Villa Retreats in Tuscany for Women Who Crave Connection, Culture and a Taste of Italy
Feel inspired, discover what makes you come alive again, and return ready to live with intention.
Join us in Tuscany and beyond where your home is an ancient villa with panoramic views and your carefully curated itinerary enables you to travel intentionally, reconnect with yourself, and form friendships in a supportive community. As a certified life coach and travel planner, Janine infuses each journey with opportunities for local immersion, hands-on experiences, and heartfelt connection. Whether you are traveling solo, with a group of friends, or it’s your first time venturing to Italy, we will take care of you. On our retreats you’ll find space to experience ultimate self-care, make friends, and leave feeling refreshed and renewed, with lasting clarity.
This isn’t just another trip. It’s a journey of growth, joy, and self-discovery.
Where You’ll Stay
Our carefully selected villas are the catalyst for your transformation. Imagine waking up to a countryside view from your bedroom window that looks so much like a painting you have to pinch yourself to confirm it’s real. Somewhere near the kitchen, the scent of espresso mingles with the chatter of the other guests. Surrounded by rolling vineyards and olive groves, enjoy the peace and beauty of the villa, your home away from home.
What to Expect
Our retreats are designed to feel both beautifully curated and wonderfully effortless. From the moment you arrive, everything is thoughtfully arranged so you can relax, settle in, and simply enjoy being here.
You’ll stay in a charming Tuscan villa surrounded by vineyards and rolling hills, where mornings begin slowly with coffee, fresh pastries, and the soft sounds of the countryside. Days might include visiting local villages, meeting artisans and winemakers, enjoying long lunches, or taking part in experiences that connect you more deeply with the culture of Tuscany.
Evenings often become a highlight gathering around the table sharing meals prepared by our villa chef and a glass (or two) of Italian wine as the sun sets over the hills.
Our small groups create a welcoming atmosphere where conversations flow easily and new friendships form naturally. There is always space to join in, explore, and connect, while also having time to rest, reflect, or simply soak in the beauty around you.
Many guests arrive hoping for a memorable trip. What they often leave with is something even more meaningful: a deeper connection to Italy, to new friends, and sometimes even to themselves.
Who Our Travel Is For
Our retreats and tours are for women who are happy to slow down and embrace the rhythm of Italian life. They are curious, open-minded, and genuinely interested in the world around them. They love meaningful conversation, appreciate beauty and culture, and enjoy learning how other people live. Above all, they share a love for Italy’s food, wine, traditions, and the warmth of its people. Some arrive celebrating a new chapter or quietly seeking a midlife reset. What they often find here is connection, inspiration, and the joy of experiencing Tuscany alongside a small group of thoughtful, like-minded women.
Explore Our Retreats and Tours
Every year we host a limited number of women’s small-group trips to Tuscany and beyond that are designed in collaboration with our local destination partners.
Unless otherwise noted, all trips are fully planned, all-inclusive, and fully escorted.
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Women's Small-Group Tour of Portugals' Most Captivating Towns, May 9-16, 2026
Picture yourself wandering through the sunlit streets of Porto, Lisbon and Cascais, a glass of Port in hand, and the scent of the sea in the air. From a peaceful boat ride through the Douro Valley to shared meals that celebrate Portugal’s warmth and flavor, you’ll explore Portugal in a more relaxed and authentic way.
6 SPOTS LEFT!
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Women's Tuscan Traditions Creative Retreat, May 16-23, 2026
Step back in time where an ancient hamlet is your home for the week, still inhabited by the fifth generation of a noble family. It’s the perfect setting for this creative journey rooted in ancient traditions where you will learn block printing, jewelry making, watercolor painting, and maiolica tile painting.
5 SPOTS LEFT!
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Women's Wine & Wellness Retreat in Lucca, Tuscany, September 26-October 3, 2026
Immerse yourself in an authentic Tuscan experience that will leave you feeling recharged, more mindful, and with gratitude in your heart. Mornings begin with gentle yoga or a nature walk and evenings end with a chef-prepared meal.
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Women's Small-Group Retreat: A Taste of Chianti, Tuscany, October 10-17, 2026
In the heart of Northern Tuscany, in the Chianti region, we’ll stay in a villa surrounded by vineyards and olive groves. Days are filled with tasting local cuisine, cooking with local chefs, and scenic drives through golden hills. Evenings end with long dinners at the dining table.
2 SPOTS LEFT!
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Women's Tuscan Traditions Creative Retreat
Step back in time where an ancient hamlet is your home for the week, still inhabited by the fifth generation of a noble family. It’s the perfect setting for this creative journey rooted in ancient traditions where you will learn block printing, jewelry making, watercolor painting, and maiolica tile painting.
COMING OCTOBER 2026!
What’s Included
Villa accommodations: wake up to panoramic views from your an ancient villa
Exquisite cuisine: enjoy luxurious chef-prepared meals at the villa using seasonal, local ingredients
Winery, olive oil, cheese tastings: tour family-run ancient cellars and farms and savor their creations
Excursions to nearby villages: step back in time as you wander through ancient villages which could include Siena, Panzano, Greve, Pienza, Lucca, Cinque Terre, Pietrasanta, Assisi, Spello, Perugia, or Montepulciano, depending on where your villa is located
Private transportation: take in the sites of the magnificent countryside as you get whisked away to your excursions and picked up from the train station
Cook & connect: learn how to prepare ancient recipes in hands-on, chef-led cooking classes
Outdoor markets: explore the weekly markets where locals do much of their shopping for housewares, clothing and shoes; shop owners take their wares on the road and travel from village to village a different day of the week
Space to reconnect with yourself: experience the transformative power of what we refer to as the “Tuscany Spell”, which has been known to reduce stress, promote relaxation, and help you connect with your inner peace
What’s Not Included
Airfare
Travel insurance
Meals outside of what is specified in the package
Alcohol and wine outside of what is specified in the package
Travel plans before or after the tour
Personal expenses
Anything not specified in the package
Payments
$500 non-refundable deposit due at time of booking
Interest-free, non-refundable payments due 120 days and 90 days before retreat start date
Accepted payments: Credit Card (fees apply), Zelle, or ACH transfer
Custom payment plans available
Wondering if This is for You?
We get it. Considering a trip like this is exciting, but it also comes with some questions. Let’s explore what could be getting in the way of you considering this investment in yourself.
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We understand. It’s hard to put a price tag on the transformational experience you’ll have when you travel with us. What if you considered this an investment in yourself and essential to your well-being? Do you feel a shift in perspective?
We curate experiences that go far beyond typical tours. Consider that you’ll be traveling in intimate groups of 8-14 guests, which means more boutique experiences, private tours, flexibility, and more genuine connection with the other guests and the locals you’ll meet along the way. You will also stay in homes filled with history, beauty, and the comforts you deserve. You only have to unpack once. No hopping around from hotel to hotel.
Not to mention, only $500 is required for you to save your spot. The remaining balances are interest-free and due 150 and 120 days before the trip. We can also work you on a payment plan customized to your needs.
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You’re not alone. That’s why we offer and encourage you to schedule a 1:1 call with us so you can get to know us better and determine if this is right for you. Once our trips start to fill up, we schedule virtual meet-ups so you can get to know the other guests pre-trip and we can answer questions in real time.
And our personal touch doesn’t stop there. We are present when you arrive and accompany you for the entire retreat.
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When you’re on our retreats, you may be traveling solo, but you are not alone. You are part of a supportive community of like-hearted women. You will get to know the other guests through our pre-trip virtual meet-ups and WhatsApp group chat, so when you arrive, you will already see some familiar faces. We’ll welcome you warmly, whether you arrive with a friend or are traveling solo.
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It could be daunting navigating international travel, especially if you’re traveling solo. We will guide you to determine the best airport to fly into, the best flight times, and if needed, how to purchase train tickets in advance. If you want to visit Florence or Rome before joining us in Tuscany, we can help with that too. Our drivers are there to meet you at the pick-up point and take you to the villa. As seasoned international travelers, we are experts at the logistics and will help you get there.
Our Guests and Partners Say It Best
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“I experienced the magic of Tuscany with a group of wonderful women. Janine curated a luxurious vacation for us, inclusive of unique experiences that were personalized to our group, and she made sure we had whatever we needed while on the trip. What’s more is that everything was taken care of - I didn’t have to do any of the planning which saved a lot of time and heartache! This was a one-of-a-kind experience that I’m grateful to have had!"
Christine D.
Virginia
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"Janine organized a great trip that brought us all together. We strengthened old friendships and formed new ones."
Tammy K.
Virginia
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"My trip in May 2024 was truly fabulous! Janine handled everything seamlessly and ensured our comfort throughout our time together. Our villa was nestled amidst the estate's vineyard and olive groves and was simply beautiful. Unlike my typical travel planning, all I had to do was show up, explore charming towns, markets, and museums, and savor relaxing dinners at the villa. It was an unforgettable experience!"
Cindy S.
Virginia
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“I miss all the wonderful women, the wine, the laughter and the great friendships that were formed. I want to go back! I will never forget this trip!"
Benette P.
Colorado
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"What a special trip! Thanks Janine for your hard work to make it happen and to all the women brightening the journey. I love the encouragement of women friendships."
Kathy S.
Virginia
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"What a beautiful experience! It was a true pleasure for Antonella and me to cook for your lovely group. We worked hard, yes, but always with joy, thanks to the warm and cheerful atmosphere you created. Your group is full of heart, humor and kindness. And you, Janine, were the soul of it all: attentive, well-organized, precise, and always with a smile. Thank you for your trust, your energy and all the good vibes."
Anna and Antonella
Tuscany villa cooks
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"I had such amazing experiences on this retreat! A great opportunity to connect with old and new friends. As a previous B&B/retreat owner and many years spent in the industry, I can say that this retreat was well beyond my expectations and I sincerely wish for folks to just jump in and follow your heartstrings. The food, the ambiance and all the memories with our hosts, facilitators and new comrades (including tour guides) equates to a 10+++. As much as I loved my own retreat chalet, this was on a whole different, unique and fabulous level! Janine, Monica and Laura blended their incredible talents to create magic with this “Yoga on Italy” retreat!
Susan W
Maryland
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"As a solo traveler, I was so impressed with Janine's passion of creating a safe, enjoyable wellness and travel experiences for silver aged travelers. Our excursions were well organized and informative. My favorite part was hiking the high stone steps in Cinque Tera. It was a personal fitness victory for me that I never would have experienced without this trip. Janine has the unique ability to lead while also enjoying herself. She loved being with all of us and it showed. There was never a time where I didn't feel included and valued as a participant even though most of the other women knew each other. The villa in Tuscany, Laura, our host and her staff were OUTSTANDING. The food was so delightful and all fresh, of course, my room was perfect. The cab drivers, the cooks, the massage therapists were all top notch. I highly recommend Together in Tuscany."
Janine C
Colorado
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"I would recommend this trip to anyone looking to spend a week together with like minded women. The experience included a balance between visits to local wineries, touring a few lovely villages, walking, biking, hiking, yoga, cooking class, swimming, boat rides, shopping and an optional opera! There was also time available to relax at the villa and have a massage. The vegetarian food was amazing."
Barb M
Virginia
Want more information?
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