Milan to Rome | CycleVentures

Milan to Rome

Afterall...all roads lead to Rome.

Like an overstuffed cannelloni, this trip is crammed with amazing riding in four unforgettable regions: Lombardy, Emilia-Romagna, Tuscany and Lazio. Departing musically-rich Cremona in the flat Po valley we cycle through the quiet Apennine mountains with visits to proud Parma and Lucca. Next up is quintessential Tuscany with its postcard-perfect landscapes, world-class art and superb cuisine where we’ve included an exploratory day in Siena featuring a myriad of perfect riding options to classic Tuscan towns like San Gimignano and Radda in Chianti. We continue south to the hilltop town of Montalcino, famous for its red grape, the Brunello di Montalcino, and then diving into the Lazio region and Rome. 



Day 1: Arrive to Milan, Italy. Transfer to Cremona.

Arrive at Milan Malpensa Airport and transfer to Cremona. Located on the left bank of the Po river, Cremona is known for its lovely Piazza del Comune and importantly as a music centre. Claudio Monteverdi, father of opera, was born here in the 16th century and the heritage left by three master violin makers, Andrea Amati, Nicolò Amati and Antonia Stradivari have made Cremona the centre for the world's top stringed instruments today.

Day 2: Cycle Cremona to Castelnovo ne Monti — 118 km

Begin our journey along the flat roads of the agricultural lands along the Po river. We’ll lunch in the attractive town of Parma, famous for it’s cheese, prosciutto, Lamborghinis, Romanesque buildings and a composer named Verdi. This afternoon we pedal up gentle slopes into quiet hills of the Apennine foothills where cattle graze and few cars pass.

Day 3: Cycle Castelnovo ne Monti to Lucca. — 112 km

A morning of climbing as we cross the remote Apennines mountains. Our first appointment is the Passo Pradarena (1579 meters) followed by a spectacular 12 km descent. After lunch in Castelnuovo di Garfagnana it’s a cruisy mostly downhill 44 km to the vibrant and lovely city of Lucca. Completely encircled by Renaissance walls and featuring handsome piazzas and shady promenades, Lucca is a pleasure to explore.

Day 4: Cycle Lucca to Siena — 103 km

A spectacular day of riding as we cross Tuscany on quiet roads with few cars. There are options to extend your ride today; you could have your morning coffee in the shadow of Pisa’s famous leaning tower or sip a glass of Chianti in the village of Radda? Either way, you’ll end your great day with a final climb to spectacular Siena.

Day 5: Explore Siena — 90 km (optional)

Choosing what to do on this day will be the greatest challenge. Siena is effectively a giant open-air museum with a long list of medieval monuments and Sienese art. Its fan-shaped Piazza del Campo is regarded as one of Europe’s greatest medieval squares while it’s cuisine is worldclass. The riding choices are endless as Siena is situated in the heart of Tuscany and it’s famous cycling routes.

Day 6: Cycle Sienna to Montalcino — 54 or 102 km

We’ve kept today shorter as there are a myriad of amazing options. You could spend more time in Siena this morning and leave after lunch? Or arrive early to our destination, the pretty hilltop town of Montalcino and spend the afternoon wine tasting at a local Brunello di Montalcino or nearby Nobile di Montepulciano vineyards? Or, choose a longer loop via Tuscan’s amazing roads.

Day 7: Cycle Montalcino to Viterbo — 105 km

Heading south we bid farewell to Tuscany and welcome Lazio with its pale golden light and ancient stone villages, past breathtaking vistas to Viterbo. Originally an Etruscan settlement, it became the papal centre during the 13th c. and today is recognized for having maintained the finest preserved medieval buildings in all of Italy.

Day 8: Cycle Viterbo to Cerveteri. Transfer to Rome Airport hotel. — 70 km

You’ll feel the pull of Rome as the landscape flattens and you pedal effortlessly past beautiful checkerboard fields on a ribbon of pastoral country roads. Once in Cerveteri we’ll load the bikes and transfer to our hotel near Rome’s airport. This afternoon we’ll pack our bikes and head into the city for our last night’s dinner.

Day 9: Transfer to Rome Marco Polo Airport, arrivederci!

Transfer to Rome’s Marco Polo Airport for flights home. Or, extend your trip and explore Rome.


Dates: Friday September 7, 2018 to Saturday September 15, 2018
Duration: 9 days, 8 nights
Joining In: Milan, Italy (departing Rome)
Skill Level: Avancé
Total Distance: 700 km
Land Cost: $3895 CAD

Ride Map

See the approximate route of the trip on Google maps. Register today!

Skill Levels

Here are descriptions of the skill & fitness levels required for our cycling trips.  Remember, the support van is never far away if you need a lift and on all of our trips you can always ride more if you wish. We’re here for you.


Flat and rolling terrain and shorter riding days of approximately 50–70 km. Elevation gains of up to approximately 700 meters daily. Suitable for beginner and intermediate cyclists. Stronger riders looking for more kilometers can extend most days.


Rolling terrain with some bigger climbs and averaging approximately 70-100 km daily. Elevation gains of approximately 700 meters and above daily. Suitable for fit beginners, strong intermediate riders and above. A triple crank or compact crank is recommended. Stronger riders looking for more kilometers can extend most days.


Long riding days over 100 km daily and long climbs with steep sections can be expected. Caters to strong cyclists or riders in good physical condition seeking a mental and physical challenge. Elevation gains of approximately 1000 meters and above daily.