Hills & Riviera: The Grand Tuscan Journey
Itinerary
Embark on an unforgettable four-day cycling adventure through the heart of Tuscany. From medieval hill towns to Renaissance cities and the sun-drenched coast, this expertly designed journey blends world-class riding with rich cultural immersion.
Each day brings new landscapes and experiences, rolling countryside, iconic vineyards, and historic towns, all united by Tuscany’s timeless charm. Ride through picturesque valleys, explore centuries of history, and savor the region’s celebrated cuisine and hospitality.
Whether you're gliding past olive groves or coasting toward the sea, this journey is more than a cycling trip, it’s a deep dive into the spirit of Tuscany. Join us for four exhilarating days of discovery, beauty, and adventure.
Highlights
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Cycle Tuscany’s Iconic Landscapes – from Medieval Hill Towns to Coastal Elegance
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Ride into Renaissance Cities and Along Vineyard-Lined Country Roads
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Experience World-Class Cycling Enriched by History and Culture
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Savor Authentic Tuscan Cuisine and the Charm of Hidden Villages
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Finish at the Mediterranean Coast, Where Mountains Meet the Sea
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Discover Tuscany’s Spirit – Olive Groves, Rolling Hills, and Timeless Hospitality
Day 1 - Siena Warm Up
Begin your journey in the medieval heart of Siena, exploring its iconic Piazza del Campo and historic architecture on foot. From Porta Romana, the ride unfolds into the peaceful Sienese countryside, passing through Arbia and the storied hills of Montaperti, site of a legendary 13th-century battle. The day concludes with scenic climbs offering panoramic views back over Siena’s timeless skyline.
Hotel Athena
Level 2 - Easy
31Km
Activity
BikingDay 2 - Siena to Florence
Embark on a challenging and unforgettable ride from Siena to Florence, tracing a route steeped in history, culture, and iconic Tuscan beauty. Begin in the heart of Siena, then ride through the rolling hills of Chianti, passing historic villages like Radda and Panzano. Enjoy sweeping vineyard views, steep climbs, and rewarding descents as you make your way through Greve and Impruneta. The journey culminates with a dramatic entrance into Florence, ending at Piazzale Michelangelo and the majestic Cathedral of Santa Maria del Fiore, a breathtaking finish to a ride through centuries of art and legacy.
Torre dei Lari
Level 5 - Very challenging
93.4Km
Activity
Biking
Day 3 - Florence to Lucca
Leave the bustle of Florence behind as you follow riverside bike paths through Cascine Park and into the countryside. After a scenic climb through olive groves to Carmignano, enjoy a thrilling descent into Vinci, birthplace of Leonardo da Vinci. Refuel before continuing through the peaceful Lucchese hills and rural roads toward Altopascio. Your ride ends in the beautifully preserved city of Lucca, where Renaissance walls and cobbled streets mark the perfect close to a day rich in history, scenery, and cycling joy. In the evening, you’ll attend a live concert featuring the music of Giacomo Puccini, where his most beloved arias and compositions are performed and sung—a moving tribute to the great Tuscan composer in the city that inspired his timeless works.
Hotel Palazzo Dipinto
Level 5 - Very challenging
95.8Km
Activity
BikingDay 4 - Lucca to Viareggio
Your day starts with a spin along Lucca’s historic Renaissance walls, offering sweeping views of the quiet streets below. From there, follow the Serchio River toward Monte San Quirico into the lush Val Freddana, a local favorite for its smooth, scenic roads. After a gentle climb to Montemagno and a classic Tuscan coffee stop, descend toward the coast, passing through Camaiore and the artistic town of Pietrasanta. End your journey in style at Viareggio, a chic coastal resort where palm-lined promenades meet the Tyrrhenian Sea. A perfect finish to an unforgettable Tuscan adventure.
Hotel Residence Esplanade
Level 2 - Easy
40.8Km
Activity
Biking
Day 5 - Viareggio to Livorno
Leave the charm of Viareggio behind as you follow the coastal bike path, gliding past palm-lined promenades and Liberty-style buildings. After a gentle ride through Marina di Vecchiano and Migliarino Pisano, the scenery opens to pine forests and coastal plains. Cross the Serchio River and continue along the Aurelia, mindful of increasing traffic.
Soon Pisa greets you with its iconic skyline. Ride straight to the Leaning Tower and enjoy the vibrant student life in this historic square. Leaving the city, the route relaxes again along a smooth bike path toward Marina di Pisa, following the Tyrrhenian Sea to the coast.
The final kilometers bring you to Livorno, a historic port city rich in culture and Mediterranean spirit. A perfect day blending nature, history, and the open horizon, celebrating Tuscany one pedal stroke at a time.
Hotel Agave in Città
Level 2 - Easy
64 km
Activity
BikingDay 6 - Beyond the Ride: Rest, Reflect, Relish
Unwind by the sea as you trade pedals for peace. This final day is all about slowing down on the Tuscan coast: soaking in the sun, feeling the sea breeze, and savoring the memories of the roads you’ve ridden. It’s a chance to relax, share stories with fellow travelers, and reflect on the adventure that brought you here.
Level 1 - Very easy
Activity
Relax & Discover
Trip wows
This thoughtfully crafted journey offers the perfect balance of cycling, culture, and comfort, guiding you through Tuscany’s most scenic roads and storied towns. With every detail taken care of, you’re free to enjoy the landscapes, the flavors, and the quiet beauty that make this region unforgettable.
A Curated Journey Designed for Riders Who Love the Details
This isn’t just a pretty ride...it’s a perfectly tuned cycling escape. With top-notch bikes, turn-by-turn GPS routes, your luggage magically waiting at the next stop, and boutique stays full of character, all you have to do is pedal and soak it all in. And if you ever need a hand? Help is just a phone call away.
Savor the Flavors and Rhythm of Authentic Tuscany
From leisurely café stops in sleepy piazzas to farm-fresh meals in the heart of wine country, this trip is a celebration of Tuscan lifestyle. Enjoy one-of-a-kind moments like a live Puccini concert in Lucca, and meals that highlight the region’s proud culinary traditions.
Ride Through Centuries of Art, Culture, and Storytelling
Follow a route where every pedal stroke passes through living history. From the Renaissance grandeur of Florence to walled cities and rustic hamlets, you’ll trace the footsteps of artists, inventors, and winemakers who shaped Tuscany’s legacy.
Ride from Medieval Hill Towns to the Sparkling Sea
Begin your journey in Siena’s enchanting historic center, where medieval architecture and cobbled streets set the tone. Ride through ever-changing terrain—vineyard-covered hills, tranquil valleys, and artistic towns...culminating on the chic Mediterranean coast of Forte dei Marmi, where the Apuan Alps meet the sea.
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hotels
Please note that accommodations may vary based on availability.
Hotel Athena
A charming 4-star hotel nestled within the historic walls of Siena, just a short walk from the iconic Piazza del Campo. Offering panoramic views of the Tuscan countryside, the hotel combines modern comfort with traditional Tuscan hospitality. Guests can enjoy elegantly furnished rooms, a rooftop terrace, and a renowned restaurant serving local cuisine. Hotel Athena provides a welcoming base for exploring the heart of Tuscany.
Hotel level
Quality
Plus
Restaurant, Parking
Torre dei Lari
Torre dei Lari Residenza d’Epoca is a historic villa nestled in the peaceful hills near Florence, offering a perfect retreat for cycling enthusiasts. Guests can relax in elegantly furnished rooms, enjoy the outdoor pool and garden, and recharge before exploring the scenic Tuscan countryside by bike.
Hotel level
Premium
Plus
Pool, Restaurant, Parking
Hotel Palazzo Dipinto
Situato nel centro storico di Lucca, a 650 metri da Piazza Anfiteatro, il Palazzo Dipinto offre camere spaziose con WiFi gratuito e un bar interno. Le sistemazioni dispongono di un bagno privato e una TV a schermo piatto, e alcune vantano un'area salotto. Il Palazzo Dipinto dista 150 metri dalla Basilica di San Frediano e 10 minuti di cammino dalla Cattedrale di Lucca.
Hotel level
Premium
Plus
Parking, Free WiFi, Bar
Hotel Residence Esplanade
The Hotel Residence Esplanade is an elegant Liberty-style hotel located just 50 meters from the beach, next to the Pineta di Ponente in the heart of Viareggio. It offers stylish rooms and modern apartments with free Wi-Fi and excellent comfort, along with an Italian restaurant, a private wellness spa, and a fully equipped fitness area, ideal for a relaxing yet active stay.
Hotel level
Premium
Plus
SPA, Restaurant, Gym
Hotel Agave in Città
Agave in Città is an elegant hotel in the heart of Livorno, set in a historic building. It offers modern, comfortable rooms, an infinity pool, spa, and fitness center, just a short walk from the port and the city’s main attractions.
Hotel level
Quality
Plus
Pool, Parking, GymImportant info
- 5 nights accommodation in charming hotels or guesthouses (double occupancy)
- 5 breakfasts, 1 light lunch and 1 dinner featuring local cuisine
- Living Roads Kit: cycling cap and water bottle
- Helmet, Pedals and all necessary chargers and pump
- Detailed GPS routes
- Daily luggage transfer between accommodations
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- E-bike or premium road bike rental included for the entire tour (feel free to bring your own bike if you prefer)
- Ticket/s (one per person) for Puccini Concert Live Show in Lucca
- Private guide for the entire duration of the tour
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Transfer on Day 1/Day 5 from/to the nearest train station/airport
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
Included
- 5 nights accommodation in charming hotels or guesthouses (double occupancy)
- 5 breakfasts, 1 light lunch and 1 dinner featuring local cuisine
- Living Roads Kit: cycling cap and water bottle
- Helmet, Pedals and all necessary chargers and pump
- Detailed GPS routes
- Daily luggage transfer between accommodations
- Welcome briefing and orientation by a local representative
- Emergency phone support during the tour
- Secure bike storage at each overnight location
- Access to the Ride with GPS navigation app
- E-bike or premium road bike rental included for the entire tour (feel free to bring your own bike if you prefer)
- Ticket/s (one per person) for Puccini Concert Live Show in Lucca
Not included
- Private guide for the entire duration of the tour
- Single room supplement
- E-Bikes supplement
- Additional gears
- Travel insurance (highly recommended). See our protection plan here.
- Airfare or transportation to/from the tour start and end locations
- Transfer on Day 1/Day 5 from/to the nearest train station/airport
- Lunches and dinners not specified in the inclusions
- Personal expenses (e.g., souvenirs, drinks, snacks)
- Optional activities or excursions not mentioned in the itinerary
- Gratuities for drivers or hotel staff
- Additional nights of accommodation before or after the tour dates
You’ll receive detailed GPS routes, accommodation info, and remote support. Follow the route at your own pace, with full independence but peace of mind.
Our tours range from easy to moderate and are suitable for a wide range of fitness levels. You don’t need to be an athlete, whether you’re a beginner or a more experienced cyclist or hiker, we have options tailored to your ability and pace. E-bike rentals are also available for extra comfort on selected routes. Not sure which adventure suits you best? Check out our Activity Levels to find your perfect fit.
Our tours, both Self-Guided and Full Supported, are ideal for solo travelers.If you choose a Self-Guided experience, you’ll enjoy the freedom of independent travel with the reassurance of our reliable remote support whenever you need it.
Prefer a Full Supported tour? You’ll join a welcoming group of like-minded travelers and be accompanied by expert local guides ready to assist you throughout the journey. Whether you’re riding, hiking, or sharing a meal, you’ll always find connection and shared moments.Traveling solo doesn’t mean being alone, it means choosing your own pace while being part of something meaningful.
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Get in touch with us
Where would you like to go?
Why Living Roads?
OUR LOCAL TOUCH
As locals, we create journeys inspired by the way we live. Enjoy the best of Italian Roads and Hospitality with our expertise of more than 50 years as a tour operator.
FOR EVERYONE
Our tours are open to everyone, with different levels of difficulty. They’re never meant to be a race, but rather a chance to embrace the slow joy of discovery.
Culture you can taste
Cycling means earning every view and every bite. Our tours include regional wine tastings, cooking class, countryside dinners, and food experiences you’ll remember forever.
CURATED ACCOMODATIONS
Our selection of hotels is guided by the desire to promote local businesses and historic palaces or buildings, creating the perfect blend of authenticity and charm.
ASSISTANCE
You’ll never be alone on the road. You can always count on our remote support during the Self-Guided tours, or on the expertise of our local guides during the guided or joinable tours.
Meaningful miles
We ride slow and smart: our tours are designed to support local communities and reduce environmental impact for a way of traveling that feels as good as it looks.