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A Taste of Chianti, Tuscany

October 10-17, 2026
A Taste of Chianti, Tuscany image

For women craving connection, culture, and self-discovery through exceptional wine, food, and slow Italian living.

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About this trip

Imagine waking up in a sun-drenched villa overlooking rolling Tuscan hills with the sounds of nature floating through the air.

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.

Tuscan Retreat Highlights

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At a glance

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About this trip

Day 1 - Welcome to Tuscany and Villa Arrival

Saturday, October 10, 2026
Day 1 - Welcome to Tuscany and Villa Arrival image

Arrive in Tuscany, Villa Check-in and Welcome Reception

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Welcome to Tuscany!

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.

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Villa in Chianti, Tuscany

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

Villa check-in is at 4:00 PM. Upon arrival, you will be greeted by the villa staff. Take a moment to unwind and soak in the serene surroundings, where rolling vineyards and picturesque landscapes create a perfect setting for relaxation.

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Day 2 - Winery tour with tasting and lunch

Sunday, October 11, 2026
Day 2 - Winery tour with tasting and lunch image
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Winery tour with tasting and lunch

Experience the beauty of the Chianti region with a delightful visit to a renowned winery. Your day begins with a guided tour through the picturesque vineyards, where you’ll learn about the winemaking process and the unique terroir that makes Chianti wines so special. After the tour, indulge in a tasting session featuring a selection of exquisite wines, paired with local cheeses and charcuterie. To top off your experience, enjoy a sumptuous lunch prepared with fresh, seasonal ingredients, allowing you to savor the flavors of Tuscany while taking in the stunning views of the rolling hills.

Day 3 - San Casciano Market and Cheese Tasting

Monday, October 12, 2026
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Explore San Casciano Market and Cheese Tasting

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San Casciano Market and Cheese Tasting

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.

Day 4 - Explore Siena

Tuesday, October 13, 2026
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Discover Siena's Medieval Charm

Siena captivates visitors with its beautiful medieval architecture and rich cultural heritage. The city's vibrant festivals, especially the thrilling Palio horse race, make it a unique destination. Explore the stunning Piazza del Campo and admire the Gothic facade of the Siena Cathedral for an unforgettable experience.

Day 5 - Enjoy the Villa and Nearby San Casciano

Wednesday, October 14, 2026
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Relax at the Villa and Explore San Casciano

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Enjoy the Villa and Nearby San Casciano

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.

Day 6 - Winery tour with tasting and lunch

Thursday, October 15, 2026
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Winery Tour with Tasting and Lunch

Visit a nearby 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.

Day 7 - Cooking Class

Friday, October 16, 2026
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Cooking Class

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.

Day 8 - Departure

Saturday, October 17, 2026
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Activity

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!

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1. Florence

Florence, Metropolitan City of Florence, Italy

2. Villa in Chianti, Tuscany

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

3. Siena

53100 Siena, Province of Siena, Italy

What's included/not included

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Inclusions

  • 7 nights/8 days accommodations in an ancient villa

  • Stocked refrigerator for self-catered breakfasts

  • 5 chef-prepared meals at the villa

  • Transfers to and from Florence train station

  • 2 winery tours and tastings with lunch

  • 1 cheese farm tour with tasting and lunch

  • 1 cooking class with wine tasting

  • 1 day trip to Siena

  • Transportation to activities

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Exclusions

  • Airfare

  • Meals or alcohol not mentioned in the itinerary

  • Travel Insurance

  • Personal expenses

  • Gratuities

  • Transfers to the airport instead of the train station may incur an extra charge

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Trip Cost - $3,500 per person

Contact Us

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Get in Touch with Us

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

About your organizer

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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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Travel Tips Italy

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Travel Tips

  1. Pack light, preferably with carry-on luggage.

  2. 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.

  3. Learn a few basic phrases in Italian to enhance your experience - locals appreciate the effort!

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A Few Useful Italian Phrases

Here are some basic phrases that can be helpful when traveling to Italy:

  1. Ciao (chow) - Hi / Bye (informal).

  2. Grazie (GRAHT-see-eh) - Thank you.

  3. Per favore (pehr fah-VOH-reh) - Please.

  4. Prego (PREH-goh) - You're welcome / Please (when offering something).

  5. Mi scusi (mee SKOO-zee) - Excuse me / Pardon me (formal/general).

  6. Buongiorno (bwon-JOR-no) - Good morning/day.

  7. Buonasera (bwoh-nah-SEH-rah) - Good evening.

  8. Dov'è il bagno? (doh-VEH eel BAH-nyoh?) - Where is the bathroom?.

  9. Quanto costa? (KWAN-toh KOS-tah?) - How much does it cost?.

  10. Non parlo italiano (non PAR-loh ee-tal-YAH-noh) - I don't speak Italian.