Born from These Roads
Living Roads was born from the footsteps of those who’ve walked, cycled, and loved this region for generations. Our itineraries aren’t just routes, they’re memories. Designed by locals, each tour opens secret doors to villages, stories, and flavors only we know.
Planning Less Living More
1. Book your free call
Let’s talk. Schedule a call with one of our trip designers to understand your style, preferences, and goals.
2. Get your proposal
We’ll match you with the perfect itinerary self-guided or full supported and send you all the details, from routes and services to available dates and lodging.
3. Confirm & ride
Lock in your spot and you’re ready to ride. All that’s left is to enjoy the journey, we’ll handle the rest.
What every Living Roads journey is made of
What’s included?
Start when you want, choose your dates and ride at your pace
DIGITAL TRAVEL GUIDE
with curated info (lunch spots, hotel recs, dinner options, POIs) via RWGPS
VERIFIED GPS + GRP ACCESS
via RWGPS for a smooth, no-surprises journey
PRE-DEPARTURE VIDEO CALL
with a local expert to help you prep
EMERGENCY PHONE SUPPORT
during the tour
CAREFULLY SELECTED LOCAL ACCOMODATIONS
WELCOME PACK:
Jersey + branded bottle
ALL BREAKFAST AND SELECTED MEALS (lunches and dinners) included
ROAD BIKE INCLUDED
CURATED EXPERIENCES
including wine tastings, guided tours, and cultural activities (varies by tour)
LUGGAGE TRANSFERS BETWEEN ACCOMODATIONS
SECURE BIKE STORAGE
EXTRA:
(Available for an additional cost)
Arrival & departure transfers
Private guide for personalized support from an expert local guide
E-bike or gravel bike rental
5 days (4 nights)
200 km
Intermediate
January - December 2026
Tuscan Treasures: A Cycling Journey from Florence to Siena
A journey by bike through Renaissance art, wine roads, and lunar landscapes of Tuscany
Starting from:
€ 1.770,00 /person
5 days (4 nights)
200 km
Intermediate
January - December 2026
Renaissance Ride: from Siena to the Heart of Florence
A cycling journey through Chianti, medieval villages, and Renaissance wonders
Starting from:
€ 2.050,00 /person
5 days (4 nights)
210 km
Intermediate
January - December 2026
Three Heroic Days: Where History Meets Gravel
A vintage-inspired adventure through Chianti, Siena, Montalcino, and the soul of Tuscany
Starting from:
€ 1.790,00 /person
5 days (4 nights)
262 km
Intermediate
January - December 2026
Hills & Riviera: The Grand Tuscan Journey
A cycling journey through Chianti, medieval towns, and Renaissance beauty
Starting from:
€ 1.990,00 /person
9 days (8 nights)
560 km
Challenging
January - December 2026
Tuscan Gravel Legends: The Most Epic Routes Become One
An 8-day heroic cycling journey through vineyards, villages, volcanoes and the sea
Starting from:
€ 2.990,00 /person
5 days (4 nights)
270 km
Intermediate
January - December 2026
Umbria to Tuscany: Bartali’s Legendary Route
A self-guided cycling adventure from Umbria to Tuscany, across ancient towns, lakeside paths, and Chianti vineyards
Starting from:
€ 2.490,00 /person
What’s included?
Set dates for a multiday group tour with full support
DIGITAL GUIDE + GPS ACCESS via RWGPS
EXPERT LOCAL GUIDE
with you every day
24/7 SUPPORT TEAM
+ pre-trip video consultation
SUPPORT VAN
throughout the tour for luggage & rider assist
CAREFULLY SELECTED ACCOMODATIONS
WELCOME PACK:
Jersey, bottle, and cap
ALL MEALS INCLUDED (snacks, drinks, lunches & dinners)
ROAD BIKE
CURATED EXPERIENCES
including wine tastings, guided tours, and cultural activities (varies by tour)
INSURANCE COVERAGE for peace of mind
LUGGAGE TRANSFERS BETWEEN STOPS
SECURE BIKE STORAGE
EXTRA:
(Available for an additional cost)
Arrival & departure transfers
E-bike or gravel bike rental
6 days (5 nights)
170 km
Intermediate
May 10 - May 17 + Oct 25 - Oct 31
Lost Roads of Sicily: Baroque to Arab Splendor
A journey by bike through ancient civilizations, baroque cities, and volcanic landscapes of Sicily
Starting from:
€ 3.950,00 /person
7 days (6 nights)
790 km
Intermediate
May 24 - May 31 + Oct 11 - Oct 18
Two Seas Trail: Crossing Italy’s Hidden Gems
An epic coast-to-coast odyssey through Italy’s secret soul
Starting from:
€ 4.790,00 /person
Ready to ride the real Italy?
Tell us how you love to travel — we'll help you find the cycling tour that fits your pace, your style, your dream.
Choose your ride:
Let’s start planning your ride
Born from the land, shared from the heart
Our founder’s story isn’t about building a business — it’s about inviting you home, one ride at a time.
Every journey starts with a question
Curious about the ride, the roads, or what to pack? We’ve got you covered, here’s everything you need to know before you go
Who can join your tours?
Anyone! Our tours range from easy to moderate and suit beginners to seasoned riders. E-bikes are available for extra comfort or mixed-ability groups.
Do I need to be in great shape?
No, you just need curiosity and the desire to explore. This isn’t a race.
Can I travel solo?
Absolutely. Many of our guests are solo travelers, we’ll tailor the journey for you.
How far in advance should I book?
We recommend 1–2 months ahead, especially during high season. But feel free to ask, we’ll do our best to accommodate.
Are airport/train transfers included?
Yes, when specified. We’ll confirm all details during your booking.
Can I cancel or change my trip?
Yes, with notice. Contact us or check our full terms.
What languages are available?
Tours are delivered in English. Italian materials are available upon request.