Tuscany & Umbria: A Curated Walk from Florence to Rome

After arriving in Florence, check into Hotel Club Florence, located near Santa Maria Novella. The first evening is best spent settling in. As the sun sets, the city's stone facades take on a warm glow, and a quiet walk through the historic center is the ideal way to get your bearings. Follow the route to dinner at a local Florentine restaurant, then conclude the night with a stop at a local gelateria—the pistachio and fiordilatte are the local standards.

The most efficient way to see Florence's dense core is with a local guide. A morning walking tour covers the essential landmarks: the Cattedrale di Santa Maria del Fiore (the Duomo), the political hub of Piazza della Signoria, and the jewel-box shops of the Ponte Vecchio. The tour concludes near a local market, a good place to find lunch. The afternoon is unscheduled. A classic option is the walk up to Piazzale Michelangelo for its commanding city view, best enjoyed with a drink as the sun lowers. Note that major museums are typically closed on Mondays.

The journey from Florence leads into the Tuscan countryside. The first stop is the medieval walled town of San Gimignano, where you can explore the architecture before lunch. The afternoon is dedicated to the first proper trek of the route. From the village of Strove, follow an eight-kilometre section of the Via Francigena pilgrim trail. The path leads to the Elsa River, where wading across the shallow, cool blue water provides a brief respite. The final stretch of the trail brings you into the historic town of Colle Val d'Elsa to stay at Hotel Palazzo Pacini.

Today's walk focuses on Monteriggioni, a perfectly preserved 13th-century walled fortress. A short transfer leads to the trailhead near the Chiocciola and Villa Castles. From there, the 8-kilometer path follows another section of the ancient Francigena way, winding through bush and pasture on dirt and gravel trails before arriving at the town's gates. After time to explore the ramparts and streets, lunch features local Tuscan flavors. The return to Colle Val d'Elsa leaves the afternoon free to explore its historic upper town or simply rest before dinner.

The itinerary moves into the Chianti Classico region, famous for its namesake red wine. The day starts in Montefioralle, a small castle town that serves as the trailhead. A 6-kilometer walk on dusty country roads winds through vineyards to the hamlet of Panzano. The destination is a specific one: Molino di Grace, a vineyard where a tour of the cellars is followed by a rustic lunch at their farmhouse. The afternoon includes a stop in Greve, the region's main market town, before checking into Borgo Casa al Vento, a villa property set among the vineyards near Gaiole.

The day is dedicated to Siena, one of Tuscany's great medieval cities, reached via a drive through the Chianti hills. Spend the morning exploring the historic center, taking in the scale of the fan-shaped Piazza del Campo and the details of the Duomo complex. After lunch at a Sienese restaurant, there is ample time to navigate the city's steep, narrow streets or browse for local crafts. The journey back leads to Borgo Casa al Vento, your villa base in Chianti. Here, the evening concludes with a four-course dinner, where each dish is paired with a different wine produced directly on the estate.

Today explores the Val d'Orcia, the iconic Tuscan landscape of rolling hills and cypress trees designated a UNESCO World Heritage site. The day begins with a transfer to Pienza, a Renaissance model town. A 6-kilometer loop walk starts here, descending into the valley past the Romanesque church of Corsignano. The route includes the Strada dei Gladiatori, the specific road used in a memorable scene from the film Gladiator. Back in Pienza, the walk is rewarded with a tasting of local pecorino and ricotta. The afternoon is spent in nearby Montepulciano with a local guide before crossing into Umbria for the night.

A day dedicated to the rhythms of Umbrian life. The morning is spent with a local chef for a hands-on cooking class. The focus is on regional specialties like handmade pasta, with the results enjoyed for lunch, accompanied by local wines. The afternoon offers a change of pace with a guided walk through Città della Pieve. The town is the birthplace of the Renaissance painter Perugino, and its maze-like brick alleys are a distinctive feature, built to defend against enemies and provide shade from the summer sun.

The final leg of the journey from Umbria to Rome takes approximately two hours. Upon arrival, plan for a three-hour exploration of the city, choosing between two distinct routes. One option is a classic walking route covering the essential sights of Rome, leading from the Spanish Steps to the Trevi Fountain and the Pantheon. Vespa travel offers a different perspective, featuring views of the Colosseum and winding through the streets of the Trastevere district. The evening includes dinner at a Roman restaurant before checking into Mama Shelter Roma, a design-led, contemporary hotel in the Prati district known for its rooftop bar.

The trip concludes this morning in Rome. There are no planned activities, allowing for a flexible departure. Private transfers to Fiumicino or Ciampino airports can be arranged from the hotel.