Unwind in Chianti

October 17-24, 2026

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This is YOUR time!

Nine women standing on a gravel pathway outdoors, smiling for a group photo, surrounded by trees and cloudy sky.

Dates: October 17-24, 2026

Duration: 8 days, 7 nights

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

Group size: 8-14

Who is This For: Women who crave connection, culture & self-discovery

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

Pricing: $4,799 per person shared room; only $500 due NOW

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 carnivore 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

Don’t miss this chance to step into a week of beauty, connection, and unforgettable adventure.

Limited Spots Available – Claim Yours Now!

This 7-bedroom villa is a show-stopper with it’s unbelievable location on the Villa Le Corti Estate, owned and still resided by the historical and esteemed Corsini family.  When you stay here you are immersed within the olive groves and vineyards of Principe Corsini. Their wine and olive oil are delicious and plentiful within the villa. With the estate so close, it’s only a short walk down the driveway to enjoy the fine dining at their Osteria, partake in a winery tour and tasting or get your hands messy in the chef-led cooking class.  

Why we love this villa: Its charm, its history, its proximity to Florence, the ability to walk into the town of San Casciano, the staff, the expansive areas to gather, the food, the on-site winery, the comfortable beds, and of course, the amazing views!  This beautifully restored 400-year-old farmhouse comes with a private swimming pool and stocked with Principe Corsini wine. Some mornings you may even catch a glimpse of the hot air balloons in flight!   

Here’s Where You’ll Stay: San Casciano Val di Pesa

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.
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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

A bedroom with two twin beds with vintage headboards and floral bedspreads, a wooden nightstand with a lamp, a chandelier, a window with wooden shutters, and a small rug on a wooden floor.

2 Shared Twin Rooms

A bedroom with two beds featuring floral headboards and white bedding, separated by a wooden nightstand with a lamp, under a wooden beamed ceiling, with a brick floor and additional seating furniture.

Shared Deluxe Twin Room

A bedroom with a bed that has a pink ornate headboard and floral bedding, stacked towels on the bed, a wooden bed frame step with a railing, a table lamp, a framed picture, and an opening leading to a room with another bed.

Standard King Room

Living room with two beige armchairs, a white coffee table, a wooden dresser with a lamp and glass bottles, framed profile silhouettes on the wall, and an arched doorway leading to a bedroom with a green bedspread.

King Suite

A vintage bedroom with wooden ceiling beams, a floral bedspread, a white chandelier, and antique furniture including two nightstands, a dresser, and chairs.

King Superior Suite

A cozy bedroom with a bed, two chairs, a small table lamp, and exposed wooden ceiling beams.

King Suite Exterior Entrance

Limited Spots Available – Claim Yours Now!

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.

  • 8 days, 7 nights in a farmhouse villa

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

  • Chef-prepared dinners at the villa

  • Private transportation to excursions

  • A carnivore experience with a famous butcher

  • Watch how cheese is made 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

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

  • Local tourist tax

What’s Included

What’s Not Included

  • Airfare

  • Travel Insurance

  • Anything not specified in the travel package

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

  • One lunch and 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).