Panoramic view of the Val di Chiana, an alluvial valley of central Italy, in Tuscany

Summer in Southern Tuscany

July 6 - July 13, 2026

Experience the magic of Southern Tuscany like never before with our exclusive small-group tour, based in the charming hilltop town of Cortona, my new part time home town! Nestled between rolling vineyards and golden-hued valleys, Cortona, made famous by the book and movie Under the Tuscan Sun, offers the perfect blend of elegance, history, and authentic Italian charm. Your stay will be in a luxurious boutique hotel offering breathtaking views, personalized service, and the ultimate in comfort. Not to mention Italy’s best award-winning breakfast! Some amenities while at the hotel include mini-bar refill, complementary evening appetizers, and evening cantucci & Vin Santo. Also included is one complementary laundry service per room!

Each day is curated to awaken your senses—explore prestigious local wineries where you’ll sip world-class vintages right at the source. Join intimate cooking classes led by local chefs and learn the secrets behind perfect pasta, rich sauces, and traditional Tuscan desserts. Savor unforgettable meals at both rustic farmhouses and renowned restaurants, where each bite tells a story of passion and heritage.

This is more than a trip—it’s an immersive journey through the soul of Tuscany, all in the company of like-minded travelers who appreciate the finer things. With every detail thoughtfully arranged and every experience designed to inspire, this is your invitation to indulge, explore, and fall in love with the heart of Italy. Join me in my new home of Cortona, for an unforgettable escape you’ll treasure forever.

Day 1 - Let Your Tuscan Adventure Begin!

Benvenuti in Toscana!

Day one of your unforgettable culinary tour begins with your arrival and check-in at your luxurious boutique hotel, Hotel Villa Marsili, where comfort and elegance set the tone for the week ahead.

After settling into your beautifully appointed Superior room, you’re invited to the lounge for a warm welcome meet and greet with fellow food enthusiasts. Sip on refreshing cocktails and local wines as we discuss the week-long itinerary, filled with hands-on cooking classes, vineyard tastings, and exclusive dining experiences. Anticipation builds as you hear about the chefs you’ll meet and the regional delicacies you’ll savor.

As the sun sets, we will head to a charming local restaurant renowned for its authentic cuisine. The welcome dinner is a true feast—featuring seasonal ingredients, traditional techniques, and regional flavors—paired with perfectly matched wines. It’s the perfect beginning to a week of culinary discovery and gourmet indulgence.

Day 2 - Welcome to Cortona! Lunch with a Michelin-Starred Chef & Guided Visits to Lake Trasimeno & Cortona

Enjoy the award-winning breakfast at the hotel before departing for a full day of adventure!

We begin our day with a visit to nearby Lake Trasimeno. Touring Lake Trasimeno offers a captivating mix of natural beauty, history, and Italian charm. This tranquil lake is surrounded by picturesque towns like Castiglione del Lago and Passignano sul Trasimeno. Lake Trasimeno provides an authentic, less-crowded alternative to Italy’s more famous destinations, making it the perfect first stop for our tour.

After Lake Trasimeno, we return to Cortona for lunch. But not any lunch, today we will visit the Michelin-starred restaurant Relais Il Falconiere where starred chef Silvia Baracchi will prepare our delicious lunch with wine tasting.

After lunch, we will get to know our host city of Cortona with a guided tour. Touring Cortona is like stepping into a Tuscan dream. Perched on a hillside, this charming medieval town offers breathtaking views of the Val di Chiana and Lake Trasimeno. We will wander narrow cobblestone streets lined with Renaissance architecture, artisan shops, and quaint cafés. You’ll soon see why I bought a home here!

Day 3 - Truffle Hunt in the Woods with Cooking Class Following & Visit to Pienza

Today, we immerse ourselves in the enchanting world of truffles with a unique experience at one of our favorite farms. Upon arrival, we will  be welcomed by Sandra, the farmhouse owner, and begin the first part of our cooking class by preparing fresh pasta dough. While the dough rests, we will receive an introduction to truffles and their fascinating role in Italian cuisine, all within the warm setting of our farm restaurant. Next, we will venture into the surrounding woods with our expert truffle hunter and his specially trained dog, searching for these culinary treasures in their natural habitat. After the hunt, you’ll return to the farmhouse for the second part of the cooking session, where we will craft a full truffle-based menu—first course, main dish, and even dessert—using organic ingredients from the farm. Throughout the class, Sandra shares stories of her life on the farm and insights from over twenty years of sustainable farming. The experience culminates in a delicious four-course meal, including homemade starters, a cheese platter from the owner’s farm, and the truffle dishes we’ve created, accompanied by wine, water, coffee, and fresh-baked bread.

After our experience on the farm, we will walk off our lunch with a visit the enchanting town of Pienza. Nestled in Tuscany’s Val d’Orcia, area, Pienza is a pure gem known for its harmonious architecture, charming streets, and stunning countryside views, its famed for pecorino cheese and romantic ambiance. A UNESCO World Heritage Site, Pienza blends history, art, and pastoral beauty in perfect harmony.

Day 4: Pecorino Cheese Tasting, Picnic in the Fields & Visit to Montepulciano

Today we visit local farm and learn all there is to know about true and authentic Tuscan pecorino cheese. Tasting pecorino cheese is a bold, savory experience. This sheep’s milk cheese delivers a firm texture with a slightly oily feel. The flavor is salty, nutty, and sharp, intensifying with age. Younger pecorino offers a milder, creamier bite, while aged varieties like pecorino Toscano boast a crumbly texture and a pungent, lingering tang. On the tongue, it starts salty, then reveals earthy, grassy undertones. We will taste several varieties, paired with wines, honey, fruit spreads.

After our cheese tasting experience, we will head out into the fields to enjoy an amazing picnic style lunch enjoying more cheeses and salumi, all paired with more local wines! After lunch we will visit another Tuscan gem: Montepulciano!

Visiting Montepulciano is like stepping into a Renaissance painting. This charming Tuscan hill town offers breathtaking views, winding cobblestone streets, and beautifully preserved medieval architecture. The Piazza Grande, the heart of the town, hosts festivals and is perfect for walking off lunch. Montepulciano will capture your soul with its beauty, culture, and timeless Italian charm.

Day 5 - Hands-On Cooking Class & Guided Tour of Arezzo

Today, we visit the Etruscan town of Arezzo. Touring Arezzo offers a captivating journey through history, art, and Tuscan charm. This medieval city, nestled in the rolling hills of eastern Tuscany, boasts Roman ruins, Gothic churches, and Renaissance treasures. Art lovers can admire frescoes by Piero della Francesca in the Basilica of San Francesco. Antique markets, boutique shops, and rustic trattorias fill the cobbled streets. Arezzo is less crowded than other Tuscan cities, allowing for a more relaxed, authentic experience. It’s a perfect blend of cultural richness and timeless Italian beauty!

But before we visit Arezzo, we will return in the kitchen for another hands-on cooking class in a refurbished abbey. As the process of renovation began in 2017, one thing became clear to the owners: the beauty and uniqueness of the abbey rested firmly on two cornerstones – its centuries-long history and its deep connection to the environment. So much, yet, so little has changed with regards to the abbey’s beauty. But our cooking class is not just about delicious food or a charming setting—it’s about the heart of Italian culture. Our recipes have been passed down through generations, evolving over time yet always staying true to their roots. If you’ve ever dreamed of unlocking the secrets of Tuscan traditions, there’s no better way than by joining our passionate chefs in a hands-on cooking class. We will learn to craft a variety of traditional pasta dishes and sauces, all made with the freshest local ingredients. Then, sit down and savor our creations with a glass of fine wine—a perfect ending to our culinary journey.

Day 6 - Extra Virgin Olive Oil Tasting & Lunch, & Afternoon Visit to Siena

This morning is all about extra virgin olive oil! We will visit a local oil (and wine) producer that produces some of the area’s best EVOO. Crafted exclusively from 100% Tuscan olives—Moraiolo, Leccino, and Frantoio varieties, the olive trees are cultivated across various parts of the Cortona area, following traditional, non-intensive farming methods. The olives are carefully hand-harvested at the end of October. Production is limited and naturally varies with the season and climate. The oil is cold-pressed to retain its full range of organoleptic qualities.

After our lunch, we will visit the amazing town of Siena. This Tuscan gem captivates with its winding cobblestone streets, stunning Gothic architecture, and the iconic Piazza del Campo. The Duomo di Siena dazzles with intricate marble work and historic art. Time seems to slow down here, inviting you to savor every moment. Siena’s warm, timeless charm leaves a lasting impression on every traveler.

Day 7: A Day at the Farm & Farewell Dinner

Today, we embark on an unforgettable journey into the heart of rural life with a farm experience that’s perfect for gourmands seeking authentic connection with nature, tradition, and each other. Stroll through lush fields, sun-kissed vineyards, ancient olive groves, buzzing beehives, and colorful orchards, where every step offers something new to discover. The guided tour takes us up close to friendly farm animals and introduces you to time-honored, sustainable farming practices. Watch the magic behind artisanal cheese-making unfold, and learn the stories and skills passed down through generations. The experience culminates in a delightful tasting session, where we will savor the farm’s freshest products—cheeses, olive oil, honey, and more.

Finally, relax and indulge in a delicious, organic farm-to-table lunch at a charming countryside taverna, surrounded by the peaceful sounds and sights of nature. It’s not just a tour—it’s a sensory adventure that nourishes body, mind, and soul.

In the evening, we will have a light dinner at “Casa Luce” – Francesca’s personal home for an evening of fun and cheer before ending our time together in Tuscany!

Day 8 - Breakfast at the Hotel Before Checking-Out

After breakfast at the hotel, we say our good-byes and reflect on the beautiful week we just experienced.

 

NOTE: As we partner with small, family-run businesses, some flexibility in the above itinerary is necessary. We may adjust the schedule, modify activities, or substitute locations to ensure the best possible experience. A finalized itinerary will be provided two weeks before our adventure begins.

Price & Details

8 Days / 7 Nights

$5,750 USD Per Person for Double Occupancy Superior Room / Single Supplement $850.00.

$1,000 USD Non-refundable deposit is required to secure your spot.

Francesca Montillo, Native Italian, Owner and Tour Leader Accompanies all Activities​​. Contact Francesca at francesca@thelazyitalian.com for booking/reservation and further details.

If you would like to reserve a spot for this tour, or have any questions, please use the contact form below and we will send you the necessary booking instructions or additional information.

Included

  • 8 days / 7 night in beautiful hotel with award-winning breakfast, stunning views, amazing rooms, private bathrooms.
  • Welcome multi-course dinner in Cortona.
  • Two hands-on cooking classes with large meals following.
  • Guided tour of Lake Trasimeno & Cortona.
  • Lunch and wine tasting with Michelin-Star Chef in Cortona.
  • Truffle hunting in the woods with hands-on truffle themed cooking class afterwards.
  • Unguided shopping and sightseeing time in Pienza.
  • Pecorino cheese-tasting with picnic following.
  • Unguided shopping and sightseeing time in Montepulciano.
  • Visit to a pecorino cheese farm, and enjoy a cheese-themed lunch afterwards.
  • Guided tour in Arezzo with time on your own to explore.
  • Olive oil tasting lesson and lunch on a farm.
  • Guided time in Siena with time on your own to explore.
  • A full day on a farm with education on farming, local products and large lunch following.
  • Apericena at "Casa Luce" - Francesca's private home.

Not Included

  • Airfare / Flights (Participants should fly into Florence or Rome International Airport).
  • Transfer from / to airport to Cortona upon arrival and departure.
  • Tips / gratuities for guides, instructors and drivers 
  • Travel Insurance-Click Here for Options

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