Together in Tuscany

Janine O'Rourke, owner of Together in Tuscany

Explore, savor and connect with the landscape, food, wine, people and culture of Italy. Join us for an authentic, slower-paced, villa-based, small-group women's retreat in the Tuscany countryside.

Women are often so busy taking care of others, that even on vacation they are usually in caretaker mode.  When you’re on one of our women’s retreats we will take care of YOU!  You will be pampered with your own chef, fully planned itinerary, drivers to take you everywhere and the chance to enjoy fun, immersive activities with other like-minded women.

Our philosophy is to provide the care and pampering that all women deserve in the beautiful setting of the Tuscany landscape.  We know that there is something different and uplifting about traveling with a group of women, especially women over 50.  I’ve felt it and if you’re a woman, I’m sure you have too.  Women provide each other with support (yes, you NEED that hand bag!), encouragement (I KNOW you can ride that e-bike, walk up that hill, etc.), and wisdom  from their own life experiences. 

Women want to have fun together. They want to let their hair down, be their authentic selves and savor each moment without having to worry about anyone else.

Our retreats provide the perfect setting for women to do all of these things while connecting with each other and immerse themselves in Tuscany with meaningful experiences.

Together in Tuscany

Was founded in 2022 by Janine Pisani O’Rourke. A Human Resources executive turned Tuscany dream-granter, Janine is also a transformational coach. She is inspired by the power of connection and cherishes her family, friends, and Italian heritage. Whenever in Italy, her senses come alive, and she feels at home as a third-generation Italian. Therefore, she brings guests to Tuscany to share its art, history, food, wine, and welcoming people.

Years of Experience and Local Partnerships

Together in Tuscany is the result of years of corporate experience and crafting memorable trips abroad. Additionally, a magical Tuscany villa vacation with family and friends inspired this venture. We’ve formed strong relationships with local partners in Italy, many of whom are women-owned. They are the best in their business and share our values. We understand what guests seek in a slower-paced vacation and aim to deliver a truly memorable experience.

All-Inclusive Women’s Retreats

We take care of all the details to offer women a vacation full of new experiences, bonding, and personal discovery. Our trips are all-inclusive with a thoughtfully planned itinerary. We ensure time for connection and reflection throughout the retreat.

What Sets Us Apart

What sets us apart from other retreats is our very small group size of six women per retreat. We stay in beautifully restored, ancient villas for the entire 7 nights. The group will have their own private drivers and personal chef. As the owner of Together in Tuscany, I will personally be there with the guests. Our small group size fosters genuine connections among the women. Our retreats are held in Tuscany and Umbria.

Certified B Corp

Single Supplement Policy

In keeping with our “pampering” philosophy, we provide 6 single rooms for women to stay with their own private bathrooms. Most women want their own room, especially women over 50, so we price our rooms based on single occupancy. However, if 2 women want to share a room, we do provide a shared room discount.

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