Women’s Retreat: Unwind in Chianti

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

Location: San Casciano in Val di Pesa (21 km South of Florence) with visits to nearby Siena, Panzano and Greve

Group size: 8-14 guests

Designed For: Women who crave experiential travel, connection, culture and a taste of la dolce vita

Fitness Level: Ability to walk on uneven surfaces and climb hills and steps

Pricing: All-inclusive packages starting at $4,799; only $500 due NOW

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.

Each day brings something new: a private wine tasting at a family-run vineyard sipping farm-to-table wine, an afternoon wandering a medieval village where time stands still, or the thrill of learning to make fresh ravioli and tiramisu with our villa chef. Evenings are spent sharing stories over long, leisurely dinners with delicious Tuscan cuisine and local wines that taste too good to be true.

This retreat is designed for women (typically those 50+) who crave connection, culture, and a touch of indulgence. Some women arrive solo, others bring sisters or lifelong friends, but all leave with new bonds, renewed energy, and memories that linger long after the suitcases are unpacked. Guests often describe the week as magical, soul-nourishing, relaxing, fun, and energizing.

Our villa is your sanctuary: comfortable and inviting, with cozy corners to journal or sip wine, sweeping countryside views, and private spaces for reflection. Beyond its walls, Tuscany calls you to explore, whether it’s strolling through Siena, watching how cheese is made on a family-owned cheese farm, shopping at the outdoor markets like a true local, or indulging in a cooking class in an ancient kitchen.

Don’t miss this chance to live la dolce vita. Spaces are limited, and once they’re gone, they’re gone. Reserve your place today and step into a week of beauty, connection, and unforgettable adventure in the heart of Tuscany.

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!

San Casciano Val di Pesa

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

Accommodations

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

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.

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.

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.

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.

Group of people standing outdoors on a gravel path with trees in the background, posing for a photo.

Terms & Conditions

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).