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.
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.
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.
Villa check-in is at 4:00 PM. Upon arrival, you will be greeted and escorted to your stunning villa, which offers breathtaking views of the enchanting Tuscan hills. Take a moment to unwind and soak in the serene surroundings, where rolling vineyards and picturesque landscapes create a perfect setting for relaxation.
Once you're settled, join us for a delightful welcome reception where you can unwind and socialize with fellow travelers. Enjoy a selection of exquisite wines paired with delicious apperitivi that will tantalize your taste buds. This is the perfect opportunity to relax, mingle, and kick off your adventure in style!
After the delightful lunch experience, take some time to wander through the charming, ancient village of Greve. As you stroll along the cobblestone streets, immerse yourself in the rich history and culture that surrounds you. Explore the unique artisan shops that line the village, each offering a variety of handcrafted goods. Don’t miss the chance to choose a leather belt that is custom cut right before your eyes, allowing you to witness the skilled craftsmanship that goes into creating such a beautiful piece.
Explore the vibrant outdoor market in San Casciano, where you can immerse yourself in the local culture and discover a variety of fresh produce, clothing, shoes and housewares.
Afterward, visit a charming family-run sheep farm nestled in the picturesque countryside. Here, you will learn the fascinating process of how they make their renowned Pecorino cheese, using traditional methods passed down through generations.
To top off your experience, enjoy a delightful tasting session featuring their delicious cheese, paired with exquisite local wine and rich olive oil, allowing your taste buds to savor the authentic flavors of this beautiful region.
Enjoy a scenic drive through the picturesque landscapes to Radda in Chianti, where you will embark on a luxurious winery tour at Colle Bereto, and indulge in a delightful wine tasting experience that showcases the region's finest offerings.
Alternatively, spend a memorable day exploring the charming parts of the Chianti area on a guided e-bike tour. This exciting adventure includes stops at three quaint small villages, a delightful wine shop, and culminates at a beautiful winery where you will enjoy a delicious lunch, perfectly paired with local wines.
The e-bike tour is an optional add-on to the itinerary, providing you with the flexibility to choose your preferred experience.
Enjoy the serenity of the villa and its beautiful surroundings with a leisurely day spent on the property. You can take a relaxing stroll into the charming village of San Casciano, where you can indulge in a delightful lunch at a local café and explore unique shops filled with local crafts and specialties.
An alternative option is to visit the nearby Casa Emma winery, where you can enjoy an engaging tour of the vineyard, participate in a tasting of their exquisite wines, and savor a delicious lunch paired perfectly with their selections. This experience truly immerses you in the rich flavors of the region.
Enjoy a guided tour of the enchanting city of Siena, where you will uncover its rich history and stunning architecture. With knowledgeable guides leading the way, you’ll visit iconic landmarks and hear fascinating stories.
After the tour, you'll have ample time to explore this beautiful city on your own, allowing you to wander through its charming streets, shop for souvenirs, and soak in the local atmosphere.
Don't miss the opportunity to enjoy a delicious lunch at one of the many delightful restaurants or cafes in town, sampling authentic Tuscan cuisine while surrounded by the picturesque scenery.
Rediscover the scents and flavors of the Tuscan culinary tradition in a cooking class held in the 17th-century kitchen of Villa Le Corti. Experience aromas and recipes of the past, using local ingredients, fresh herbs from the garden—hand-picked by you—and techniques handed down over the centuries.
The historic kitchen sets the stage for an unforgettable experience.
Your day begins with a visit to the historic wine cellar and the vegetable garden before getting your hands messy. During the lesson, you will taste the dishes you prepare, accompanied by a sampling of Principe Corsini wines and olive oil.
As we come to the end of our delightful 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 and allow for any final arrangements. A driver will transport you from the villa to either the Florence train station or airport. Thank you for being with us!
Accommodations
Meals and Activities as outlined in the itinerary
Airport Transfers
Local Transfers
Gratuities
Wine with dinner
Use the Book Now button to secure your booking with a $500 deposit. The balance payment is due 120 days prior to your trip departure.
Flights
Meals or Alcohol not mentioned in the itinerary
Travel Insurance
Personal expenses
We're here to help you plan the perfect journey! For any inquiries or assistance, feel free to reach out:
Phone or WhatsApp: +1 703 473 5624
Email: info@together-in-tuscany.com
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.
Travel Tips
Pack light, preferably with carry-on luggage.
Plan to use an ATM when you arrive so you can have Euros on hand for personal purchases where credit cards may not be accepted.
Learn a few basic phrases in Italian to enhance your experience - locals appreciate the effort!
Here are some basic phrases that can be helpful when traveling to Italy:
Ciao (chow) - Hi / Bye (informal).
Grazie (GRAHT-see-eh) - Thank you.
Per favore (pehr fah-VOH-reh) - Please.
Prego (PREH-goh) - You're welcome / Please (when offering something).
Mi scusi (mee SKOO-zee) - Excuse me / Pardon me (formal/general).
Buongiorno (bwon-JOR-no) - Good morning/day.
Buonasera (bwoh-nah-SEH-rah) - Good evening.
Dov'è il bagno? (doh-VEH eel BAH-nyoh?) - Where is the bathroom?.
Quanto costa? (KWAN-toh KOS-tah?) - How much does it cost?.
Non parlo italiano (non PAR-loh ee-tal-YAH-noh) - I don't speak Italian.