tasting with snacks at a family mill in Montefalco.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Bettona
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Private truffle hunt with a local hunter and his dog Day Trips · Half day
Walk the oak woods in search of tuber, then taste your find shaved over warm eggs at the farm.
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Ceramics workshop in Deruta with a master potter Day Trips · Half day
Learn hand-painting techniques on bisque tiles and take home your own signed piece.
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Private after-hours visit to Perugina chocolate factory Day Trips · Half day
Tour the production line, see how Baci are wrapped, and taste samples straight from the line.
Day by day in Bettona
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.
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.
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.
Stop 2Siena or Monteriggioni, Tuscany
Siena Area
Towers, vineyards and Tuscan cooking in the countryside
Your four nights are based in the countryside near Siena or in the walled hamlet of Monteriggioni, a ring of stone towers on a hill between Siena and San Gimignano. From here you reach Montepulciano for a cellar tasting and Renaissance architecture, and Pienza for the Via dell'Amore and pecorino cheese. A hands-on cooking class in a farmhouse teaches you fresh pasta shapes, then you eat what you made. San Gimignano's medieval towers and stone streets are yours for an afternoon of browsing and gelato.
The Chianti region fills a full day of vineyard driving and winery visits. Siena itself is at leisure, walk the Campo, climb the Torre del Mangia if the line is short, or sit with an espresso and watch the passeggiata. Montalcino brings Brunello tastings at a local estate, lunch in a trattoria, and a visit to Sant'Antimo abbey or Monte Oliveto Maggiore on the return.
Arranged for you: We arrange four nights in the Siena area, a wine tasting with snacks and cellar tour in Montepulciano, a hands-on cooking class with lunch, a Chianti winery visit with tasting, and a Montalcino estate tour with Brunello tasting and lunch.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Siena Area
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Private truffle tasting menu at a Michelin-starred Tuscan restaurant Day Trips · Half day
Six courses pair white and black truffle with house-made pasta, risotto and local wines.
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Hot air balloon flight over the Chianti vineyards at sunrise Day Trips · Half day
Lift off from a hilltop estate, drift over terraced vines and olive groves, then land for prosecco and pastries.
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Private vespa tour of the Crete Senesi clay hills Day Trips · Full day
Ride vintage scooters along white roads past wheat fields and cypress alleys, stopping at a farmhouse for lunch.
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Pecorino cheese tasting with a shepherd in the Val d'Orcia Day Trips · Half day
Visit the flock, walk through the aging cellar, then taste three pecorinos with honey and preserves.
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Cooking Class with Dinner in Siena Food and Wine · Tour in a DayCook Siena-style in the heart of the old town. Hands-on Tuscan classics, local chefs, and recipes you’ll actually remake at home.
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Private Tour Excursion to Siena & San Gimignano Guided Tours and Sightseeing · Tour in a DayDiscover Tuscany’s legendary charm in style, explore Siena and San Gimignano with the luxury of your own private driver.
Day by day in Siena Area
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.
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.
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.
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
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.
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
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They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
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Questions travelers ask
How do we get between the destinations?
Transportation is arranged as part of the itinerary, with vehicle and train transfers as the itinerary requires. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
Is this package a good fit for our group?
It suits travelers who want Italy arranged by experts, with guided experiences balanced by free time to explore on your own.
Is this package customizable?
It is. This itinerary is a sample built to spark ideas, and every element can be customized to your wishes and needs by your travel consultant. A minimum of 2 travelers applies.
When should we travel on this package?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.