Tuscany has long seduced travelers with its medieval and Renaissance architecture, rich art history, and culinary treasures. This eight-day journey brings a deeper sense of cultural connection to the region through one-of-a-kind experiences that highlight its people, heritage, and craft.
Part of Exodus Adventure Travels’ new Signature Collection, Signature Italy | Allure of Renaissance Tuscany unfolds at an immersive pace, led by a handpicked Signature Guide who opens doors rarely accessible to visitors. Art and architecture tell stories of centuries past in Florence and Siena, explored through Signature Experiences such as jewelry-making workshops and a hands-on Tuscan cooking class.
In the countryside, Tuscany reveals itself through taste and tradition, with Signature Experiences that include truffle hunting with a local family and visiting a farm where cheesemakers still make pecorino by hand. Designed for those who want to understand Tuscany’s true essence and travel more meaningfully, this itinerary explores the region as you’ve never seen it before.
Itinerary
PLAN YOUR TRIP
Castello di Gargonza
Courtesy of Exodus Adventure Travels
Day 1: Welcome to Tuscany
After a complimentary road transfer from Florence, make yourself comfortable at Castello di Gargonza, a restored, privately owned medieval village located in the Tuscan countryside. Every Exodus Signature Stay boasts rich local character, and this historic castle hotel, dating to the 13th century and overlooking the iconic, fertile Val di Chiana, is no exception.
Join your Signature Guide for an introductory tour of the village, strolling down cobblestone paths and ascending the 14th-century tower where the poet Dante spent part of his exile. In the evening, gather for a welcome reception in the garden followed by an intimate dinner.
Join your Signature Guide for an introductory tour of the village, strolling down cobblestone paths and ascending the 14th-century tower where the poet Dante spent part of his exile. In the evening, gather for a welcome reception in the garden followed by an intimate dinner.
Olives growing in a Tuscan field
Courtesy of Exodus Adventure Travels
Day 2:Taste Artisanal Olive Oil and Explore the Town of Arezzo
Start the morning at Buccia Nera, a family-run estate where vineyards and olive groves run through the hills of Arezzo. Here, you’ll enjoy your first Signature Experience—curated moments that grant travelers one-of-a-kind access to local traditions and stories—during a private olive oil tasting led by the gifted artisans who produce it. Lunch follows at Osteria Cuprena, where a seasonal menu draws directly from the restaurant’s garden, capturing the rhythms of the surrounding countryside.
In the afternoon, walk through the town of Arezzo itself, drifting from broad modern avenues onto medieval streets and pausing at landmarks like the Romanesque Santa Maria della Pieve church and the green lawns of Parco Il Prato. As dusk settles, the day concludes at Osteria dei Mercanti, where time-honored Tuscan hospitality and locally sourced ingredients come together for an atmospheric meal of pizza, fresh Mediterranean seafood, and stuffed pasta.
In the afternoon, walk through the town of Arezzo itself, drifting from broad modern avenues onto medieval streets and pausing at landmarks like the Romanesque Santa Maria della Pieve church and the green lawns of Parco Il Prato. As dusk settles, the day concludes at Osteria dei Mercanti, where time-honored Tuscan hospitality and locally sourced ingredients come together for an atmospheric meal of pizza, fresh Mediterranean seafood, and stuffed pasta.
Florence’s rooftops
Courtesy of Exodus Adventure Travels
Day 3: Discover the Florence Cathedral’s Roof Terraces and Visit a Private Restoration Lab
See Florence from a rare perspective on this immersive day, beginning with privileged access to the roof terraces of the Florence Cathedral. Guided by an expert, you’ll ascend above the crowds during this Signature Experience to trace the city’s story from above. Afterward, savor lunch at B-Roof, where you’ll soak up more sweeping views over the city.
The afternoon delves deeper into Florence’s creative legacy during a private restoration lab visit, during which you’ll learn how specialists painstakingly conserve historic tapestries, garments, and decorative objects. This behind-the-scenes visit embodies Exodus Signature Legacy—moments woven into every itinerary that create a positive and lasting local impact. Finish with a shared, aperitivo-style dinner at La Ménagère, an atmospheric, library-like space lined with botanical-themed books.
The afternoon delves deeper into Florence’s creative legacy during a private restoration lab visit, during which you’ll learn how specialists painstakingly conserve historic tapestries, garments, and decorative objects. This behind-the-scenes visit embodies Exodus Signature Legacy—moments woven into every itinerary that create a positive and lasting local impact. Finish with a shared, aperitivo-style dinner at La Ménagère, an atmospheric, library-like space lined with botanical-themed books.
Tuscan wines
Courtesy of Exodus Adventure Travels
Day 4:Choose from Wine Tasting, an Italian Cooking Class, and More
This is a Signature Day, allowing travelers to select their preferred activity and to engage with Tuscany at their own pace through a curated, authentic experience. You might e-bike along quiet country lanes, stopping in an olive grove for bruschetta, honey, and local cheeses before a leisurely lunch rooted in seasonal produce. Or you can remain within the walls of Castello di Gargonza for a hands-on cooking class, learning to make fresh pasta with the castle’s chef.
Wine lovers can venture into Chianti for a tasting at a renowned winery. Art and design enthusiasts may decide to step inside a 14th-century palace in Cortona for a private introduction to the DelBrenna family’s centuries-old jewelry tradition. The evening is at your leisure—dine at the castle or follow your Signature Guide’s local recommendations—ensuring the day ends as thoughtfully as it begins.
Wine lovers can venture into Chianti for a tasting at a renowned winery. Art and design enthusiasts may decide to step inside a 14th-century palace in Cortona for a private introduction to the DelBrenna family’s centuries-old jewelry tradition. The evening is at your leisure—dine at the castle or follow your Signature Guide’s local recommendations—ensuring the day ends as thoughtfully as it begins.
Truffle hunting in Tuscany
Courtesy of Exodus Adventure Travels
Day 5: Go Truffle Hunting and Attend an Alabaster Demonstration
In the morning, head into the woods with a truffle-hunting family whose expertise has been passed down through generations. Accompanied by their trained dog, you’ll learn how to find and judge prized truffles before sitting down to a home-cooked lunch that celebrates the earthy delicacy at its freshest.
In the afternoon, continue to Volterra, an ancient hilltop city famous for its Etruscan history. Wander past its well-preserved Roman theatre and sweeping medieval piazzas. Gain insight into Volterra’s ancient artistic legacy, culminating in an alabaster demonstration that illustrates the transformation of the raw stone into exquisitely carved works in artisan workshops and museum collections. Return to the hotel with a relaxed dinner of regional Tuscan cuisine.
In the afternoon, continue to Volterra, an ancient hilltop city famous for its Etruscan history. Wander past its well-preserved Roman theatre and sweeping medieval piazzas. Gain insight into Volterra’s ancient artistic legacy, culminating in an alabaster demonstration that illustrates the transformation of the raw stone into exquisitely carved works in artisan workshops and museum collections. Return to the hotel with a relaxed dinner of regional Tuscan cuisine.
Pienza
Courtesy of Exodus Adventure Travels
Day 6:Visit a Pecorino Dairy Farm and the Ideal Renaissance City
After breakfast, drive to Podere Il Casale, a family-run farm outside Pienza, where a guided walk from stable to dairy offers an intimate look at daily farm life and the meticulous craft behind their celebrated pecorino cheeses and estate wines. A seasonal, farm-to-table lunch follows.
In the afternoon, stroll through Pienza, redesigned by Pope Pius II and considered the ideal city of the Renaissance, where masterful urban planning—from harmonious piazzas to sweeping countryside views—embodies Tuscany at its most refined. The journey continues to Montepulciano for a relaxed stroll through its historic center, ending in a traditional cantina where a light dinner pairs with a curated tasting of the region’s renowned wines.
In the afternoon, stroll through Pienza, redesigned by Pope Pius II and considered the ideal city of the Renaissance, where masterful urban planning—from harmonious piazzas to sweeping countryside views—embodies Tuscany at its most refined. The journey continues to Montepulciano for a relaxed stroll through its historic center, ending in a traditional cantina where a light dinner pairs with a curated tasting of the region’s renowned wines.
Siena’s medieval brick architecture
Courtesy of Exodus Adventure Travels
Days 7 and 8:Tour Siena’s Architecture
In the morning, an expert-led walk unveils Siena in rich detail, from the graceful curve of Piazza del Campo to the cathedral’s intricately patterned marble. Lunch is a highlight: a private invitation to dine inside the medieval Torre di Roccabruna, where a four-course meal is served high above the city with sweeping views across the rooftops and surrounding hills.
Back at Castello di Gargonza, the journey concludes with a farewell dinner in a medieval wine cellar and garden terrace, where chef Davide Canella’s seasonal Tuscan three-course menu and local wine pairings offer a fitting final celebration. The following morning allows time for one last coffee or a slow walk through Gargonza’s courtyards before departing for Florence.
Back at Castello di Gargonza, the journey concludes with a farewell dinner in a medieval wine cellar and garden terrace, where chef Davide Canella’s seasonal Tuscan three-course menu and local wine pairings offer a fitting final celebration. The following morning allows time for one last coffee or a slow walk through Gargonza’s courtyards before departing for Florence.