Ever wonder what it’s like to live la dolce vita? Let us whisk you away for a day in Tuscany on a Classic Journeys cultural walking tour—where every step reveals cinematic countryside views, every bite tells a story, and every moment feels like it belongs only to you. With our expert local guides leading the way, you’ll experience insider access to places and people that most travelers can only dream of. Curious? Read on for a glimpse of what awaits… andiamo!
Picture Yourself On Tour…
8:00 AM | Buongiorno with Espresso
Wake up to the Tuscan dream: a sunlit morning at your boutique villa hotel. As you sip your espresso and savor fresh melon and homemade almond cake, you might find yourself chatting with your gracious hosts—the Count and Countess themselves (pictured above).
9:15 AM | A Walk Through Time
With your walking shoes laced, join your expert guides on a walk where the air is filled with the scent of cypress trees. Along the way, you’ll pass an olive grove where a farmer is tending to his trees. Because your guides are all local, they stop to chat with him, sharing an impromptu insight into his life and work—a connection to the local people you know you’d never get on your own.
10:55 AM | The Abbey and Its Monks
Your walk leads you into Abbadia a Isola, an ancient village centered around its 11th-century abbey. Once a haven for pilgrims traveling along the Via Francigena, this was a place for rest and reflection. Like those pilgrims, you’ll pause here for a water break and short exploration of the abbey and its surroundings before continuing on your journey.
12:15 PM | Magical Monteriggioni
The plan is to continue walking along the Via Francigena toward Monteriggioni, one of Tuscany’s most perfectly preserved hilltop villages. The trail winds through rolling hills dotted with vineyards, offering breathtaking views at every turn. But just in case you’d like to shorten your walk, Massimo—your driver—makes a timely pass in his Mercedes Sprinter to whisk you ahead for some early shopping or an aperitivo before lunch.
1:00 PM | Lunch with a View
Lunch features regional specialties: perhaps pici pasta with wild boar ragù, creamy pecorino drizzled with local honey, or ribollita, a hearty Tuscan bread soup. Pair it all with a glass of Chianti or Vernaccia di San Gimignano as you soak in the panoramic views from this fortified gem.
2:45 PM | Farm-Fresh Flavors with Shepherdess Sarah
After lunch, you can opt for the perfect after-meal stretch—a scenic walk to Sarah’s family farm—or linger longer in Monteriggioni before accepting Massimo’s offer for a ride to Sarah’s. Either way, Sarah greets you warmly and walks you through her property, showing how she raises her animals and crafts her cheeses using time-honored methods. As curious goats and sheep look on, Sarah shares her passion for sustainable farming before inviting you to taste her creations accompanied by her family’s homemade honey.
5:15 PM | La Dolce Vita by the Pool
Back at your villa hotel, it’s time to embrace la dolce vita. Sip on an aperitivo as you relax by the infinity pool, where the water seems to melt into the rolling Tuscan hills. Maybe you even opt for a massage with a view of the vineyards.
7:45 PM | Buon Appetito!
Dinner tonight is pure Tuscan perfection—a feast of regional specialties at one of our favorite local restaurants. Share laughs and stories over fine wine and exquisite dishes prepared with heart and tradition.
9:55 PM | A Soulful Stroll Back to Your Room
As you wander back to your room under a sky full of stars, you glance at your Apple Watch—it buzzes to let you know you’ve hit your step count for the day. But you hadn’t noticed before now because your soul was buzzing even more—with joy from the people you met, stories you heard, and moments that made this day unforgettable.
This is just a taste of what makes our Tuscany & Cinque Terre tour so extraordinary—curated walks through cinematic landscapes, insider experiences with locals, and luxurious stays that feel like home (but better)! Ready to join us, on foot at eye level?
Explore Tuscany & Cinque Terre
