Self-Guided Hiking & Cycling Tours in Tuscany
Walk or ride through medieval villages, rolling vineyards and ancient pilgrim roads — at your own pace, with expert support every step of the way.
⭐ Read our 5 stars guest reviews on Google • 5 years in business • Service fee from 19% only
Why Choose Out of the Box Florence?
Out of the Box Florence is a Florentine adventure and local travel company founded in 2020 and dedicated entirely to slow, immersive travel across Tuscany, Umbria and Cinque terre. In five years we have helped more than 10,000 guests experience Italy on foot or in the saddle or with our super Minivans for private and customised tours — from solo adventurers to families, from complete beginners to seasoned athletes.
Whether you dream of following a medieval pilgrim road through ancient forests, tackling the legendary white gravel roads of Chianti, or simply cycling village to village with a glass of Brunello waiting at the end of the day — we design the journey around you.
🏅 Our promise to every guest:
Premium GPX tracks tested by our own team · Hotel reservations matched to your budget · Daily luggage transfers so you travel light · Wine tastings & cooking classes bookable along every route · Lowest service fee on the market: just 19% of total trip cost
🥾 Self-Guided Hiking Tours
There is no better way to understand Tuscany and Umbria than on foot. Our curated hiking routes follow centuries-old paths — pilgrim roads, Roman consular ways, Apennine ridges — away from tourist buses and crowds. Each trail is mapped with our premium GPX tracks, downloadable to any device before departure, so you always know exactly where you are.
🌲 Via degli Dei — Bologna to Florence (130 km · 5–7 days)
One of the most iconic long-distance walks in Italy, the Via degli Dei (“Road of the Gods”) crosses the Northern Apennines between Bologna and Florence, passing through ancient chestnut forests, medieval hamlets and Etruscan hilltops named after Roman deities: Monte Venere, Monte Adone, Monte Luario.
📏 Distance: ~130 km
⏱️ Recommended duration: 5 to 7 days
📈 Elevation gain: ~4,500 m cumulative
🏨 Stage villages: Marzabotto · Monzuno · Madonna dei Fornelli · San Piero a Sieve · Fiesole · Florence
🌿 Best seasons: April to October
We arrange accommodation at every stage town — from agriturismo with home-cooked dinners to boutique hotels — adjusted to your budget. Our luggage transfer service collects your bag each morning from the hotel and delivers it to your next stop before you arrive, so you hike with only a day pack.
🏛️ Florence to Pisa — The Arno Valley Route (~100 km · 4–5 days)
Follow the Arno river westward through wine estates, olive groves and Renaissance towns. This gentle, mostly flat trail is ideal for first-time long-distance hikers and families. Highlights include the medieval walled town of Empoli, the thermal baths of Monsummano Terme and the breathtaking Piazza dei Miracoli in Pisa — a reward well worth every step.
📏 Distance: ~100 km
⏱️ Recommended duration: 4 to 5 days
📈 Difficulty: Easy to Moderate
🏨 Stage towns: Signa · Empoli · San Miniato · Fucecchio · Santa Croce sull’Arno · Pisa
🏙️ Florence to Siena — Via Romea del Chianti (~80 km · 4–5 days)
Walk through the heart of Chianti on ancient mule tracks connecting hilltop castles, wine estates and Romanesque parish churches (pievi). The route descends into Siena’s extraordinary medieval centre — a UNESCO World Heritage Site — for a finish you will never forget.
📏 Distance: ~80 km
⏱️ Recommended duration: 4 to 5 days
🍷 Highlights: San Casciano in Val di Pesa · Badia a Passignano · Castellina in chianti · Siena
Siena to Assisi — Mix pf paths (~200 km · 10–12 days)
This is the grande dame of Italian pilgrim routes: a section of the ancient pilgrims roads that threads through the Crete Senesi, Cortona, Perugia and the green hills of Umbria to reach the Basilica of Saint Francis in Assisi. The landscape shifts from Tuscan cypress-lined ridges to Umbrian valleys of extraordinary stillness.
📏 Distance: ~200 km
⏱️ Recommended duration: 10 to 12 days
📈 Difficulty: Moderate to Challenging
🌄 Key stages: Siena · Cortona · Bastia Umbra · Perugia · Assisi
🌿 Best seasons: March to November
Our team has walked every kilometre of this route personally. We provide stage-by-stage waypoint notes, emergency contacts, and 24/7 WhatsApp support throughout your journey.
💡 Guided hiking also available
Prefer not to go alone? All hiking routes are available as fully guided departures with our expert local guides — historians, naturalists and passionate walkers who bring the landscape to life. Ask us for availability.
🚴 Self-Guided Gravel Cycling Tours
Out of the Box Florence is the leading specialist in gravel cycling holidays in Tuscany, Central Italy and Cinque Terre. We design routes for every fitness level — from relaxed e-bike explorers to ambitious cyclists chasing epic climbs. All itineraries are built around our premium GPX tracks, tested by our team on every road surface, and updated seasonally.
Gravel cycling in Tuscany means white roads (strade bianche), vineyards and silence. It means cresting a hill at golden hour with a panorama of Val d’Orcia below you. It means earning your Chianti Classico.
🏆 Strade Bianche & L’Eroica Classic (2–5 days)
These are the white gravel roads that made Tuscany famous in the cycling world. The Strade Bianche WorldTour race and the legendary L’Eroica vintage cycling event both pass through this countryside — and we will put you on the same roads. Expect chalky white gravel, rolling Chianti hills, isolated farmhouses and postcard finishes in Siena’s Piazza del Campo.
📏 Loop options: 60 km, 120 km or multi-day
🚵 Surface: 60–70% gravel (strade bianche), 30–40% tarmac
🏆 Iconic segments: Montalcino sector · Asciano moonscape · Gaiole in Chianti · Siena finish
🍷 Florence to Siena — Chianti by Gravel (~90 km · 1-2 days)
The classic Tuscany cycling journey. Leave the Arno behind, climb into the Chianti hills and descend to Siena on a mix of gravel paths and quiet country lanes. We arrange wine estate tastings at Greve in Chianti and Radda to break up the stages beautifully.
📏 Distance: ~90 km
⏱️ Duration: 1 to 2 days cycling
📈 Difficulty: Moderate (suitable for regular cyclists)
🌆 Around Florence — Chianti Loops & Fiesole Hills (1–3 days)
Perfect as a warm-up, a standalone short break, or a starting experience for beginners. We craft custom loops departing directly from Florence — through Fiesole, the Mugello valley, the Chianti countryside — so guests can explore Tuscany without needing a transfer to a starting point.
📏 Distance: 30 to 90 km per day depending on loop
🚴 Ideal for: beginners, families, e-bike riders, city visitors wanting a cycling day
🌾 Val d’Orcia Gravel Explorer (3–5 days)
UNESCO-listed Val d’Orcia is the most photographed landscape in Italy — and the most spectacular on two wheels. Cypress-lined roads, thermal baths at Bagno Vignoni, the fortress town of Montalcino (home of Brunello wine), and the medieval gem of Pienza. We combine the best gravel sectors with the region’s unmissable cultural highlights.
📏 Distance: 150–200 km total
🌄 Highlights: Montalcino · Pienza · Bagno Vignoni · San Quirico d’Orcia · Castiglione d’Orcia · Monticchiello
🍷 Wine: Brunello di Montalcino tastings included on request.
🏛️ Gravel Around the White Roads of Pisa (2–5 days)
Beyond the Leaning Tower lies a landscape few tourists ever see: the rolling Pisan Hills (Colline Pisane), the thermal springs of Casciana Terme, ancient Etruscan roads and the wild Maremma coast. This route follows the same gravel tracks used in local amateur granfondo events and offers solitude, scenery and superb food.
📏 Distance: 80–150 km per day depending on route variant
🌊 Option: Extend to the Tyrrhenian coast for a beach finish
🏛️ Florence to Assisi — The Pilgrim’s Ride (~280 km · 3–5 days)
A route of extraordinary beauty and spiritual resonance, connecting two of Italy’s most beloved cities through Chianti, Val di Chiana, Lago Trasimeno and the green hills of Umbria. The road to Assisi passes through landscapes that have inspired painters and pilgrims for centuries. We provide detailed GPX navigation and accommodation at every stage.
📏 Distance: ~280 km
⏱️ Duration: 3 to 5 days cycling
📈 Difficulty: Moderate to Challenging
🏨 Stage towns: Florence · Chianti classico · Siena · Cortona · Montepulciano · Lago Trasimeno · Assisi
🏛️ Florence to Rome — La Grande Via (~450 km · 5–7 days)
The ultimate Italian cycling adventure: Florence to the Eternal City. Follow the Via Cassia corridor through Chianti, the Val d’Orcia, the volcanic Lazio hills and the Via Appia Antica into Rome. An epic journey that ends at St. Peter’s Square — a finish that will stay with you for life.
📏 Distance: ~450 km
⏱️ Duration: 5 to 7 days cycling
📈 Difficulty: Challenging (also available as e-bike tour)
🏨 Key stops: Siena · Montalcino · Bagno Vignoni · Sutri · Viterbo · Rome
💡 Guided cycling also available
All cycling routes can be ridden with one of our expert guides — local cyclists who know every road, every shortcut and the best café stop in every village. Guided departures include mechanical support, a dedicated support vehicle and a fully curated daily programme.
✅ What Every Tour Includes
Whether you book a self-guided or guided itinerary, every Out of the Box Florence tour comes with the same core service package:
Premium GPS Tracks — Every route is delivered as a tested, ready-to-use GPX file compatible with Garmin, Wahoo, Komoot, Wikiloc, Apple Maps and Google Maps. Our tracks include waypoints for accommodation, water stops, cafés, bike shops and points of interest. Our clients never get lost.
Daily Luggage Transfers — We collect your luggage every morning and deliver it to your next accommodation before you arrive. Travel with a light day pack and arrive relaxed. This service is included on all multi-day itineraries.
Hotel & Accommodation Booking — We handle all reservations. Tell us your budget — budget agriturismi, mid-range B&Bs, charming boutique hotels or luxury wine estates — and we match every stage to your preference. We work with trusted, independently selected partners across the entire route.
24/7 WhatsApp Support — Our team is reachable throughout your trip for navigation questions, emergency assistance or simple restaurant recommendations. Real humans, real-time responses.
Wine Tasting & Cooking Classes — We can organise authentic local experiences along any route: Chianti Classico estate tours, Brunello wine tastings, hands-on pasta and bread-making classes, truffle hunting in Umbria and olive oil mill visits. These are pre-bookable at the planning stage or added during your trip.
Bike Rental (cycling tours) — Quality gravel bikes and e-bikes available through our trusted partners in Florence. Helmet, repair kit, pump and panniers included. Bike fit consultation before departure.
💶 Transparent Pricing — The Lowest Service Fee on the Market
We believe adventure travel should be accessible. Out of the Box Florence charges a service fee of just 19% on the total trip cost — covering full itinerary planning, GPX tracks, luggage logistics coordination, accommodation booking and 24/7 support. This is among the lowest fees charged by any comparable operator in Italy.
There are no hidden charges. You pay the accommodation and experiences at the actual market rate; we simply add our transparent 19% for the planning and coordination work. For a 7-day cycling holiday, that typically amounts to a fraction of what a package tour operator would charge.
💰 Example: Florence to Rome Cycling (7 days)
Accommodation + meals + experiences: ~€1,200 per person
Out of the Box Florence service fee (19%): ~€228 per person
Total per person: ~€1,428 — fully supported, GPX-guided, luggage-transferred
(Prices are indicative and vary by season, hotel category and group size)
🌟 5 Years, 10,000 Happy Guests
Since our founding in Florence in 2020, Out of the Box Florence has grown entirely through word of mouth and the reviews of satisfied guests. We have never relied on mass-market booking platforms — our reputation is built one itinerary at a time.
Over 10,000 guests from 40+ countries have travelled with us
5 consecutive years of 5-star average ratings on Google
Routes personally scouted and updated each season by our team
Strong partnerships with local hotels, wineries and experience providers
Carbon-conscious travel: we prioritise accommodation on route to minimise transfers
📖 Read what our guests say: Out of the Box Florence — Google Reviews
📩 Plan Your Trip — Contact Us
Ready to start planning? Tell us your travel dates, preferred route, fitness level and budget — we will design a personalised itinerary and send you a detailed quote within 24 hours.
🌐 Website: www.outoftheboxflorence.com
✉️ Contact form: outoftheboxflorence.com/contact-us
💬 WhatsApp: +39 347 080 9904 (fastest response)
⭐ Google Reviews: See what our guests say
© Out of the Box Florence · Florence, Italy · Self-Guided & Guided Hiking and Cycling Tours · Tuscany · Umbria · Italy
