Your guide will welcome you at Camucia–Cortona train station for a smooth transfer up to your hotel in Cortona (Villa Marsili). In the afternoon, we’ll meet at our shop on Via Dardano 54—about a 10-minute stroll through the historic center—before setting off on a golden-hour e-bike ride around this timeless hilltop town. The highlight is sunset from Cortona’s most breathtaking viewpoint, followed by a curated pizza tasting selection to celebrate your first evening in Tuscany.

Activity: Guided eBike sunset tour (8/12mi | 3.5/4h) 
Meeting point: Via Dardano 54, Cortona at 5:30pm
Meals included: Pizza tasting + Drinks

This morning we’ll transfer to Pienza, the gateway to Val d’Orcia—one of Tuscany’s most iconic landscapes. We’ll time the start around the weather, with an early pickup recommended on warmer days. We’ll ride to hidden viewpoints and postcard panoramas, with ice-cold water provided for comfort.

At lunchtime, we’ll slow down in a cozy panoramic gazebo near Montepulciano for a tasting at an award-winning cheese farm: Pecorino and local specialties, paired with Vino Nobile di Montepulciano. Afterward, we’ll transfer back to Villa Marsili for some downtime.

In the late afternoon, the appointment is in the historic center for a hands-on cooking class: fresh pasta and sauce, then dinner together, perfectly matched with Cortona Syrah.

Activity: Guided eBike tour in Val d’Orcia (12/19mi | 4.5 / 5h); Cooking class with local chef (3.5 / 4h)
Meeting point: Pick-up at Villa Marsili at 8:00 / 8:30am; Piazza della Repubblica, Cortona at 5:30pm
Meals included: Lunch with Pecorino tasting; Hand made pasta, second course and dessert all this with Cortona’s Syrah.

This morning we’ll pick you up for a short transfer down into the valley, halfway between Cortona and Montepulciano. From there, we’ll ride through the rolling countryside of Val di Chiana on quiet gravel roads, weaving between silver olive groves and vineyard rows of Sangiovese and Syrah—pure Tuscany, calm and cinematic.

At lunchtime, we’ll return to the same small, welcoming winery for a four-course meal paired with their wines—cozy, unhurried, and beautifully local. After a little downtime back at the hotel, the afternoon shifts from countryside to culture: a guided walking tour through Cortona’s hidden corners and Etruscan layers, full of stories, history, and fun details you’d never find on your own.

Tonight we’ll celebrate with a final dinner together in one of Cortona’s best restaurants—warm hospitality, great food, and the perfect closing to the journey.

Activity: Guided eBike tour in Val di Chiana (9/17mi | 4.5 / 5h); Cortona walking tour with tour guide (2h).
Meeting point: Pick-up at Villa Marsili at 8:30am; Villa Marsili at 5:30pm.
Meals included: Lunch with four Wines tasting; Restaurant dinner at La Bucaccia or Osteria del Teatro (Cortona) at 7:30 / 8:00pm.

Enjoy a free morning at Villa Marsili up to your late check-out time. Sleep in, linger over breakfast, take one last stroll through Cortona, or simply soak in the view—no rush today. When you’re ready, we’ll transfer you back to Camucia–Cortona train station, with train tickets included onward to Florence or Rome.

Meeting point: Transfer to the railway station
Meals included: Breakfast