Planning a trip to Tuscany? Hiking in Chianti puts you on quiet trails through Chianti Classico vineyards, medieval borghi, and unspoiled hills — far from overcrowded bus tours. Discover the best routes, practical tips, and how to get there from Florence without a coach.
Discover self-guided and guided hiking & gravel cycling tours in Tuscany and Umbria. Via degli Dei, Florence to Rome, Val d’Orcia and more — with GPX tracks, luggage transfers, hotel booking and local experiences. From €19% service fee only.
Discover the best hikes around Florence and Tuscany — from Chianti Classico and Val d’Orcia to Casentino and the Crete Senesi. A local expert guide to walking in Tuscany.
Discover the Florence Francis Way cycling guide from Florence to Arezzo, exploring scenic Tuscan landscapes, charming villages, and the Arno River cycleway. Perfect for gravel bikers and hikers alike!
Discover Florence beyond the usual tourist spots with **Florence urban hikes**—the perfect way to explore hidden streets, scenic hills, and breathtaking viewpoints. Escape the crowds, uncover secret gems, and experience the city in an active and authentic way. Follow our expert-guided routes or customize your own adventure with Out of the Box Florence!
Explore the scenic wine trails of Carmignano, Tuscany, where history, culture and exceptional wines meet. Discover sustainable hiking routes with local guides in one of Italy’s oldest wine regions. perfect for wine lovers and adventure seekers
Explore the Bolgheri wine region, famous for its Super Tuscan wines, through scenic hiking trails that take you from vineyards to ancient forests and coastal views. Discover three unique hikes that combine wine tasting and the natural beauty of Tuscany. Book a private tour with Out of the Box Florence for an unforgettable experience
Explore the scenic hiking trails of Val d’orcia and savor the renowned brunello di Montalcino wine. Discover sustainable travel adventures is Tuscany’s UNESCO World Heritage landscape with detailed itineraries and local insights. Perfect for eco-conscoius travelers seeking immersive experiences. Book your tour with Out of the Box Florence today!
Discover the ultimate Wine Hiking experience in Chianti Classico. Explore scenic trails, taste exquisite wines and immerse yourself in tuscany’s rich heritage.
E-bike Experience From Florence to Siena along the Via Romea del Chianti. A great adventure for a full day expert ride or multi days by foot.
