Lucca & Siena Bike Tour

  • 8 days/7 nights
  • Tour Type: multi-destination
  • Level: 3/5
  • Price From €3.990

Lucca & Siena Bike Tour

  • 8 days/7 nights
  • Tour Type: multi-destination
  • Level: 3/5
  • Price From €3.990

Lucca & Siena Bike Tour Overview

Embark on an unforgettable eight-day cycling adventure, immersing yourself in the captivating landscapes surrounding two of Tuscany’s most beautiful cities, Lucca and Siena. In the initial three days, pedal through the undulating hills near Lucca, where olive groves, vineyards, majestic oak woodlands, rows of towering Cypress trees, and untamed forests create a picturesque backdrop. Leaving Lucca behind, our journey takes us towards San Gimignano, often referred to as the “Manhattan of the Middle Ages,” and then onwards to Siena, tracing the historic Via Francigena. Siena, our tour’s final destination, awaits with its incredible terrain and the allure of splendid gravel roads. Throughout this cycling odyssey, indulge in delightful gastronomic experiences, savouring exquisite cuisine and exceptional wines at our handpicked trattorias. Our local, bilingual expert guides will unravel the secrets of Italy’s hidden artistic gems, ensuring an enriching cultural experience alongside the thrill of the ride.

Bike Tour Itinerary

Upon your arrival at Pisa International Airport, our dedicated staff will extend a warm greeting and seamlessly escort you to your charming accommodation nestled in Lucca. Following a light lunch, we’ll embark on a bike tune-up session and our inaugural warm-up ride, affectionately known as “sgambatella” in Italian parlance. This delightful ride aims to invigorate your legs, preparing them for the exciting days that lie ahead. Venturing from downtown Lucca, our route swiftly leads us to the mesmerizing hills adorned with ancient olive groves and vineyards. An evening aperitivo at one of the region’s finest enotecas sets the stage for a delightful toast, heralding the incredible week awaiting us. Returning to the hotel, we’ll prepare for an enchanting dinner at one of Lucca’s premier restaurants, creating a perfect start to your Tuscan adventure.

Meals: Dinner

Cycling: distance 35 km, elevation 400 meters

Pick-up location: Pisa International Airport

Fueling up with a sumptuous Italian breakfast, we eagerly anticipate the day’s cycling adventure. Our experienced guides will lead you through picturesque landscapes, setting the stage for the ascent towards the majestic Monte Serra. Prepare for a notable climb, spanning approximately 8 kilometres with a manageable average gradient of 6%. We approach this challenge with precision, ensuring an enjoyable pace that allows you to relish the stunning vistas unfolding along the route. Upon conquering Monte Serra, a pause at the summit awaits, providing an ideal opportunity for capturing memories with photos and savouring the breathtaking panorama of Pisa, including its iconic leaning tower. Our descent guides us through the charming locales of Calci and Nozzano Castello, treating you to the allure of the Tuscan countryside. Continuing our pedal-powered journey for another 20 kilometres, we face the final gentle ascent before heading back to Lucca, a 3.5-kilometre climb leading to the enchanting Pieve S. Stefano, nestled amidst ancient olive groves. With the evening at your leisure, take the opportunity to explore the city’s attractions or simply unwind before a delightful dinner awaits.

Meals: Breakfast, Dinner

Cycling: distance 90 km, elevation 800 meters

As the sun graces us with a new day, we embark on another cycling journey after savouring a nourishing breakfast. Our route takes us along serene roads, winding through lush forests and picturesque valleys, culminating in the historic village of Fiano. From this vantage point, a breathtaking view of the sea awaits, offering a moment of tranquillity and appreciation. A gradual ascent follows, leading us to Passo Sella, situated in the heart of the remarkable national park of the Apuan Alps. Here, amidst the natural splendour, we pause for a well-deserved lunch in San Rocco, a charming Medieval hamlet. Indulge in a homemade feast that captures the essence of local flavours, preparing you for the adventures that lie ahead. Our cycling odyssey continues with a thrilling descent, navigating through gentle ascents and smooth descents affectionately known as “Mangia e bevi” in Italian slang. Passing through the enchanting Turrite Cava, we follow the course of the Serchio River, captivated by the sight of Ponte del Diavolo. Upon returning to our hotel, take a moment to unwind and rejuvenate before meeting up for a memorable dinner, perfectly capping off another day of exploration.

Meals: Breakfast, Dinner

Cycling: distance 90 km, elevation 800 meters

As the sun graces our cycling haven, we embark on a captivating journey towards our next destination, the medieval jewel of San Gimignano. The morning ride unfolds with a delightful stretch, presenting a terrain of gentle undulations after we depart from Lucca. Our path leads us through landscapes that harmonize with the rhythms of Tuscany, where the initial flat terrain gradually transitions into subtle slopes. Our route unveils the picturesque town of San Miniato, renowned for its exquisite wine and the coveted white truffles that grace its soil. A well-deserved pause for lunch invites us to indulge in the region’s culinary treasures, savouring local wines that bear the essence of the Tuscan terroir. The flavorful white truffles, a hallmark of San Miniato’s gastronomic legacy, heighten our dining experience. Post-lunch, our cycling odyssey continues as we embrace the Via Francigena, a historic route that guides us through the enchanting Val D’Elsa. This scenic path paves the way to our final destination, San Gimignano, where the medieval allure awaits. Marvel at the architectural splendour of La Rocca di Montestaffoli and the iconic Torre Grossa as we delve into the town’s rich history. With the day’s ride behind us, take a moment to relax amidst the timeless charm of San Gimignano. As evening descends, prepare to immerse yourself in the ambience of a traditional dinner, the perfect culmination of another day of exploration and discovery.

Meals: Breakfast, Dinner

Cycling: distance 80 km, elevation 1400 meters

Expedition As the sun ascends over the medieval charm of San Gimignano, we embark on another day of cycling splendour towards the iconic city of Siena. Following a delectable breakfast that fuels our spirits, we set forth on a journey marked by undulating landscapes and captivating vistas. The day’s route unfolds with a gentle ascent, guiding us toward Colle Val d’Elsa and the historic village of Strove, its foundations echoing tales from the 6th century. A brief pause allows us to rejuvenate, preparing for the scenic stretch along the renowned Via Francigena. Traversing this ancient pilgrimage route, we encounter the enchanting hamlet of Monteriggioni, steeped in historical allure. Here, amid its medieval charm, we pause for a light lunch, indulging in local flavours that define the Tuscan culinary experience. Our journey continues along the Cassia, leading us toward the illustrious city of Siena. As the afternoon unfolds, we find moments of respite to explore and unwind in the embrace of Siena’s cultural richness. Immerse yourself in the city’s unique ambience, strolling through its historic streets and discovering its timeless beauty. As the day draws to a close, anticipate a memorable evening ahead, filled with the promise of discovering Siena’s culinary delights before the night unfolds its magical embrace.

Meals: Breakfast, Dinner

Cycling: distance 70 km, elevation 1300 meters

Fueling up with a hearty breakfast, we embark on the Etruscan ride, a cycling escapade toward the beautiful Montagnola Senese. Our journey unfolds along tranquil roads adorned with verdant foliage, offering a serene backdrop for today’s adventure. En route, we traverse historical landmarks, including the medieval gem of Monteriggioni, a fortified hamlet encircled by its ancient defensive walls, and Sovicille. Delve into the rich tapestry of this region, where echoes of the Etruscan civilization linger, whispering tales of an era predating the Romans. As we pedal through the landscapes that once hosted the Etruscan populace, immerse yourself in the palpable history that permeates the air. The return journey presents a panoramic vista, offering one of the finest views of Siena and its iconic skyline—a moment to savour and capture. Back at our haven, take a well-deserved respite, embracing the tranquillity before we reconvene for a delightful dinner. In the twilight hours, allow the day’s experiences to settle as you relish the anticipation of another day in the heart of Tuscany.

Meals: Breakfast, Dinner

Cycling: distance 70 km, elevation 850 meters

Today unfolds as we set our course eastward, tracing the border of the Chianti region on our way to the Val di Chiana, renowned for its majestic Chianina cow breed. Our meticulously crafted route navigates the very paths embraced by the iconic L’Eroica event, immersing you in the charm of the Chianti landscape and the breathtaking Crete Senesi, famed for its distinctive clay hills. Embarking from Arbia and Asciano, we venture toward Castelnuovo Berardenga, a picturesque pause for a light lunch amid the captivating surroundings. As we journey back, both groups will traverse a gentle gravel section—a firsthand encounter with the very roads that have etched the Strade Bianche Pro Race into cycling lore. Today’s ride is a tapestry of scenic beauty and cultural richness, offering an immersive exploration of the storied landscapes that define this region. This evening, as the sun sets on your Crete Senesi adventure, relish the camaraderie forged on these winding roads and anticipate the final leg of our Tuscan cycling odyssey.

Meals: Breakfast, Dinner

Cycling: distance 85 km, elevation 1500 meters

As the sun rises on our final morning, we gather for a poignant farewell over freshly brewed espresso. Together, we reflect on the unforgettable chapters of our Tuscan cycling journey, each pedal stroke etching stories of scenic hills, charming villages, and the shared passion for the open road. At this moment, amidst the aroma of rich coffee and the echoes of our cycling exploits, we celebrate more than a week of adventure. We celebrate the bonds of camaraderie forged on winding paths, the laughter shared under the Tuscan sun, and the enduring friendships woven through the love of this incredible sport. As we bid arrivederci, carrying with us the cherished memories of our cycling escapade, we take pride in the lasting connections made on these picturesque roads. Until our paths cross again, may your cycling adventures continue, and the spirit of Tuscany accompany you on every ride. Grazie mille for being part of this remarkable journey.

Meals: Breakfast

Drop-off: Florence or Pisa International Airport

What’s included and Details

Upcoming Tours

Mar 16 – Mar 22, 2025

From € 3.990

May 17 – May 17, 2025

From € 3.990

Jun 22 – Jun 28, 2025

From € 3.990

Sep 28 – Oct 04, 2025

From € 3.990

Go Private or Customize your bike tour

Tour Guides

Gabriele Mirra

Founder and Professional Guide

Max Pullinger

Chief Customer Engagement and Partner

Omar Marouan

Professional Guide

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