8-Day Chianti Tuscany Villa Retreat Near Florence

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

May 30-June 6, 2026

Join us in Chianti!
Chianti Tuscany villa retreat vineyard view

This is your time to slow down and savor Tuscany.

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.

Tuscany Villa Retreat Details

Chianti Tuscany villa retreat vineyard view

When:

May 30-June 6, 2026

Where:

San Casciano in Val di Pesa (21 km South of Florence)

Group size:

8-14 women

Fitness Level:

Ability to walk on uneven surfaces, climb hills & steps​

Tuscany Villa Retreat Highlights

  • Taste the delicious pecorino cheese as you learn how the cheese is made at a family-owned farm

  • Experience a private tour and wine tasting on the villa’s estate where a noble family still resides

  • Cruise through the Chianti region on an e-bike with stops at a winery and medieval villages

  • Explore the ancient villages of Siena, Panzano and Greve where history comes alive

  • Indulge in a unique dining experience at a famous butcher’s restaurant

  • Walk from the villa into the town of San Casciano to shop the outdoor market and taste the creamiest gelato

  • Enjoy the thrill of hand-rolling pasta dough to make fresh ravioli with your villa chef in an ancient kitchen that feels like it should be part of a museum

  • Share stories, meals, and connection in an ancient villa surrounded by nature with farm-to-table Tuscan cuisine and local wines

Chianti Tuscany villa retreat private drivers
Chianti Tuscany villa retreat Siena village

This small-group Tuscany villa retreat offers the perfect balance of slow living, authentic food and wine experiences, and time to reconnect with yourself, with others, and with the soul of Italy.

Detailed Itinerary
A woman standing on a gravel street in a European village, smiling and holding a box of wine bottles, with buildings and greenery in the background.
A wooden cabinet with open glass doors displaying bottled wines on shelves inside.
A group of ten women standing on a gravel pathway outdoors, smiling and posing for a photo in a scenic area with trees, shrubs, and cloudy skies.
A group of people listening attentively to a guide inside a rustic winery cellar, standing near large wooden barrels with red wax seals.
Five women standing outdoors in front of trees, hills, and cloudy sky, smiling at the camera.
Mixed salad with leafy greens, roasted sweet potatoes, beans, and chopped vegetables on a white plate.
Woman in a denim jacket and black pants standing in a vineyard, reaching out to touch grapevine leaves, with rolling hills and a clear blue sky in the background.
Gugliaie king superior bath.jpg
Group of four women walking down a narrow, wet, cobblestone street in a European city, lined with old yellow and beige buildings with shutters and an ornate street lamp.
Four women standing outdoors on a gravel path, with a scenic green landscape of rolling hills and vineyards in the background. They are smiling and posing for the photo, with a decorative purple rooster silhouette next to a large wine barrel.
Gugliaie dining room.jpg
A group of eleven women and one man standing inside a warmly lit restaurant or cafe, with a rustic, vaulted stone ceiling, wooden shelves, and staircase in the background.
Guliaie living room.jpg
Group of people standing outdoors on a gravel path with trees in the background, posing for a photo.
Gugliaie aerial view.jpg
Gugliaie kitchen.jpg
Gugliaie outdoor terrace seating.jpg

Choose Your Room

Chianti Tuscany villa retreat bedroom with 2 twin beds

2 Shared Twin Rooms

$4,999 pp shared

Chianti Tuscany villa retreat bedroom with 2 double beds

Shared Deluxe Twin Room

$5,099 pp shared

Chianti Tuscany villa retreat bedroom with 1 king bed
Chianti Tuscany villa retreat bedroom with 1 king bed

Standard King Room

$4,999 pp shared

$5,599 pp single

Chianti Tuscany villa retreat bedroom with 1 king bed

King Suite Exterior Entrance

$5,099 pp shared

$5,699 pp single

King Suite

$5,099 pp shared

$5,699 pp single

Chianti Tuscany villa retreat bedroom with 1 king bed

King Superior Suite

$5,199 pp shared

$5,799 pp single

Note: Due to the old, historic nature of the villa, there are many sets of uneven stairs. Guests must be comfortable walking up and down uneven stairs and carrying their own luggage to their rooms.

Book Now!

  • 8 days, 7 nights in a farmhouse villa

  • All meals including 6 breakfasts, 4 lunches and 6 dinners (with wine)

  • Chef-prepared dinners at the villa

  • A unique dining experience at a famous butcher’s restaurant

  • Witness cheese-making at a family-run cheese farm

  • Shop the weekly outdoor market

  • Explore the Chianti region on an e-bike with stops at villages and a winery

  • Guided tour of Siena with free time to explore on your own

  • Cooking class in an ancient kitchen

  • Transportation to and from the Florence train station and the villa upon arrival and departure

  • Private transportation to excursions

  • Gratuities for the tour guides, drivers, cooks, housekeeping, etc.

  • Local tourist tax

What’s Included

What’s Not Included

Payments

  • $500 non-refundable deposit due at time of booking

  • Interest-free, non-refundable payments due 150 days and 120 days before tour start date

  • Accepted payments: Credit Card (fees apply), Zelle, Venmo, or ACH transfer

  • Custom payment plans available

  • Airfare

  • Travel Insurance

  • Anything not specified in the travel package

  • Wine and alcohol outside of what's included in the itinerary

  • Two lunches and one dinner

Cancellation Policy

A non-refundable deposit of $500 is required to secure your booking. Half of your trip balance is due 150 days prior to the trip start date and the remaining balance is due 120 days prior to the trip start date.  All bookings made within 120 days of the trip start date require full payment. 

We understand that plans can change and emergencies come up. However, due to the nature of our business, deposits and payments are applied to third party vendors very shortly after payments are received. As such, we have a strict no-refund policy with the following exception: if the trip is cancelled by Together in Tuscany, the guest will receive a full refund for all payments made.

Travel Insurance

We HIGHLY recommend that you obtain travel insurance. If you must cancel your participation in a Together in Tuscany trip for any reason whatsoever, including health conditions, death of a family member, travel difficulties, personal reasons, or any other reason whatsoever, the travel insurance can cover some or all of these expenses. 

Service Agreement

All guests are required to review and accept the Terms and Conditions outlined in the Service Agreement which will be provided upon booking your room. The Service Agreement addresses risks and liabilities for the Provider (Together in Tuscany) and the Purchaser (Guest).