Small-Group Immersive Retreats in Tuscany Villas
For mid-life women who crave connection, culture, and their own “Under the Tuscan Sun” moments
Come for the Tuscany dream. Leave feeling deeply connected.
Ciao, I’m Janine, life coach to mid-life women, travel planner, and your guide on this journey. I invite you to join me for an experience that goes far beyond travel. Each day is thoughtfully curated to help you slow down, savor the moment, and reconnect with yourself in a way that feels both grounding and expansive.
Through meaningful local experiences, hands-on moments, and plenty of space to simply be, you’ll find yourself naturally opening to the beauty around you, to new friendships, and to parts of yourself that may have been waiting patiently to be rediscovered.
This isn’t just another trip. It’s a return to yourself, to what matters most, and to the life you’re ready to step into next.
Schedule a call to begin your journey.
The Villas
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.
Explore Our Retreats
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![Porto Portugal]()
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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![Lucca Tuscany Italy]()
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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![Tuscany, Italy countryside]()
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.
SOLD OUT!
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![Tuscany village]()
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!
Wondering if This is for You?
We get it. Considering a retreat like ours 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.
Kind Words From Our Guests and Partners
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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
Avoid these costly mistakes while traveling to Italy.
Request a FREE TRAVEL GUIDE! Here you’ll find insider tips and secrets from seasoned travelers on how to avoid the common mistakes and regrets that too many travelers make. These tips will help turn your vacation into a truly restorative retreat.
Want to learn more?
Use our contact form to ask us anything. We’ll get back to you within 48 hours. We’re here to help you.
Together in Tuscany is registered under Breakthrough Consulting, LLC, a United States Company.
