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Overview

Southern Tuscany Retreat: Under the Tuscan Spell
53047 Sarteano, Province of Siena, Italy
May 23 - 30, 2026
Together in Tuscany image
Together in Tuscany
$3,800
Deposit: $500

About your trip

Feel your senses come alive while falling in love with the Tuscan region of the Val d’Orcia.

Beyond the well-trodden path of Northern Tuscany lies the Val d’Orcia, where vineyards are replaced with wheat fields (think scenes from the Gladiator movie and the Netflix Medici series). Each day is filled with a sensory discovery: wandering through nearby Pienza and Montepulciano, tasting delicious wine, and meeting the owner of an olive grove while sampling their olive oil along with a home-cooked meal. This is the Tuscany most travelers never find, but we’ll take you there.

Your home for the week is a luxurious villa in the tranquil town of Sarteano, rich in Etruscan history. This villa has all the charm of a 1700s home with all the modern amenities due to the careful restoration by its current owners. Here you’ll be pampered by chef-prepared meals, the ease of walking into Sarteano, expansive areas to gather with other guests, and an in-villa cooking class. You’ll experience the perfect blend of relaxation, exploration, and connection.

Saturday

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Welcome to Tuscany!

4:00 Villa Check-In

You will be picked up from the Chianciano train station and driven to the beautiful villa, where you will feel the warm welcome of your surroundings. Upon arrival, you will have the delightful opportunity to meet the others in your group, creating an atmosphere of camaraderie and excitement. As you settle in, enjoy a selection of the region’s finest wine and artisanal cheese during a charming welcome reception at the villa, allowing you to savor local flavors. Following this, immerse yourself in a guided tour of the villa, where you can appreciate its stunning architecture and history, before concluding your evening with a delicious dinner served within the villa’s inviting ambiance.

Sunday

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Montepulciano

Step back in time as you wander through the enchanting Renaissance town of Montepulciano, where every cobblestone street tells a story. Explore its charming architecture and soak in the rich history that surrounds you. As you meander, indulge in the exquisite flavors of the renowned Nobile di Montepulciano wine in one of the fascinating historical wine cellars. Here, you’ll have the opportunity to learn about the winemaking process that has been perfected over centuries. To complement your tasting experience, you will enjoy a delicious traditional Italian lunch, savoring each bite while sipping on your wine, creating unforgettable memories in this picturesque setting.

Monday

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Olive Oil Tasting

Visit a picturesque family-owned olive grove in Cetona, where you'll have the unique opportunity to learn about the traditional olive oil-making process. Enjoy a delicious homemade lunch, thoughtfully crafted with fresh, local ingredients, paired perfectly with exquisite olive oil selections that enhance each dish’s flavors. This experience promises to be a delightful blend of culinary pleasure and cultural immersion, making for a memorable day.

Tuesday

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Pienza

Explore the ancient village of Pienza, known for its pecorino cheese.

Wednesday

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Cooking Class

Learn to make classic Italian dishes in a hands-on cooking class alongside a skilled Italian chef. This immersive experience will allow you to prepare a delicious 4-course meal in the beautiful setting of the villa, where you’ll discover the secrets behind traditional recipes and cooking techniques. Enjoy the rich flavors of Italy as you chop, sauté, and bake your way to a culinary triumph, all while gaining insights into the culture and history of Italian cuisine. By the end of the class, you’ll not only have created a mouthwatering meal but also lasting memories and new skills to impress your friends and family back home.

Thursday

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Pienza

Visit and enjoy a delightful lunch at a charming, family-run organic farm that specializes in the rich flavors of goat and sheep cheese. Here, you will have the opportunity to taste a variety of artisanal cheeses crafted with care and passion. Afterward, take a leisurely stroll through the picturesque town of Pienza, where you can uncover hidden treasures such as a contemporary sculptor's gallery and a talented ceramics artisan's workshop. Engage with local artists and immerse yourself in the vibrant culture that makes this area so special.

Friday

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Explore the Weekly Market in Sarteano

Walk to the charming outdoor weekly market in Sarteano, where you can explore local produce, handmade crafts, and enjoy the vibrant atmosphere filled with friendly vendors

Saturday

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Arrivederci

As we come to the end of our wonderful journey together, we say goodbye until next time, cherishing the memories we've created. We hope to see you again soon for more adventures and experiences.

Please remember to check out by 10:00 am to ensure a smooth departure. A taxi will take you the Chianciano train station. Thank you for being a part of this amazing trip!

Location

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1. 53047 Sarteano, Province of Siena, Italy

53047 Sarteano, Province of Siena, Italy

About your organizer

Ciao, I’m Janine, certified professional coach for mid-life women and founder of Together in Tuscany. I create intimate, villa-based journeys designed to help women reconnect with themselves through transformational travel. Our small groups (8–14 guests) allow for genuine connection with each other and the immersive experiences that we thoughtfully curate. We seek out ancient traditions and local artisans so we can learn more deeply about the places we visit. This isn’t just another trip. It’s a beautiful pause made just for you.

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© 2026 Together in Tuscany