Day 1 Saturday/ 3rd October - Arrivals into Milan Malpensa.  Transfer to Lake Como.  Build bikes. 
Short warm up loop (approximately 40km) to Swiss border and back to hotel .
Stay: Dandelion Como Suites & Park https://www.dandelioncomo.it/

Ride 115km/450 Como to Pavia passing via Milan's Duomo . Cycle a mix of lake scenery, urban architecture, historic canals, and peaceful countryside
Stay: Hotel Il Casale Denari.  http://www.ilcasaledenari.it/ 

Ride 108km/ 329m Pavia to Polesine parmense, visiting Cremona . quite scenic, mostly flat, and rich in history and rural charm. Cremona itself: a great spot to explore. Known for its violin-making history (think Stradivari), it's peaceful, elegant.
Stay: Antica Corte Pallavicina Relais.  http://www.anticacortepallavicinarelais.it/ 

Ride 115km/1,700m from Polesine parmense to Pontremoli, passing through Fidenza.  . a transition from very flat lowlands into more gentle slopes that are a prelude to the Apennines. Climbs include Monte Cassio and Passo Della Cisa.
Stay: Cà del Moro Resort https://www.cadelmororesort.it/?utm_source=GB&utm_medium=organic 

Ride 125km/1,700m from Ponteremoli to Lucca . The terrain climbs gently as you move north/northeast into the Garfagnana region, with rolling hills and increasing elevation.You'll pass through medieval villages, forested zones, and narrow mountain roads and past the Devil's Bridge. Climbs include the Passo dei Carpinelli.  The route feels very much like a pilgrimage trail, rich in history. typical of Appennini / Apuan foothills. 
Stay: Hotel Ilari, Lucca.

Ride 87km/1,100m Lucca to San Gimignano. a perfect taste of Tuscany: a mix of flat river valleys, rolling hills, and a finishing crescendo on one of the region's most iconic hilltop towns.
Stay: Relais Santa Chiara 

Day 7 Ride from San Gimignano  to Siena 68km/1000m. Passing through many beautiful Tuscan villages.  Generally, short rolling hills.
3 night Stay: Hotel Certosa di Maggiano https://www.lacertosadimaggiano.com/ 

Day 8.Saturday - Day off in Siena
Optional private guided city tour
Stay: Hotel Certosa di Maggiano https://www.lacertosadimaggiano.com/ 

Day 9.Sunday - Strade Bianche ride 138km/2,100m. cycling stripped back to its essentials. Dust, grip, rhythm, and timing. No hiding, no coasting, and definitely no pretending. It is not about speed alone. It's about control, patience, and making peace with the dust. A beautiful struggle, in the best possible setting.
Stay: Hotel Certosa di Maggiano https://www.lacertosadimaggiano.com/ 

Ride 106k/1,800m from Siena to San Casiano dei Bagni passing through San Quirico d'Orica. rolling Tuscan ride that feels harder than the profile suggests.  Leaving Siena, the roads quickly open into classic countryside with gentle but constant undulation. It is never flat for long, which makes the early kilometres ideal for settling into a steady rhythm. Traffic fades and the scenery takes over.The run into San Quirico d'Orcia is a standout. Cypress-lined hills, vineyards, and wide Val d'Orcia views create one of the most iconic stretches of the day. The town itself is calm and elegant, perfect for a brief roll-through or coffee stop.
After San Quirico, the climbing becomes more noticeable. Expect several steady climbs of 10 to 20 minutes, mostly moderate gradients with a few sharper ramps. Nothing extreme, but the elevation gain accumulates.
The final approach into San Casciano dei Bagni finishes with a sustained climb into the hilltop village. It is a controlled, honest effort that feels well earned, with big views and a strong sense of arrival at the end of a proper Tuscan day on the bike.
Stay:  Fonteverde https://www.fonteverdespa.com/ 

Cycle 118km/1,555m San Casiano dei Bagni to Sutri passing through Viterbo. A long, flowing transition day that trades Tuscany for northern Lazio, with one proper climb to give it structure.Leaving San Casciano dei Bagni, the terrain rolls gently at first, easing you south through quiet roads and open countryside. The riding feels relaxed early on, with long stretches where rhythm matters more than power.
The approach to Lake Bolsena is a highlight. Wide views open up as the lake appears, calm and expansive, before the road tips upward into the Passo di Monte Panaro. The climb from Bolsena is steady and well paced rather than steep, a sustained effort that rewards patience. Near the top, the views back over the lake are worth a quick glance, legs permitting.
From there, the ride becomes faster and more fluid. Descending and rolling terrain leads toward Viterbo, a lively, historic town and a natural midpoint. Expect a touch more traffic here, but nothing overwhelming.
After Viterbo, the landscape grows quieter again, with long, exposed sections and gentle rises that slowly wear on the legs. The final kilometres into Sutri are not dramatic, just honest riding, but arriving in the ancient hill town feels like a quiet victory after 118 km of composed, scenic mileage
Stay: Antico Borgo di Sutri https://www.anticoborgodisutri.it/

Ride from Sutri into Rome. 70km/750m.  15km gravel 15Km bike path into Rome. A shorter day on paper, but one that finishes with a sense of occasion.Leaving Sutri, the route rolls gently through quiet countryside, with low, steady climbs that keep the legs engaged without ever feeling demanding. The early kilometres are calm and rural, a nice contrast to what lies ahead. Midway, the ride shifts onto around 15 km of gravel. It is generally rideable and scenic rather than technical, adding texture to the day and a welcome change of pace. Smooth lines, relaxed handling, and a bit of dust on the calves.From there, the transition into the 15 km bike path into Rome is seamless.
Stay 2 nights: Hotel Horti 14. https://www.horti14.com/

Day 13.Thursday 15th October - Day off in Rome.
Stay: Hotel Horti 14. https://www.horti14.com/

Leaving Rome we ride to Fiuggi. 91km/1,507m. A deceptively tough day that leaves the city behind and heads straight into the hills.Departing Rome, the opening kilometres are relatively calm, often using quieter roads and paths to escape the urban sprawl. It does not take long before the terrain begins to rise and the ride takes on a more rural, Apennine feel.
The climbing is steady and cumulative rather than sharp, with a clear sense of gaining altitude as the day progresses. The unpaved sections, around 8.4 km in total, are generally manageable and scenic, more about focus and line choice than outright difficulty. They add character without breaking the flow. Short cobbled sectors, roughly 1.9 km, appear along the way, enough to rattle the bike and keep things interesting, but never for long.
As you approach Fiuggi, the final climbs become more defined. Nothing brutal, but after 90 km and over 1,500 metres of gain, they demand patience and pacing. Arriving in Fiuggi feels earned, a classic hill-town finish after a varied day that mixes smooth tarmac, rougher textures, and a gradual transition from city to mountains.
Stay: Silva Hotel Splendid http://www.silvasplendid.it/ 

Cycle 98km/971m from Fiuggi to Cassino.  A longer, more flowing day that gradually trades altitude for distance, with a memorable finish.
Leaving Fiuggi, the route descends and rolls through quieter roads, allowing the legs to open up after the previous day's climbing. The terrain is never flat for long, but the elevation gain comes in gentle waves rather than sustained efforts. Mid-ride, the landscape feels increasingly southern and open, with wide valleys, farmland, and long stretches where pacing and efficiency matter more than power. It is a day that rewards patience and smooth riding.
The defining moment comes at the end. From Cassino, the climb to the Abbazia di Montecassino rises clearly above the town, a steady, exposed ascent that feels symbolic as much as physical. The gradients are manageable, but after nearly 100 km, it demands respect. Reaching the abbey delivers sweeping views and a powerful sense of arrival, history layered thickly into the final metres of the ride.
Stay: Hotel Continental Cassino 

Ride 86km/776m from Cassino to Telese Terme. . A mix of valley floors, gentle foothills and occasional steeper rolling sections from the Liri valley toward the Telesina valley. Telese Terme is a thermal spa town in the Campania region known for its sulphur springs and wellness facilities. It sits in the Telesina valley at the foot of Monte Pugliano, making it a great recovery spot after a ride.
Stay:  Aquapetra Resort Spa http://www.aquapetra.com/ 

Cycle 68.4km/1,400m from Telese Terme to Borgo San Gregorio.   The route from Telese Terme into the Matese mountains heading toward San Gregorio Matese is long and climbs progressively from the Calore valley into more elevated terrain. Borgo San Gregorio is a scenic wine estate and boutique hospitality spot in Sorbo Serpico, in Campania's wine country
Stay: Feudi di San Gregorio https://borgosangregorio.com/ 

Oct 20th Cycle 112km/1,500m from Borgo San Gregorio  to Santa Maria di Castellabate. Rolling hills of Irpinia down toward the Gulf of Salerno. Santa Maria di Castellabate sits right on the Tyrrhenian Sea, part of the larger Cilento and Vallo di Diano National Park. It's a classic beach town with a little port, sandy coves, and emerald water that's perfect for a well-earned dip after a long ride
2 night Stay: Approdo http://www.approdothalassospa.com/

Oct 21st- relax by sea day

Ride 134km/2,479m from Santa Maria di Castellabate to Maratea . You roll out of Santa Maria di Castellabate with the sea close by and legs still optimistic. The first section through the Cilento National Park is classic southern Italy. Quiet roads, olive groves, pine forests, and small villages perched just high enough to remind you gravity is real.
After Acciaroli and Pioppi, the rhythm settles into a pattern. Short climbs, flowing descents, repeat. The roads are generally good, traffic is light if you stay off the main arteries, and the views keep distracting you from your heart rate.Heading south toward Sapri, the coastline becomes wilder and more dramatic. Cliffs drop straight into deep blue water, and the road clings to the landscape in that effortless Italian way that makes engineers look like poets.Crossing into Basilicata, the terrain tightens. The final approach to Maratea includes a longer, more sustained climb away from the coast before plunging back down toward town. It's not brutal, but after a long day it asks for focus and decent pacing. Then suddenly, there it is. Maratea, spread across the cliffs, with the Tyrrhenian stretching endlessly below. A proper finish.
Stay: Hotel Murman http://www.hotelmurmann.it/ 

Cycle 114km/1,980m from Maratea inland to Roggiano Gravina. Thos is a proper transition ride. You leave the sea behind, head inland, and trade coastal drama for big skies, quiet roads, and that deep southern-Italian calm that settles in once the climbing begins. The day starts with a climb straight out of Maratea. There's no warm-up. You gain altitude quickly as the road pulls you away from the Tyrrhenian, with occasional backward glances that remind you why Maratea is called the Pearl of the Tyrrhenian. Take them. They're free speed for morale. Once you crest, the air cools and the noise disappears. You're officially inland now. Through Basilicata, The middle section is where the ride earns its depth. Forested stretches, open plateaus, and long, quiet roads that feel built for endurance riding. Gradients are mostly manageable, but the distance starts to speak. This is a pacing day, not a hero day.
   Villages appear just often enough for espresso, water, and the kind of polite curiosity reserved for cyclists passing through. Expect curious looks, not questions.

Crossing into Calabria, As you move toward Roggiano Gravina, the landscape opens again. Olive groves, farmland, and gentle rollers replace the mountain feel. The riding becomes smoother, faster, and more rhythmic, a welcome change after the earlier climbing. The final kilometres are deceptively demanding. Nothing steep, but by now your legs know exactly how long you've been out. Roggiano Gravina is quiet, authentic, and refreshingly unpolished. It's the kind of place where the ride ends without fanfare, which somehow makes it better.
Stay: Hotel Palazzo Salerno http://www.hotelpalazzosalerno.it/ 

From Roggiano Gravina to Biafora Resort (Sila National Park) is 91km/1,990m and feels like a quiet exhale after the previous big stages. It's still southern Italy, still honest riding, but with a calmer rhythm and a refined finish. This is classic inland Calabria. Not flashy, not rushed. The gradients are friendly, but constant enough to keep you honest.
Stay: Biafora Resort & Spa https://www.biafora.it/ 

Cycle 77km/1,100m to  Tiriolo on one of those stages that feels quietly epic. High plateau, big forests, then a dramatic drop toward the narrow waist of Calabria where two seas almost meet.  Leaving Biafora, you're riding in air that feels noticeably cooler and cleaner. The Sila plateau is wide and calm, with long pine forests, open meadows, and roads that seem designed for rhythm rather than aggression. As you move west toward Tiriolo, the land begins to tilt. Forest gives way to open hills, views stretch out, and suddenly Calabria reveals its scale. On a clear day, you can sense both the Tyrrhenian and Ionian seas long before you see them. The riding becomes more dynamic here. Short climbs, flowing descents, and that satisfying feeling of moving from one world into another.
Stay: Hotel Residence Due Mari http://www.duemari.com/ 

Ride Tiriolo to Tropea. 83km/1,010m on a classic Calabrian stage short enough to ride with intent, yet varied enough to stay interesting, and with a finish that feels almost unfairly beautiful. As you head west, the landscape softens into olive groves and low hills. The climbing comes in short, honest efforts rather than long slogs. The final section into Tropea is a highlight. A long descent, sweeping bends, and the sea slowly expanding in front of you. This is the kind of run-in that makes you forget the numbers and focus on the moment.Then suddenly you're there. White sand, turquoise water, and cliffs that look almost staged.
2 nights Stay: Il Borghetto di Tropea  http://www.ilborghettoditropea.it/

On your final ride  you cycle  77km/1,508m  to Scilla near Villa San Giovanni and enjoy your first views of Sicily and a coastal finale with real presence. It's not long, but it's textured, dramatic, and finishes with Sicily almost close enough to touch. The road traces the coastline south, alternating between elevated viewpoints and small beach towns. The riding never settles into a flat rhythm. That's the charm. Gradients rise and fall in quick succession. Nothing long, but enough to keep you engaged and quietly working.Short, punchy, and visually rich, with a finish that feels like the edge of the map. We transfer back to Tropea after a celebratory drink arriving with plenty of time to box your bikes and enjoy one last final meal together.
Stay: Il Borghetto di Tropea  http://www.ilborghettoditropea.it/ 

As prearranged we will assist in getting you to where you ned to catch your flights out of Reggio Calabria or possibly Lamezia Terme.