Grand Tour Italia

Grand Tour Italia

Rome to Florence

£3,200

Start Point

Orvieto
(Rome Fiumicino Airport)

Finish Point

Florence
(Florence Airport)

Support Team

Fully Supported + Feed Stations

Stages

5 Fully Guided

Longest Stage

Stage 4: 110km

Biggest Climb Stage

Stage 2: 1,900m+

Average Pace

14-19mph | 22-30kph

Peloton Size: 15

The Grand Tour Italia: Rome to Florence – a captivating 5 stage adventure unveiling the rich tapestry of Umbria and Tuscany.

This tour is more than just cycling; it is an opportunity to immerse yourself in a celebration of Italy’s rich heritage, breathtaking scenery, and cultural marvels.

Our inspiration for creating the Grand Tour Italia originates from our deep-rooted affection for these regions, nurtured by our family legacy and countless treasured memories.

Travel through Italy on the best cycling roads in Umbria and Tuscany, taking you on a journey through culturally significant towns of Assisi, Siena and San Gimignano. As you ride, you will be immersed in rich history and culture, discovering hidden gems like Citta della Pieve, Todi and Bevagna, each with its own unique blend of architecture and heritage.

Discover the heart of Chianti, known for its picturesque landscapes, world-class wines, and traditional Tuscan life. The tour culminates near Florence and the birthplace of the fabled Gino Bartali, a cycling legend and true hero of history.

The Grand Tour Italia promises an experience that will forever transform your perspective on cycling, blending historical richness and tradition with breathtaking scenery.

Get ready to embark on an adventure where every pedal stroke is an opportunity to connect with the past, craft new memories, and become a part of a story centuries in the making.

What’s Included:

From airport transfers, support vehicles and feed stations to all accommodation and meals, we have you covered…

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DISCOVER THE DIFFERENCE:

Where Support Team Excellence Transforms Your Cycling Adventure

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FUEL YOUR RIDE:

Explore our Tempting Feed Station Delights…

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Stage Breakdown

1

PROLOGO: TRANSFER ROME

We will greet you at Rome’s Fiumicino airport before transferring you, along with your gear, to Orvieto’s ancient centre.

After assembling your bikes, we can take a stroll through Orvieto’s cobbled streets to visit the stunning Duomo and explore the mysterious subterranean caves.

As the day draws to a close, we gather for team introductions, safety briefings, and event overview.

To culminate the day’s explorations, dinner awaits at our selected restaurant nestled within one of the subterranean caves, promising an unforgettable start to the Grand Tour journey.

2

 TAPPA 1: ORVIETO to ASSISI

100kms | 1,900m
62miles | 6200ft

Begin your Grand Tour Italia adventure with a 100km ride from Orvieto to Assisi. 

Cycle through the picturesque woodlands of Parco Fluviale del Tevere before pausing in the medieval towns of Todi and Bevagna to soak up Umbria’s rich legacy whilst enjoying the regional cuisine. 

The stage concludes in Assisi, famed for spiritual significance and architectural marvels. Explore the Basilica of St. Francis, a UNESCO World Heritage Site symbolising the town’s sacred past. 

End the day with a memorable dinner at the hotel’s restaurant, boasting a spectacular view of Assisi’s majestic skyline, relishing the memories of this remarkable first stage. 

3

TAPPA 2: ASSISI to CITTA DELLA PIEVE

90kms | 1,400m
55miles | 4600ft

This enchanting second leg of our Grand Tour Italia departs from Assisi and winds through the heart of Umbria to Citta della Pieve. 

The route leads through Deruta, celebrated for its exquisite ceramics, and then to Montegabbione, a medieval village nestled among hilly sceneries adorned with olive groves and lush meadows. 

Arrive at the picturesque Citta della Pieve, perched on a hill with a striking blend of medieval and Renaissance architecture. Your stay in Citta della Pieve is made exceptional at a hotel with royal connections, originally owned by Italian Royalty and now a jewel in the Wirth family’s collection. 

4

TAPPA 3: CITTA DELLA PIEVE to SIENA

110kms | 1,900m
68miles | 6200ft

Travel through quintessential Tuscan scenery, winding along the serene roads from Citta della Pieve to Siena. 

Discover Sarteano, where medieval streets wind around a castle rooted in Etruscan history, and explore Pienza, famed for pecorino cheese. 

Conclude in Siena, a city of medieval marvels, featuring the majestic Piazza del Campo, stunning Duomo, and historic Palazzo Pubblico. Here, history, tradition, and vibrant Tuscan culture blend seamlessly, offering an unforgettable experience. 

This stage promises immersion in Tuscany’s charm, from its ancient roots to its vibrant present, enriching your exploration through Italy. 

5

TAPPA 4: SIENA to SAN GIMIGNANO

90kms | 1,200m
55miles | 3900ft

A captivating cycling route through the heart of the Chianti region, celebrated for enchanting landscapes, world-class wines, and its deep cultural legacy. 

Begin your adventure in Gaiole in Chianti, a charming gateway into traditional Tuscan life surrounded by historic vineyards. Move on to Radda in Chianti, perched on a hill with medieval streets and ancient fortifications, and then continue to Castellina in Chianti, an idyllic spot to relish local gastronomy. 

Your ultimate destination is San Gimignano, a UNESCO World Heritage Site with a meticulously preserved medieval structure and 14 iconic towers, offering a captivating history along the Via Francigena. 

6

TAPPA 5: SAN GIMIGNANO to FLORENCE

100kms | 1,500m
62miles | 4900ft

The concluding stretch, from San Gimignano to a quaint town near Gino Bartali’s birthplace outside Florence, leads through classic Tuscan locales, providing glimpses into the region’s rich history and enduring charm. 

Panzano and Montefioralle – one of the ‘Borghi piu belli d’Italia’ – boast Gothic masterpieces and medieval walls, exuding a timeless allure. 

Greve in Chianti and the historic Greve Castle, offer panoramic views of vineyards and hills, connecting with the medieval origins of the Chianti Classico wine region. 

Cycling through these iconic landmarks not only showcases breathtaking scenery but also reveals layers of history and tradition, defining this unforgettable final leg of the Grand Tour Italia. 

7

PARTENZE: TRANSFER FLORENCE AIRPORT

As your adventure concludes, we will ensure a smooth transfer to Florence Airport, aiming for an arrival around 11am. 

To allow for any unexpected delays, consider scheduling your flight for late afternoon or early evening. Alternatively, extend your stay to explore vibrant Florence before your journey home. 

While we will be sad to bid you farewell, we look forward to sharing more incredible rides with you on future tours. 

1

PROLOGO: TRANSFER ROME

We will greet you at Rome’s Fiumicino airport before transferring you, along with your gear, to Orvieto’s ancient centre.

After assembling your bikes, we can take a stroll through Orvieto’s cobbled streets to visit the stunning Duomo and explore the mysterious subterranean caves.

As the day draws to a close, we gather for team introductions, safety briefings, and event overview.

To culminate the day’s explorations, dinner awaits at our selected restaurant nestled within one of the subterranean caves, promising an unforgettable start to the Grand Tour journey.

1

PROLOGO: TRANSFER ROME

We will greet you at Rome’s Fiumicino airport before transferring you, along with your gear, to Orvieto’s ancient centre.

After assembling your bikes, we can take a stroll through Orvieto’s cobbled streets to visit the stunning Duomo and explore the mysterious subterranean caves.

As the day draws to a close, we gather for team introductions, safety briefings, and event overview.

To culminate the day’s explorations, dinner awaits at our selected restaurant nestled within one of the subterranean caves, promising an unforgettable start to the Grand Tour journey.

2

 TAPPA 1: ORVIETO to ASSISI

100kms | 1,900m
62miles | 6200ft

Begin your Grand Tour Italia adventure with a 100km ride from Orvieto to Assisi. 

Cycle through the picturesque woodlands of Parco Fluviale del Tevere before pausing in the medieval towns of Todi and Bevagna to soak up Umbria’s rich legacy whilst enjoying the regional cuisine. 

The stage concludes in Assisi, famed for spiritual significance and architectural marvels. Explore the Basilica of St. Francis, a UNESCO World Heritage Site symbolising the town’s sacred past. 

End the day with a memorable dinner at the hotel’s restaurant, boasting a spectacular view of Assisi’s majestic skyline, relishing the memories of this remarkable first stage. 

2

 TAPPA 1: ORVIETO to ASSISI

100kms | 1,900m
62miles | 6200ft

Begin your Grand Tour Italia adventure with a 100km ride from Orvieto to Assisi. 

Cycle through the picturesque woodlands of Parco Fluviale del Tevere before pausing in the medieval towns of Todi and Bevagna to soak up Umbria’s rich legacy whilst enjoying the regional cuisine. 

The stage concludes in Assisi, famed for spiritual significance and architectural marvels. Explore the Basilica of St. Francis, a UNESCO World Heritage Site symbolising the town’s sacred past. 

End the day with a memorable dinner at the hotel’s restaurant, boasting a spectacular view of Assisi’s majestic skyline, relishing the memories of this remarkable first stage. 

3

TAPPA 2: ASSISI to CITTA DELLA PIEVE

90kms | 1,400m
55miles | 4600ft

This enchanting second leg of our Grand Tour Italia departs from Assisi and winds through the heart of Umbria to Citta della Pieve. 

The route leads through Deruta, celebrated for its exquisite ceramics, and then to Montegabbione, a medieval village nestled among hilly sceneries adorned with olive groves and lush meadows. 

Arrive at the picturesque Citta della Pieve, perched on a hill with a striking blend of medieval and Renaissance architecture. Your stay in Citta della Pieve is made exceptional at a hotel with royal connections, originally owned by Italian Royalty and now a jewel in the Wirth family’s collection. 

3

TAPPA 2: ASSISI to CITTA DELLA PIEVE

90kms | 1,400m
55miles | 4600ft

This enchanting second leg of our Grand Tour Italia departs from Assisi and winds through the heart of Umbria to Citta della Pieve. 

The route leads through Deruta, celebrated for its exquisite ceramics, and then to Montegabbione, a medieval village nestled among hilly sceneries adorned with olive groves and lush meadows. 

Arrive at the picturesque Citta della Pieve, perched on a hill with a striking blend of medieval and Renaissance architecture. Your stay in Citta della Pieve is made exceptional at a hotel with royal connections, originally owned by Italian Royalty and now a jewel in the Wirth family’s collection. 

4

TAPPA 3: CITTA DELLA PIEVE to SIENA

110kms | 1,900m
68miles | 6200ft

Travel through quintessential Tuscan scenery, winding along the serene roads from Citta della Pieve to Siena. 

Discover Sarteano, where medieval streets wind around a castle rooted in Etruscan history, and explore Pienza, famed for pecorino cheese. 

Conclude in Siena, a city of medieval marvels, featuring the majestic Piazza del Campo, stunning Duomo, and historic Palazzo Pubblico. Here, history, tradition, and vibrant Tuscan culture blend seamlessly, offering an unforgettable experience. 

This stage promises immersion in Tuscany’s charm, from its ancient roots to its vibrant present, enriching your exploration through Italy. 

4

TAPPA 3: CITTA DELLA PIEVE to SIENA

110kms | 1,900m
68miles | 6200ft

Travel through quintessential Tuscan scenery, winding along the serene roads from Citta della Pieve to Siena. 

Discover Sarteano, where medieval streets wind around a castle rooted in Etruscan history, and explore Pienza, famed for pecorino cheese. 

Conclude in Siena, a city of medieval marvels, featuring the majestic Piazza del Campo, stunning Duomo, and historic Palazzo Pubblico. Here, history, tradition, and vibrant Tuscan culture blend seamlessly, offering an unforgettable experience. 

This stage promises immersion in Tuscany’s charm, from its ancient roots to its vibrant present, enriching your exploration through Italy. 

5

TAPPA 4: SIENA to SAN GIMIGNANO

90kms | 1,200m
55miles | 3900ft

A captivating cycling route through the heart of the Chianti region, celebrated for enchanting landscapes, world-class wines, and its deep cultural legacy. 

Begin your adventure in Gaiole in Chianti, a charming gateway into traditional Tuscan life surrounded by historic vineyards. Move on to Radda in Chianti, perched on a hill with medieval streets and ancient fortifications, and then continue to Castellina in Chianti, an idyllic spot to relish local gastronomy. 

Your ultimate destination is San Gimignano, a UNESCO World Heritage Site with a meticulously preserved medieval structure and 14 iconic towers, offering a captivating history along the Via Francigena. 

5

TAPPA 4: SIENA to SAN GIMIGNANO

90kms | 1,200m
55miles | 3900ft

A captivating cycling route through the heart of the Chianti region, celebrated for enchanting landscapes, world-class wines, and its deep cultural legacy. 

Begin your adventure in Gaiole in Chianti, a charming gateway into traditional Tuscan life surrounded by historic vineyards. Move on to Radda in Chianti, perched on a hill with medieval streets and ancient fortifications, and then continue to Castellina in Chianti, an idyllic spot to relish local gastronomy. 

Your ultimate destination is San Gimignano, a UNESCO World Heritage Site with a meticulously preserved medieval structure and 14 iconic towers, offering a captivating history along the Via Francigena. 

6

TAPPA 5: SAN GIMIGNANO to FLORENCE

100kms | 1,500m
62miles | 4900ft

The concluding stretch, from San Gimignano to a quaint town near Gino Bartali’s birthplace outside Florence, leads through classic Tuscan locales, providing glimpses into the region’s rich history and enduring charm. 

Panzano and Montefioralle – one of the ‘Borghi piu belli d’Italia’ – boast Gothic masterpieces and medieval walls, exuding a timeless allure. 

Greve in Chianti and the historic Greve Castle, offer panoramic views of vineyards and hills, connecting with the medieval origins of the Chianti Classico wine region. 

Cycling through these iconic landmarks not only showcases breathtaking scenery but also reveals layers of history and tradition, defining this unforgettable final leg of the Grand Tour Italia. 

6

TAPPA 5: SAN GIMIGNANO to FLORENCE

100kms | 1,500m
62miles | 4900ft

The concluding stretch, from San Gimignano to a quaint town near Gino Bartali’s birthplace outside Florence, leads through classic Tuscan locales, providing glimpses into the region’s rich history and enduring charm. 

Panzano and Montefioralle – one of the ‘Borghi piu belli d’Italia’ – boast Gothic masterpieces and medieval walls, exuding a timeless allure. 

Greve in Chianti and the historic Greve Castle, offer panoramic views of vineyards and hills, connecting with the medieval origins of the Chianti Classico wine region. 

Cycling through these iconic landmarks not only showcases breathtaking scenery but also reveals layers of history and tradition, defining this unforgettable final leg of the Grand Tour Italia. 

7

PARTENZE: TRANSFER FLORENCE AIRPORT

As your adventure concludes, we will ensure a smooth transfer to Florence Airport, aiming for an arrival around 11am. 

To allow for any unexpected delays, consider scheduling your flight for late afternoon or early evening. Alternatively, extend your stay to explore vibrant Florence before your journey home. 

While we will be sad to bid you farewell, we look forward to sharing more incredible rides with you on future tours. 

7

PARTENZE: TRANSFER FLORENCE AIRPORT

As your adventure concludes, we will ensure a smooth transfer to Florence Airport, aiming for an arrival around 11am. 

To allow for any unexpected delays, consider scheduling your flight for late afternoon or early evening. Alternatively, extend your stay to explore vibrant Florence before your journey home. 

While we will be sad to bid you farewell, we look forward to sharing more incredible rides with you on future tours. 

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