Walking Adventure Tours & Trips in Central Italy
Explore a wide diversity of walking adventure tours through Central Italy. We have 15 adventures that vary from 5 days to 10 days. With the greatest number of departures in May, this is also the most popular time of the year.
10 best walking adventure Central Italy tours
Compiled by
MelissaCentral Italy travel expert at TourRadar
- A Taste of Italy: 8 Days - Value
- Local Living Italy - Tuscany San Gimignano
- Fantasia Italiana
- Christmas in Italy: Rome to Venice
- Tuscan Escape
- Florence & Tuscany Explorer - 5 days
- Rome's Finest: A Premium City Escape
- Geluxe: Italy: Tuscany and Umbria Vineyard Walks
- 6 Days, Italy by Train
- Geluxe: Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria
Duration 8 days Destinations Rome, Assisi, Siena, Florence, Pisa, Bologna, Venice, Montepulciano, Vatican City Age Range Ages 6+ Operator Omega Tours From
- US$1,564
Stay 5 nights at Casa Florelia agriturismo and walk the Via Francigena pilgrimage trail through vineyards for 2.5-3 hours of countryside trekking. Check out San Gimignano's medieval walls, Volterra's Etruscan heritage and alabaster workshops, then take guided walks through Florence and Siena.
Duration 7 days Destinations Florence, San Gimignano, Volterra, Siena Age Range Ages 12+ Operator G Adventures From $1,749
15% off- US$1,487
Duration 5 days Destinations Rome, Assisi, Siena, Florence, Pisa, Bologna, Venice, Tuscany, Montepulciano Age Range Ages 6+ Operator Omega Tours From
15% off- US$1,208
Walk through Pienza's cobblestone streets, a UNESCO site in Tuscany, then head to medieval Montepulciano for a tasting of the famous Vino Nobile wine. In Florence, you'll stroll across the Ponte Vecchio and climb up to Piazzale Michelangelo for views over the Arno River and city below.
Duration 9 days Destinations Rome, Pienza, Montepulciano, Siena, Florence, Venice Age Range Ages 12+ Operator G Adventures From $2,399
25% off- US$1,799
Duration 7 days Destinations Rome, Orvieto, Siena, Radda in Chianti, San Gimignano, Florence, Pisa, Lucca, Montalcino Age Range Ages 18-35 Operator Contiki From
25% off- US$1,639
Duration 5 days Destinations Florence, Siena, Cortona, Montepulciano, San Gimignano Age Range All Ages Welcome Operator On The Go Tours From $2,255
20% off- US$1,804
Duration 5 days Destinations Rome, Vatican City, Tivoli Age Range Ages 8+ Operator Omega Tours From
20% off- US$2,843
Geluxe: Italy: Tuscany and Umbria Vineyard Walks
“I will be talking about this trip for years to anyone who will listen. Could not be happier!”
Melissa, traveled in May
Walk the historic Via Francigena pilgrimage route from Abbadia a Isola to Colle Val d'Elsa, where ancient stone farmhouses and cypress-lined paths wind through Tuscany's rolling countryside. Trek the UNESCO-listed Val d'Orcia's Gladiator Trail from Pienza to the exact spot where Ridley Scott filmed.
No departure dates availableDuration 8 days Destinations Monteriggioni, San Gimignano, Colle di Val d'Elsa, Montefioralle, Panzano, Greve in Chianti, Siena, Pienza, Montepulciano, Città della PieveSee all destinations Age Range Ages 18+ Operator G Adventures 
Duration 6 days Destinations Venice, Pisa, Cinque Terre, Florence, Rome, Vatican City Age Range All Ages Welcome Operator Baboo Travel From
20% off- US$2,365
Trek the UNESCO-listed Val d'Orcia and walk the Gladiator Trail near Pienza, where Ridley Scott filmed those famous countryside scenes. You'll stay 7 nights in hotels and 2 nights in traditional agriturismos while walking through medieval Monteriggioni and crossing the Elsa River ankle-deep.
No departure dates availableDuration 10 days Destinations Florence, San Gimignano, Monteriggioni, Colle di Val d'Elsa, Montefioralle, Panzano, Greve in Chianti, Siena, Pienza, MontepulcianoSee all destinations Age Range Ages 18+ Operator G Adventures
