ITALY HARVEST TOUR

SEPTEMBER 2026

September 14-23, 2026

$6775 Double / $7375 Single per person

Prepare to be enchanted by picturesque landscapes, rich culture, and unforgettable moments in the true heart of Italy. Beyond the bustling crowds of typical tourist spots, discover the authentic charm of Umbria, Tuscany, and Le Marche. These captivating regions offer a symphony of experiences: wander through ancient hill towns brimming with art and history, from breathtaking Gothic cathedrals to Renaissance masterpieces. Indulge in unparalleled culinary adventures, savoring world-renowned wines, hunting for precious truffles, learning to craft regional delicacies, and feasting on farm-to-table delights. But it’s not just about beauty and food – get ready for a lot of fun! Experience vibrant local traditions, immerse yourself in traditional productions and grape harvests, and embrace the joyful spirit of Italy.

Day One

Overnight: Orvieto

Benvenuto 

Arrive in Orvieto and settle into your hotel. The afternoon is yours to wander through its ancient streets and soak in the atmosphere. With a local guide, you will have a first orientation walk to unveil the secrets of this Etruscan town. Welcome dinner in a typical local restaurant.

Day Two

Overnight: Orvieto

Cathedral and Wine

Following a delicious breakfast, meet your guide in Orvieto to explore the breathtaking cathedral, a masterpiece of Gothic architecture. Afterwards, journey to a charming wine estate nestled in the rolling hills surrounding Orvieto. Here, you’ll savor a delightful lunch of local culinary treasures paired with regional wines. In the afternoon, embark on an excursion to the breathtaking Civita di Bagnoregio, the “dying city,” perched dramatically atop a tufa hill. Explore its unique charm and history before returning to Orvieto.

Day Three

Overnight: Ascoli Piceno

Truffle Hunting

After a hearty breakfast, venture into the stunning Valnerina region. Arrive at a charming hamlet for an exhilarating truffle hunting adventure on a private estate. You’ll be warmly welcomed to a secluded house nestled in the mountains. Following the exciting hunt, enjoy a leisurely walk through the olive groves, where you’ll learn about the production of Umbria’s prized extra-virgin olive oil, from the late October harvest to the pressing process. Participate in a hands-on cooking class and savor a delectable lunch featuring the prized black truffle. In the afternoon, transfer to Le Marche region, Ascoli Piceno.

Day Four

Overnight: Ascoli Piceno

Tastings and Cooking

Journey to Campofilone, a town celebrated for its exceptional Italian pasta. Here, you’ll visit a traditional workshop and uncover the fascinating story behind this beloved staple. Enjoy a delicious lunch featuring “Maccheroncini di campofilone” with ragout Sauce, and tomato sauce, and a glass of local wine (Passerina) – water is also included with pasta dishes. In the afternoon, embark on a fantastic cooking class in Ascoli. You will learn how to prepare and cook Ascolane Olives. This is a regional but internationally famous delicacy of Ascoli. Olives stuffed with meat and fried. At the end of the class, a glorious tasting with a local glass of wine.

Day Five

Overnight: Sagrantino 

Caseficio Day

Departure to the Sibillini mountains, the highest peaks of the Apennines, between Umbria and Marche. It will feel like stepping into a painted landscape, with the breathtaking tapestry of emerald and gold stretching towards the horizon. You will observe flocks of sheep scattered across the plain, and a shepherd will share local legends and traditions with you. Next, visit a local caseificio, or cheese factory. You will learn about the different production stages, from fresh ricotta to the aged pecorino, undoubtedly influenced by the milk of those very sheep. Finally, a lunch with panoramic views of Piangrande. Lunch will be a feast of local specialties including the exquisite pecorino cheese, accompanied by crusty bread, and local wine. In the afternoon, transfer to the heart of Umbria for accommodations in a charming agriturismo.

Day Six

Overnight: Sagrantino

Grape Harvest

Experience the age-old tradition of the grape harvest firsthand at the farm, followed by a delightful picnic amidst the picturesque vines, savoring the fruits of the land.

Day Seven

Overnight: Sagrantino

St Francis of Assisi

Transfer to the spiritual center of Assisi, where a local English-speaking guide will lead you through the magnificent Basilica of Saint Francis, a testament to faith and art. Visit to a friars’ community in Assisi and tasting of their wines and liquors.

Day Eight

Overnight: Pienza

Perugia and Tuscany

Leaving the idyllic Umbria behind, you’ll journey to Tuscany, but your first stop is Perugia, the vibrant capital city of Umbria, where you’ll discover a vibrant glass factory run by talented women. As part of our guided visit to Perugia, we’ll also delve into a beloved local tradition: chocolate. We’ll have a dedicated stop where you can enjoy a tasting of this city’s sweet specialty. Finally, transfer to Pienza, in the heart of Orcia Valley. It’s a testament to the vision of Pope Pius II, who transformed his humble birthplace into an ideal city, perched on a Tuscan hilltop, with its breathtaking panoramic views of the rolling Val d’Orcia.

Day Nine

Overnight: Pienza

Siena and Montalcino

Today, you’ll travel to the elegant town of Siena. Explore the architectural beauty and cultural heritage of Siena with a local expert guide. At the end of the walking tour, a special welcome in a fantastic location, a palace in Piazza del Campo, where you will taste local cakes (cantucci, panforte, saporelli, and more) with sweet wine and the story of these traditions. In the afternoon, you’ll head to the picturesque Montalcino, where you’ll tour a traditional farm producing fine wines, fragrant olive oils, and rich vinegars. On a sun-drenched terrace overlooking the rolling vineyards of Montalcino, our glorious tour of Italian food and traditions culminates in a wine tasting. This final tasting is a perfect, flavorful farewell to this Italian adventure, a lasting memory of the country’s rich culinary heritage.

Day Ten

Tour Ends

Our Italy harvest tour ends after breakfast. Your guide will be on hand to help with transfers to the airport or wherever your adventures take you. Grazie and arrivederci!

MEET YOUR GUIDE: Lisa Anderson
Lisa Anderson is a professional tour guide in Italy, working for Rick Steves since 1999 and Adventures with Sarah since 2021. She moved to Italy temporarily to teach English in the 90’s and fell in love with the country…and an Italian man. Lisa spends her time guiding tours, exploring the region and cooking up a storm with her garden’s produce. She lives in Piedmont with her husband and sons.
ADDITIONAL INFORMATION

Price: $6775 (Air not included) per person for a double room. Single Supplement is $600. We welcome singles and if you do not have a travel partner, please sign up for a single spot. In the event that a roommate is found, your booking can be changed to a double before final payment is due.

What’s included: all breakfasts, 5 lunches, 2 dinners, tastings, and 9 nights lodging in a clean, comfortable, and centrally located hotel. All transportation during the tour, tips, included activity fees, and private guides.

You can reserve a spot on this tour with a nonrefundable deposit of $600.

Tour begins in Orvieto and ends in Pienza (closest international airport is Perugia (PEG)). 

Email info@adventureswithsarah.net with any questions.

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