Tuscan Countryside Women's Retreat

Join us for an unforgettable week in Tuscany’s famed Val d’Orcia, where rolling hills, world-class wines, and a warm sense of connection await. This carefully curated women’s retreat offers the perfect blend of relaxation and discovery, all set within a beautiful private villa just outside the charming town of Montalcino—home to the legendary Brunello wines.

Guests will enjoy gourmet meals prepared by our private chef, exclusive excursions to some of Tuscany’s most beloved towns, and immersive cultural experiences that go far beyond the typical tourist path. Whether you’re traveling solo, with a friend, or to celebrate a milestone, this retreat is designed to help you slow down, savor the moment, and experience Italy like never before.

What to Expect:

• Elegant accommodations in a private villa with breathtaking views and generous common spaces for gathering.
• Curated cultural experiences including wine tastings, local market visits, artisan workshops, and a hands-on cooking class.
• Gourmet cuisine featuring meals prepared by a private chef.
• Time to unwind with spa options, optional yoga, and leisurely afternoons by the pool.
• A supportive and joyful group setting, with plenty of shared laughter, storytelling, and unforgettable moments.
• Excursions to Pienza, Montepulciano, Siena, San Gimignano, and Montalcino, with expert guides and time to explore at your own pace

This trip is intentionally designed to balance adventure and rest—offering you the chance to experience Tuscany in a way that’s both luxurious and deeply personal.

What’s Included: 

• Accommodations: Week-long accommodations in a charming Tuscan villa located in the Val d'Orcia area of Tuscany
• Transportation: Transportation for all included tour excursions and roundtrip transfers between our original meeting location in Florence and the villa
• Trip Host: A Dovetail Travel host accompanies the group throughout the journey
• Select Meals: Daily breakfasts, 7 dinners , cocktails and food experiences noted in the itinerary
• Wine and beverages: Served during meals prepared at the villa and at winery tours
• Tours + Activities: Organized group tours and activities specified in the travel itinerary

Exclusions:

Participants are responsible for: 

• International airfare and transportation outside of tour itinerary
• Travel insurance: Required for all participants
• Airport transfers
• Custom "add-on" excursions or deviations from the trip itinerary
• Personal expenses such as snacks, additional gratuities and communication costs
• Select meals not listed in itinerary
• Alcohol outside of group meals and wine tours
• International airport departure tax, if applicable
• Gratuities

Note: Sharing a room is only available with someone you’re traveling with, e.g. a friend or family member. We do not match you with guests you don’t already know.

Meet Your Hosts

Maya Djurasovic – Founder, Dovetail Travel

Hello! I’m Maya, founder of Dovetail Travel and your host for this unforgettable Tuscan retreat. My connection to Italy runs deep—rooted in childhood visits to my sister’s home in Tuscany and nurtured by my passion for food, wine, and cultural discovery.

Originally from New York and now based in the Midwest, I bring a background in education, event planning, and project management—as well as degrees from Boston College and Columbia University—to the trips I design and lead. But more than anything, I love creating joyful, inclusive spaces where people feel comfortable, inspired, and connected.

Dovetail Travel was born from the idea of building strong bonds—between travelers, with locals, and through shared experiences that linger long after the trip ends. I’m so excited to share this incredible part of the world with you. Get ready for a week of learning, laughter, meaningful connection, and, of course, unforgettable food and wine.

Buon viaggio!

Kathy Perunic – Founder, New Tuscan Experience

Ciao! I’m Kathy, Maya’s sister and the founder of New Tuscan Experience. I’ve called Italy home for over thirty years and have spent nearly half that time crafting luxury travel experiences that go beyond the guidebooks.

As a Georgetown graduate fluent in Italian, I work closely with an incredible team of local chefs, guides, sommeliers, and artisans—people I’ve known and trusted for years. Together, we offer guests authentic, behind-the-scenes access to the culture, flavors, and rhythms of Italian life.

The villas we use have been recognized by Condé Nast Traveler and other leading travel publications for their beauty and amenities, and I take great pride in designing itineraries that feel personal, immersive, and rich with heart. From winery owners to cheese makers, every person you’ll meet along the way helps tell the story of Tuscany.

I can’t wait to welcome you and share the magic of “la dolce vita.” Let’s make memories you’ll never forget.

DAY 1 – Saturday | Welcome to Tuscany
Meet in Florence for a welcome lunch before traveling in comfort to our villa. On the way, we’ll stop for a stroll in the hilltop town of San Gimignano, known for its medieval towers and charming streets. Settle into your villa room, then join us for cocktails and a festive welcome dinner under the stars.

DAY 2 – Sunday | Villa Day + Wine & Cheese Tasting
Start with optional yoga or a slow morning, followed by a leisurely Sunday brunch. The day is yours to relax by the pool, wander the olive groves, or curl up with a book. In the afternoon, enjoy a guided wine and pecorino tasting with a local expert. That evening, our chef will lead a playful tiramisù-making session before another fabulous villa dinner.

DAY 3 – Monday | Pienza + Brunello Picnic
Today we’ll visit the Renaissance gem of Pienza, known for its stunning views and artisan food shops. After time to explore, we’ll head to a family-run Brunello winery for a private tasting and vineyard picnic. Back at the villa, unwind before our wood-fired pizza party and cocktail hour.

DAY 4 – Tuesday | Montepulciano + Cheese Farm
Explore the Renaissance town of Montepulciano with a private guide who will take us through its historic streets and into an ancient underground wine cellar. After free time to shop or grab lunch, we’ll stop at a local cheese farm for a tasting. Tonight, enjoy our Tuscan Barbecue Night at the villa.

DAY 5 – Wednesday | Montalcino + Cooking Class
Venture into the heart of Brunello country with a visit to a boutique winery for a cellar tour, tasting, and panoramic terrace lunch. After time to explore Montalcino, return to the villa for a hands-on cooking class, where we’ll prepare a multi-course feast together with our chef.

DAY 6 – Thursday | Siena Tour
Discover Siena’s rich history on a guided walking tour, including highlights like the Piazza del Campo and the story of the Palio horse race. After time to explore and have lunch on your own, we’ll return to the villa for some R&R before gathering for another elegant dinner.

DAY 7 – Friday | Choose Your Adventure
The final full day is yours to personalize. Choose from:

• A truffle hunting excursion with a local expert and his dogs, followed by a truffle-themed lunch
• A visit to a luxurious thermal spa for a relaxing soak, massage, or just quiet time in nature

In the evening, we’ll gather for a celebratory farewell dinner and a toast to a week of unforgettable memories.

DAY 8 – Saturday | Departure
After breakfast, our drivers will escort you back to Florence. Arrivederci—for now!

DAY 1 – SATURDAY – Welcome to Tuscany

We’ll gather in the heart of Florence for a welcome lunch before heading to our villa in private Mercedes vehicles with English-speaking drivers.

On the way, we’ll stop in San Gimignano—one of Tuscany’s most iconic hill towns—for a scenic stroll through its charming streets and striking medieval towers.

Upon arrival at the villa, you’ll have time to settle in and unpack. That evening, we’ll kick things off with music and cocktails, followed by a delicious dinner prepared by our private chef.

DAY 2 – SUNDAY – Unwind at the Villa

Start the day with a light breakfast and a relaxing yoga session.

We’ll then enjoy a decadent Sunday Brunch together, followed by leisure time to lounge by the pool, wander the olive groves, or simply soak in the surroundings.

In the afternoon, we’ll savor a guided tasting of award-winning local pecorino cheeses and Tuscan wines with a local expert.

Before dinner, our chef will lead a fun tiramisù-making session. Then we’ll sip cocktails on the patio and dine al fresco under the stars.

DAY 3 – MONDAY – Pienza + Vineyard Picnic

After breakfast, we’ll set off on a scenic drive to Pienza, a UNESCO World Heritage site known for its beauty and charm.

Enjoy time to explore, shop, and admire the panoramic views before we head to a family-owned Brunello winery for a private tasting and vineyard picnic.

Back at the villa, relax before the evening’s festive Pizza Party—complete with cocktails and wood-fired creations straight from the brick oven.

DAY 4 – TUESDAY – Montepulciano + Cheese Farm Visit

Today we’ll tour Montepulciano, a historic hill town filled with Renaissance architecture and stunning views. Our private guide will show us highlights, including an ancient underground wine cellar dating to Etruscan times.

After the tour, enjoy free time to wander, shop, and grab lunch on your own.

Later, we’ll stop at a local pecorino cheese farm for a tasting before returning to the villa for some downtime.

The evening brings our Tuscan Barbecue Night—great food, great wine, great company!

DAY 5 – WEDNESDAY – Montalcino + Cooking Class

This morning, we’re off to the famed Brunello wine region. We’ll visit a boutique winery for a cellar tour, tasting, and a relaxed lunch on their panoramic terrace.

After lunch, we’ll explore Montalcino, the historic hilltop town that gave Brunello its name.

Once back at the villa, we’ll wind down before a hands-on cooking class with our chef—wine in hand and laughter guaranteed—as we prepare a feast to enjoy together.

DAY 6 – THURSDAY – Siena Tour

After breakfast, we’ll visit Siena for a guided walking tour through its rich history and medieval streets. Learn about the legendary Palio horse race and its deep cultural roots.

You’ll have time afterward for lunch, shopping, or simply soaking up the city’s unique charm.

We’ll return to the villa for a little R&R before gathering for cocktails and another lovely dinner.

DAY 7 – FRIDAY – Choose Your Adventure

This is your day to do what speaks to you most!

Option 1: Truffle Hunting Join an expert truffle hunter and his dogs for a guided woodland walk to search for these culinary gems, followed by a truffle-themed lunch.

Option 2: Luxury Spa Day Head to one of Tuscany’s famed thermal spas to soak in the natural hot springs, book a massage, or just lounge in peaceful surroundings.

We’ll reunite in the evening for a farewell dinner and a toast to a week of unforgettable memories.

DAY 8 – SATURDAY – Departure Day

After breakfast, check-out is by 10:00 AM. Our drivers will escort you back to Florence, where you can continue your journey or catch flights home.

Arrivederci!