(Photos from this trip are located here)
In late May and early June 2026, Europe Your Own Way welcomed travelers to Italy for what became an unforgettable two-week celebration of Tuscany’s culture, cuisine, wine, history, and breathtaking landscapes.
Our adventure actually began several days before Tuscany, when a small group joined me in Rome for a private pre-tour experience. Together we explored some of the Eternal City’s most iconic treasures, including the Colosseum, Vatican Museums, St. Peter’s Basilica, Piazza Navona, the Trevi Fountain, the Spanish Steps, and many of Rome’s hidden corners. Between fascinating history, incredible food, and plenty of gelato, it was the perfect way to begin our Italian adventure and get to know one another before heading north to Tuscany.
The Best of Tuscany
From our beautiful villa near Lucca, guests enjoyed a week that showcased Tuscany’s most famous highlights while only unpacking once.
We wandered through Pisa and admired the famous Leaning Tower before exploring charming Lucca. We immersed ourselves in the history and beauty of Siena, strolled through the UNESCO-listed center, and learned about the city’s famous Palio traditions.
One of the week’s most memorable days was our visit to the Cinque Terre, where some guests tackled the spectacular coastal hike while others explored the colorful seaside villages at a more relaxed pace. We reunited in Vernazza to enjoy breathtaking Mediterranean views and an unforgettable aperitivo overlooking the sea.
Food and wine were naturally at the center of the experience. We shared a hands-on cooking class, enjoyed delicious meals prepared by our villa chef, sampled local wines, and explored the medieval towers and winding streets of San Gimignano.
A full day in Florence allowed us to experience the artistic heart of Tuscany, from the magnificent Duomo to Michelangelo’s David. We finished the week with a wonderful day in Chianti, visiting family-run producers and learning about the traditions behind Tuscany’s renowned olive oils, balsamic vinegars, and wines.
By the end of the week, strangers had become friends, and many guests were already talking about returning to Tuscany.
The Journey Continues: Heart of Tuscany Wine & Culture
While some travelers headed home with wonderful memories, several guests chose to continue their Italian adventure and joined us for a second week in the heart of Tuscany. With one night extra between the 2 weeks, we chose to explore another city – Bologna, known as the gastronomy capital of Italy. It definitely did not disappoint and we enjoyed the time by eating fabulous meals and admiring the famous porticos.
From there, we made our way further South just over the border from Tuscany, at a villa in Umbria. This second week offered a slower, deeper immersion into the Tuscan/Umbrian lifestyle from our beautiful villa in Paciano.
We explored some of central Italy’s most picturesque towns, including Pienza, Montepulciano, Montalcino, Spello, Assisi, and Perugia. Along the way, we sampled regional specialties, visited local artisans and producers, and enjoyed countless opportunities to wander medieval streets and soak in the atmosphere.
Wine lovers were especially spoiled as we visited several outstanding wineries throughout the region. Tastings, cellar tours, and conversations with passionate producers provided a deeper appreciation for the traditions that make Tuscany one of the world’s premier wine destinations.
The culinary experiences were equally memorable. Guests participated in a hands-on Tuscan cooking class, enjoyed farm-to-table meals, sampled local cheeses and olive oils, and learned firsthand why Italian food is celebrated around the world.
One of the week’s most unique highlights was our truffle hunting adventure, where we ventured into the countryside in search of one of Tuscany’s most prized delicacies before celebrating our discoveries over a delicious lunch.
Throughout both weeks, there was plenty of time to relax by the villa pool, enjoy aperitivos with new friends, share stories over long dinners, and embrace the slower pace that makes Tuscany so special.
Arrivederci, Toscana
Over two remarkable weeks, our travelers experienced the very best of central Italy—from the ancient wonders of Rome to the iconic landmarks of Tuscany and the hidden gems found along its winding country roads.
Together we explored historic cities, climbed medieval towers, hiked coastal trails, tasted exceptional wines, learned traditional recipes, hunted for truffles, and created friendships that will last long after the trip ended.
Thank you to everyone who joined us for this incredible Italian adventure. Your enthusiasm, curiosity, laughter, and camaraderie made these tours truly special. We are already looking forward to our next journey together under the Tuscan sun.
As always, if this sounds like something you would enjoy, please don’t hesitate to reach out to me. I would be happy to repeat the route, either as is or with adjustments to suit your preferences. The Best of Tuscany has become an annual fixture on our travel calendar – let me know if you’d like to join the next scheduled trip. Make sure to check out some of the images from this trip in the website photo gallery!