An intimate spring journey through vineyards, villages, and villa life in the heart of Southern Tuscany.
Slow down and savor Southern Tuscany at its finest during this luxurious, small-group women’s retreat. From the golden hills of the Val d’Orcia to the Brunello-producing vineyards of Montalcino, this villa-based escape blends elegance with authenticity.
Stay in a beautiful countryside estate, explore enchanting hill towns like Montepulciano and Pienza, feast on gourmet meals prepared by local chefs, and sip world-renowned wines right where they're made.
This isn’t just a trip—it’s a curated journey filled with laughter, connection, and the kind of beauty that lingers long after you return home.
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.
This trip is intentionally designed to balance adventure and rest, allowing you to experience Tuscany in a way that’s both luxurious and deeply personal.
Participants are responsible for:
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.
A note from Maya:
Hello! I'm Maya, the founder of Dovetail Travel a boutique luxury travel company specializing in trips to Italy which focus on creating meaningful connections through immersive experiences. I am thrilled to be your group leader for this unforgettable food and wine tour.
I have a passion for travel, cooking, and exploring other cultures and thanks to deep-rooted family connections, Italy holds a special place in my heart. A graduate of Boston College and Columbia University, with experience in event planning and project management, I specialize in creating warm, inclusive environments where everyone feels welcome.
The concept behind Dovetail Travel was born from the idea of building strong bonds—whether with fellow travelers or locals who share their culture. I am looking forward to creating lasting memories with you as we explore the wonders of Italy together. Get ready for an adventure filled with learning, laughter, and of course, delicious food and wine!
A Note from Kathy:
Hello! I’m Kathy, and for over thirty years, I’ve called Italy my home. I’ve worked in the travel industry for nearly fifteen years, meticulously curating luxury trips to Italy. As a Georgetown University graduate and the founder of New Tuscan Experience, Dovetail Travel’s literal and figurative sister company, I’ve dedicated my career to sharing Italy’s beauty and culture with others.
Fluent in Italian, I collaborate with a team of local professionals—top-rated guides, chefs, sommeliers, cooking school instructors, and drivers—who are experts in their fields and passionate about sharing their knowledge. The villas we use have been awarded the highest honors by renowned travel publications like Condé Nast Traveler, ensuring that our guests experience top-quality amenities, excursions, food, and wine. Every tour reflects my passion for Italy and my desire to share this enchanting country in a way that feels intimate, immersive, and full of heart.
Italy is renowned for its incredible cuisine and world-class wines, and I can’t wait to introduce you to the flavors and traditions that make Italian food and wine so special. Throughout our tour, you will have the opportunity to meet local artisans, taste exquisite wines, and savor authentic dishes that reflect the heart and soul of Italy. Come learn what makes life in Italy so sweet and discover "la dolce vita" for yourself!
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!
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!
