Villa Retreats in Tuscany for Women Who Crave Connection, Culture and a Deeper Sense of Self

Experience the Joy of Living Fully in Tuscany, Umbria & Beyond

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Rediscover Yourself, Indulge Your Senses, and Live Freely

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 lifelong friendships in a supportive community. As a certified professional 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 lifelong 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.

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Our 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, your villa offers a serene escape and the launching pad for your journey of self-discovery.

What to Expect

We specialize in curated experiences that go far beyond typical tours. Our mission is simple: to make your Tuscan adventure deeply personal, joyful, and effortlessly relaxing. Our retreats are designed especially for those who are ready to slow down, connect, and savor life, Italian style. You will leave the retreat feeling restored, enlightened, and energized. We do this by providing the perfect blend of discovery and relaxation. From cheese, olive oil and wine making experiences, to exploring local markets, touring ancient villages and witnessing artisans at their craft, you will experience a full immersion into the culture and cuisine of this coveted region. Get your hands messy as you learn to make fresh pasta. Enjoy the peace and beauty of the villa, your home for the week. Get to know the locals: your chef, tour guides and drivers. We will be there with you every step of your journey.

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Who Our Travel Is For

We welcome all adult travelers and specialize in women-centered travel, especially for those navigating a new chapter in life (e.g., empty-nesters, retirees, widows), solo travelers and best friends seeking reconnection.

If you’re looking for a trip that’s safe, soulful, and rejuvenating, you’re in the right place.

Upcoming Retreats

(Click on each one for more information)

Portugal’s Hidden Treasures

May 9-16, 2026

Tuscan Traditions Creative Retreat

May 16-23, 2026

Under the Tuscan Spell

May 23-30, 2026

Unwind in Chianti, Tuscany

May 30-June 6, 2026

Wine & Wellness in Lucca, Tuscany

June 27-July 4, 2026

Wine & Wellness in Lucca, Tuscany

September 26-October 3, 2026

Sacred & Savory Assisi, Umbria

October 10-17, 2026

Unwind in Chianti, Tuscany

October 17-24, 2026

Retreat Booking Details

What’s Included

  • Villa accommodations: wake up to panoramic views from your an ancient villa

  • Exquisite cuisine: enjoy delicious breakfast, lunches, and luxurious chef-prepared meals using seasonal, local ingredients with a perfect wine pairing

  • Winery, olive oil, cheese tastings: tour family-run ancient cellars and farms and savor their creations; all the tours are private for just your group

  • 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 150 days and 120 days before retreat start date

  • Accepted payments: Credit Card (fees apply), Zelle, Venmo, or ACH transfer

  • Custom payment plans available

Still Wondering if This is for You?

You’ve scrolled through our website, but are still unsure 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.

  • 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.

  • 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.

  • 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.

  • 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.

Have more questions? Let's Chat.

Our Guests and Partners Say It Best

  • “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

  • "Janine organized a great trip that brought us all together. We strengthened old friendships and formed new ones."

    Tammy K.

    Virginia

  • "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

  • “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

  • "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

  • "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

  • "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

  • "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

  • "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

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