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Women's Small-Group Retreat: A Taste of Tuscany

May 30 - June 6, 2026
Women's Small-Group Retreat: A Taste of Tuscany image

For women craving connection, culture, and self-discovery through the flavors of Tuscany 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. You catch the scent of 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 for quiet moments or 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, May 30, 2026
Day 1 - Welcome to Tuscany and Villa Arrival image

Arrive in Tuscany, Villa Check-in and Welcome Reception

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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 with a tout of your stunning villa, which offers breathtaking views of the enchanting Tuscan hills. Take a moment to unpack and soak in the serene surroundings, where rolling vineyards and picturesque landscapes create a perfect setting for your retreat.

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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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Welcome reception with wine and apperitivi

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!

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Dinner at the Villa Le Corti Osteria

A short walk at the end of the villa driveway.
Time7:00 p.m.

Day 2 - Winery Tour with Lunch

Sunday, May 31, 2026
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Winery Tour and Lunch at Casa Emma

Experience the charm of Azienda Agricola Casa Emma, where stunning views of the Chianti landscape meet traditional Tuscan cuisine crafted from local ingredients. Enjoy an extensive selection of house-made wines, alongside unique wine tasting events and vineyard tours. This family-run establishment offers a warm atmosphere, making every visit memorable.
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Day 3 - San Casciano Market and Cheese Tasting

Monday, June 1, 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.

Explore Fattoria Corzano and Paterno, where scenic Tuscan landscapes meet high-quality wines and cheeses. Delight in guided tours that reveal traditional farming practices while enjoying artisan products crafted from local ingredients. Experience sustainability and history in every sip and bite.
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Day 4 - Choose your own adventure

Tuesday, June 2, 2026
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Explore a Small Village, Go Outlet Shopping, Take Another Cooking Class, Visit Another Winery: The Choice is Yours!

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General

We only ask that there is a minimum of 4 people per activity.

Day 5 - Enjoy the Villa and Nearby San Casciano

Wednesday, June 3, 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 - Olive Oil Mill Tour and Tasting Experience

Thursday, June 4, 2026
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Olive Oil Sensory Experience

Frantoio del Grevepesa

Dare to challenge your palate and your knowledge. Are you able to recognize when an oil is a true extra virgin? We will guide you through the tasting of 3 oils, revealing their strengths and weaknesses, enriching your understanding of high-quality oil.
Fun and Taste: We promise an interesting and above all fun experience!
At the end of the tasting, treat yourself to a fettunta with good oil, enhancing the authentic taste of extra virgin olive oil.

Come and discover the art and passion that we put into every drop of our oil. We are sure that you will come away enriched and with a refined palate to recognize authentic quality.

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Day 7 - Cooking class

Friday, June 5, 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, June 6, 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. Azienda Agricola Casa Emma

Strada Provinciale Castellina in Chianti, 3, 50028 Barberino Tavarnelle FI, Italy

4. Fattoria Corzano and Paterno

Via S Vito di Sopra, 50020 San Casciano in Val di Pesa FI, Italy

5. San Gimignano

53037 San Gimignano, Province of Siena, Italy

6. FRANTOIO DEL GREVEPESA

VIA PROVINCIALE CHIANTIGIANA SULLA GREVE 6, 50026 San Casciano in Val di Pesa FI, Italy

Book With Us

Costs & Inclusions
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You are one click away from the vacation of a lifetime!

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Trip Cost - from $2,000 shared room

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.

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Inclusions

  • 8 days, 7 nights in a farmhouse villa

  • 3 chef-prepared dinners at the villa

  • 3 activities: wine tasting, cheese tasting, and olive oil tasting

  • 3 rental cars for up to 12 people to share

  • Welcome reception with wine and aperitivi

  • Shop the weekly outdoor market

  • Cooking class in an ancient kitchen

  • Local tourist tax

  • Travel planner and on-site retreat leader

  • Up to 2 group Zoom calls with the travel planner

  • Up to one hour of consultation time with the travel planner

  • Group circle chats with a life coach

  • Plenty of nourishing free time to nap, journal, read, wander, stargaze, etc.

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Exclusions

  • Airfare

  • Travel Insurance

  • Meals and activities not specified in the travel package

  • Wine and alcohol

  • Additional consultation time with the travel planner

  • Gratuities

  • Personal expenses

Accommodations

Rooms
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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.