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Overview

Women's Small-Group Retreat: A Taste of Chianti, Tuscany
50026 San Casciano In Val di Pesa, Metropolitan City of Florence, Italy
May 30 - Jun 6, 2026
Together in Tuscany image
Together in Tuscany
$2,000
Deposit: $500

About your trip

Imagine waking up in a sun-drenched villa overlooking rolling Tuscan hills with the sounds of nature floating through the air. You catch the scent of breakfast cooking and fresh espresso, while laughter drifts across the dining room. This is more than a vacation. It’s an invitation to slow down, savor life, and experience Tuscany with all your senses.

This 8-day, 7-night Chianti Tuscany villa retreat invites you to leave your to-do lists behind and fully immerse yourself in the beauty, flavors, and rhythms of Italian life. Designed to nourish your mind, body, and soul, this experience blends relaxation, cultural discovery, and meaningful connection.

Your home for the week is a historic 400-year-old villa in the Chianti region of Tuscany, located on a working vineyard and within walking distance of the charming village of San Casciano in Val di Pesa, just 24 minutes from Florence. Surrounded by rolling vineyards and olive groves, the villa offers panoramic countryside views and estate-produced Chianti wines served right where they are grown.

During your stay, you’ll enjoy chef-prepared Tuscan meals, time to wander into town for coffee or shopping, and expansive spaces to gather with fellow guests.

Saturday

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Welcome to Tuscany!

4:00 Villa check-in

Welcome reception with wine and apperitivi


Sunday

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Winery Tour and Tasting With Lunch

Monday

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San Casciano Market and Cheese Tasting

Explore the outdoor market in San Casciano. Visit a family-run sheep farm to learn how they make Pecorino cheese. Enjoy tasting their cheese, wine, and olive oil.

Tuesday

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Explore San Gimignano

Wednesday

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Enjoy the Villa and Nearby San Casciano

Thursday

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Olive Oil Mill Tour and Tasting Experience

Friday

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Cooking Class

Learn to make classic Italian dishes in a hands-on cooking class alongside an Italian chef. You will prepare a delicious 4-course meal in a historic kitchen paired with the estate’s incredible wine.

Saturday

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Arrivederci

We say goodbye until next time.

Check out by 10:00 am

Location

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1. 50026 San Casciano In Val di Pesa, Metropolitan City of Florence, Italy

50026 San Casciano In Val di Pesa, Metropolitan City of Florence, 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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