Experience the beauty, flavors, and traditions of Tuscany on a journey through some of Italy’s most iconic hill towns, vineyards, and cultural treasures. From the medieval streets of Siena and San Gimignano to the rolling vineyards of Chianti and Montepulciano, this immersive experience combines world-class food and wine with authentic local traditions and breathtaking landscapes.
Along the way, you’ll enjoy private guided tours, cooking classes, winery visits, truffle hunting, thermal villages, and unforgettable meals that showcase the very best of Tuscany’s rich culinary and cultural heritage. The journey concludes in Florence, where Renaissance art, architecture, and timeless Italian charm come together.
Highlights
Explore the medieval treasures of Siena, San Gimignano, Lucca, and Florence
Visit renowned wine regions including Chianti and Montepulciano
Enjoy wine tastings in historic Tuscan wineries and castles
Experience a traditional Tuscan picnic overlooking the countryside
Discover the UNESCO-listed towns of Pienza and San Quirico d’Orcia
Relax in natural thermal springs and historic spa villages
Join a guided truffle hunt followed by a gourmet truffle dinner
Participate in a hands-on Florentine cooking class
Experience Florence’s famous wine windows and artisan traditions
Enjoy authentic Tuscan cuisine, local specialties, and regional wines throughout the journey
What’s Included
Accompanied travel with Phil throughout the journey
Hand-selected accommodations in Tuscany and Florence
Private transportation between destinations
Guided tours with local experts
Winery visits and wine tastings
Traditional cooking class and culinary experiences
Truffle hunting excursion and gourmet dinner
Cheese tastings and farm-to-table experiences
Personalized pre-trip planning and preparation
Travel app with itinerary details, confirmations, and tickets
Dedicated support before and throughout your travels
Access to authentic local experiences beyond the typical tourist route
