Florence is universally revered as the cradle of the Renaissance, a dense urban jewel box where the concentration of art per square mile is perhaps the highest on Earth. For millions of visitors the experience of the Tuscan capital is defined by the Uffizi Gallery, the shadow of Brunelleschi’s dome, and the crowded stones of the Ponte Vecchio. However, for a growing demographic of travelers, Florence serves a different purpose entirely: it is a premier trailhead.
Beyond the Reinassance City: Florence as a trailhead
Geographically, the city sits in a “conca” (basin) flanked by the rolling hills of Tuscany to the south and the formidable ridges of the Apennine Mountains to the north. This unique positioning makes it a natural hub for some of Europe’s most spectacular long-distance walking routes. In recent years there has been a palpable shift in Italian tourism. The frenetic pace of “checking off” landmarks is giving way to slow travel: a movement that prioritizes deep engagement with the landscape and local culture over efficiency.
Walking pilgrimages, or cammini, have exploded in popularity, drawing inspiration from the famous Camino de Santiago in Spain but offering a distinctly Italian flavor (defined by medieval hill towns, significant elevation changes, and a deep layering of history). The routes radiating from Florence require physical fitness, logistical preparation and a willingness to embrace the unpredictability of the trail. For the autonomous traveler ready to trade the museum queue for the mountain pass, the rewards are remarkable.
Via degli Dei: the path of the Gods
Among the long-distance routes originating in Florence, the Via degli Dei (path of the Gods) is undoubtedly the most celebrated. Connecting Bologna and Florence, this traverse of the Apennines is a journey through history as much as geography. The name derives from the mountains encountered along the route (Mount Adone, Monzuno and Mount Venere) echoing the pagan deities worshipped by ancient travelers.
Spanning approximately 80 miles (130 kilometers), the trek is typically completed in five to six days. The route is physically demanding, characterized by significant elevation gains as hikers ascend from the Po Valley, cross the Apennine ridge, and descend into the Arno Valley. The terrain is a mix of dense beech and chestnut forests, windswept ridges offering panoramic views, and gravel paths.
The true allure of the Via degli Dei lies in its historical underpinnings. Hikers frequently find themselves walking upon the Flaminia Militare, an ancient Roman military road dating back to 187 B.C. Sections of the original paving stones, or basolato, emerge from the forest floor, a tangible connection to the legions that once marched these same slopes. Unlike some of the more obscure Italian trails, the Via degli Dei is exceptionally well-marked and supported by a robust infrastructure of B&Bs, campgrounds, and agriturismi (farm stays), making it an approachable challenge for those new to multi-day trekking in Italy.
Cammino di Dante: walking through the Divine Comedy
For those seeking a journey that intertwines literature with landscape, “Il Cammino di Dante” offers a profound experience. This loop trek traces the likely path taken by the famous poet Dante Alighieri during his exile from Florence in the early 14th century. It is a route of solitude and contemplation, winding through the Casentino area and into Romagna, eventually reaching Ravenna where the poet is buried, before circling back.
The path is steeped in the atmosphere of the Divine Comedy. Hikers traverse the ancient Casentino Forests, a UNESCO World Heritage Site known for its towering silver firs and spiritual silence, evoking the “dark wood” of the Inferno. The itinerary connects medieval villages that have changed little since Dante’s time, including the walled town of Poppi with its imposing castle and the Romanesque Pieve di Romena.
This route is ideal for the traveler seeking cultural immersion and quietude rather than social hiking; accommodation often consists of mountain refuges (rifugi) and small, family-run inns.
The trail demands respect, with rugged ascents and sections that feel delightfully remote. It is a chance to see the Tuscany that exists in paintings: misty valleys, fortified towers on hilltops, and a timeless agrarian rhythm that persists despite the modern world.
The way of St. Francis: a pilgrimage to Rome
Heading south from the Basilica of Santa Croce in Florence, the Way of St. Francis (Via di Francesco) is a pilgrimage of epic proportions, leading eventually to St. Peter’s Basilica in Rome. While the full route to the Vatican takes several weeks, the northern leg from Florence to the sanctuary of La Verna is a popular standalone trek, or the beginning of the “Grand Tour” of walking pilgrimages.
This route is deeply spiritual and explicitly nature-focused. It moves away from the manicured vineyards of popular imagination and into the wilder, eastern edge of Tuscany. The goal of the first major section is the sanctuary of La Verna, perched high on a rocky precipice. It is here that St. Francis is said to have received the stigmata. The climb to the sanctuary through the monumental forest of the Casentino is a highlight of Italian trekking, offering a blend of physical exertion and mystical atmosphere.
Continuing past La Verna, the trail crosses into Umbria, the “green heart of Italy,” smoothing out into rolling valleys dotted with olive groves and art cities like Città di Castello and Gubbio. The landscape shifts dramatically from the rugged Tuscan Apennines to the softer, luminous light of the Umbrian hills. For those committed to the full pilgrimage, the arrival in Rome is significant, culminating in the walk down the via della Conciliazione toward the Vatican.
Completing such a long journey requires logistical planning for the return, as few hikers walk back the way they came. Fortunately, Italy’s rail infrastructure makes the transition from pilgrim to modern traveler seamless. At the end of the path, to come back to Florence pilgrims can catch the Italo high speed train, which covers the distance in roughly 90 minutes, offering a swift and comfortable counterpoint to the weeks spent on the trail.
Anello del Rinascimento: the Renaissance ring
The Anello del Rinascimento (Renaissance Ring) is a 170-kilometer circular route surrounding the city of Florence, designed to be hiked in sections or as a continuous loop over roughly a week.
The defining feature of this trek is the constant, shifting perspective of the Duomo. As you circumnavigate the city, the great red dome of the cathedral serves as a pivot point, visible from various angles and distances, grounding the hiker in the geography of the region. The trail meanders through the hills of Fiesole, the forests of Vallombrosa, and the olive groves of Impruneta, famous for its terracotta.
The terrain is a mix of dirt paths, forest trails, and country lanes. Because it remains relatively close to the urban center, the Anello del Rinascimento offers a unique blend of nature and architecture. Hikers encounter Medici villas, ancient monasteries, and castle ruins, all while maintaining a visual connection to the city below. It is an accessible option that requires less wilderness survival gear, but still demands sturdy legs and good navigation skills.
Via Romea del Chianti: trekking through wine country
For the epicurean hiker, the Via Romea del Chianti offers a sensory-rich alternative to the mountain routes. This path heads south from Florence through the heart of the Chianti Classico region, aiming toward Siena. It is a route defined by the classic Tuscan aesthetic: rolling hills covered in geometric rows of vineyards, avenues of cypress trees, and sun-baked farmhouses.
Historically this was a connector route used by pilgrims to join the Via Francigena, the major medieval artery to Rome; today it serves as a journey through one of the world’s premier wine regions. The walking is generally less strenuous than the Apennine crossings, characterized by the famous strade bianche (the white gravel roads that crisscross the countryside).
The itinerary passes through iconic towns such as San Casciano and Castellina in Chianti. The logistical advantage here is the abundance of high-quality agriturismi, allowing hikers to pair their daily exertion with wine tastings and farm-to-table dining. It is a trek that feeds the body as well as the soul, offering a deep dive into the agricultural heritage that shapes the Tuscan identity.
Practical logistics for the independent hiker
Embarking on a multi-day hike in Italy requires preparation that goes beyond booking a flight. The following logistics are helpful for a safe and enjoyable experience.
Timing is critical
The Italian summer (July and August) can be very hot, with temperatures in the valleys often exceeding 95°F (35°C). The best windows for trekking are spring (May – June) and autumn (September – October). These shoulder seasons offer mild temperatures and vibrant colors, though hikers should be prepared for occasional rain.
Gear essentials
While these are not technical mountaineering routes, the terrain is uneven and rocky. Low-cut sneakers are insufficient; lightweight, broken-in hiking boots with ankle support are mandatory. Trekking poles are highly recommended, particularly for the steep descents on the Via degli Dei and the Casentino routes. A high-capacity water bladder is also useful, as water sources can be infrequent on ridge lines.
Navigation
Signage in Italy has improved dramatically, with the red-and-white stripes of the CAI (Club Alpino Italiano) marking most trails. However, relying solely on physical signs is risky. Independent hikers should download GPX tracks to a smartphone or GPS device. Apps like Komoot, Mapy or Outdooractive are widely used and reliable for these specific regions.
Accommodations
On popular routes like the Via degli Dei, beds are limited. During peak season, it is necessary to book accommodations (whether hostels, B&Bs, or refuges) weeks, if not months, in advance. Many establishments along these pilgrimage routes offer a “credenziale” (pilgrim’s passport), which can be stamped at each stop and often grants access to discounted lodging.
