WElcome To your Truly Tuscany Experience!
Escape to the heart of Tuscany for an unforgettable retreat experience. Set amidst the rolling hills and vineyards of the Tuscan countryside, Truly Tuscany Retreat offers a week-long journey of relaxation, exploration, and indulgence.
Our retreat is held at a beautiful and luxurious accommodation owned by close family friends. Villa Antica Sosta located on a hill above Castelfiorentino, south of Florence. The villa is a perfect place to relax and enjoy the stunning Tuscan scenery.
The villa offers the perfect setting for your group getaway. Boasting 5 bedrooms, 3 shared bathrooms, a spacious dining and family room with a fireplace and TV, our villa is the ideal place to relax and enjoy quality time with friends and family. The kitchen is fully-equipped and perfect for cooking as a group, including a cooking class.
Highlights are exclusive hiking through the Tuscan hills with an expert guide, a cooking class in a tiny borgo surrounded by vineyards, and unforgettable wine-tastings with special friends of Truly Italy. We'll be visiting towns like San Gimignano, Montefioralle and a majestic church called San Galgano.
Aug 30 - Sept 6, 2025
Availability : 4 double bedrooms
(1 bedroom has 2 single beds)
Retreat Cost:
$7891 - Double Occupancy (cost per guest per shared room)
+$200 - Single Occupancy
Space Available for 6 Travelers
Itinerary*
Day 1: Arrival and Welcome
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Transfer from Train Station
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Check-in at the Villa after 4 pm
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Evening: Welcome Aperitivo with wine and appetizers to start the retreat on a high note.
Day 2: The Essence of Tuscany
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Morning breakfast at the Villa
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Visit to L'Argento Firenze Silversmith factory and shop for a unique piece of an artisan craft to take home.
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Excursion to La Pia in Percussina for a Wine-Tasting & Tour
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Afternoon at leisure - explore the surroundings or relax by the pool
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Dinner prepared by our onsite Chef, showcasing local & unique flavors
Day 3: Adventure in San Galgano
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Breakfast at the Villa
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Day trip to San Galgano with a morning hike to invigorate the senses
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Lunch in the quaint town of Chiusdino
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Free time back at the Villa for relaxation
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Evening dinner at the Villa, another chance to indulge in Tuscan cuisine
Day 4: Culinary Delights and Montefioralle
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Breakfast at the Villa
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Day trip to the charming borgo of Montefioralle
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Immersive Cooking Class and lunch with an expert Chef in his home
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Afternoon wine-tasting against the picturesque Montefioralle
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Return to Villa Antica Sosta for a festive pizza party dinner
Day 5: Free Day in Florence
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Morning breakfast at the Villa
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Transfer to the Train station for a free day in Florence or another chosen destination to explore at your leisure
Day 6: Nature's Call in Gambassi Terme
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Breakfast at the Villa
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Transfer to Gambassi Terme for a guided hike and swim, connecting with nature
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Lunch in Gambassi to taste the local cuisine
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Dinner at a local restaurant, savoring the flavors of the region
Day 7: Exploring San Gimignano
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Breakfast at the Villa
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Transfer to the medieval town of San Gimignano for a day of exploration, shopping, and sightseeing
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Visit Casa Lucii for a memorable wine-tasting & lunch experience
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Spend the final afternoon at leisure - hike, swim, or take a well-deserved nap
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Farewell dinner at the Villa to celebrate the journey
Day 8: Ci si vede...See you soon!
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Morning breakfast at the Villa
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Check out by 10 am
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Transfer to the Train station for your departure, taking memories of Tuscany with you
Reserve your spot today for an unforgettable retreat experience amidst the beauty of Tuscany!
*The itinerary is subject to change to ensure the best experience for our guests.
We travel not to escape life but for life not to escape us.
Pictures of Villa Antica Sosta
What's included?
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Accommodation for 6 days/7 nights in a private villa with exclusive pool & garden
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All meals at the villa
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4 bedrooms & 3 shared bathrooms
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Pizza Party made with a wood burning oven onsite
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3 Wine-tastings & tour of a small, family run vineyard
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A visit to one of the oldest churches in the Florentine diocese
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A hike along a river where we can take a dip in fresh water.
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Access to a fully stocked kitchen throughout the week
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All excursions including wineries
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Tuscan Hike and a tour of San Galgano
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A visit to a family fun jewelry workshop near Chianti.
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Italian Cooking class and Lunch
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Transportation to/from each excursion by private car & driver
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Pick up/drop off at the Castelfiorentino train station
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Visits to cities like Florence, Greve in Chianti, San Gimignano, Siena, Montefioralle, San Casciano Val di Pesa
What's NOT included?
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Airfare
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Travel Insurance
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Meals outside of villa including a dinner at an authentic Family Run Restaurant
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Transport from/to airport
Our Authentic Touch
We speak Italian
Katie has been traveling/living to Italy for over 20 years. She speaks fluent Italian. Stefano, her Florentine husband, will be on this adventure with us as our driver and expert cook for the week. He'll make you laugh and help you understand his culture with stories.
Small Group Travel
Truly Italy prides itself on being focused on small group travel. Our goal is creating unique, authentic, bespoke Italian experiences that you will never forget. We seek out experiences you would not choose on your own. Welcome to authentic Tuscany!
Italian Family
You'll be among family while you are with us. No big coach buses. No tour guides holding a huge flower to follow.
Italy Experience Guide, Katie & Stefano are ready to fill your bellies with delicious Italian dishes.
We'll enjoy intimate dinners where we'll reminisce on our day exploring the hidden treasures of Tuscany.
traveling is about finding those things you never knew you were looking for
About the Hosts
Kate Portanova
Italy Experience Guide & Designer
Ciao! I'm Katie born in the US but my heart has remained in Florence.
I’ve got almost 20 years under my belt of taking trains, buses, and visiting the most beautiful, secluded places in Italy. In order to live in Florence legally, I went as far as getting UK citizenship to obtain residency in my most favorite city in the world. It was well worth the wait. My heart leapt with joy once I made Florence my permanent home from 2009-2013.
Since moving back home, my goal has been to keep Italy in my life any way possible, and thus, Truly Italy was born!
The Trick to getting through life is always having a holiday to look forward to.
One Activity a Day
Small Group Travel
Family Atmosphere
Authentic Italy
Each day consists of one activity, i.e. a visit to a small town, family run vineyard, a hike or a bike tour.
With plenty of free time, you can take a stroll through the Renai neighborhood, taking photos of the stunning scenery, and experience the serenity of the Tuscan hills.
After a Truly Italy retreat, you’ll feel connected, grounded, and recharged.
Ready for your fully planned Tuscany adventure with an Italian insider?
Reserve your spot today!!
"Nothing except time is wasted in Italy"
-Thomas Bailey Aldrich
