Day 1


Sunday, September, 13
25 mi / 1900 ft

Upon your arrival into Pisa, the SV shuttle will transfer you our first night’s hotel in the historical walled city of Lucca. This afternoon, our Italian adventure begins with a prologue in the form of a quick, undulating spin from central Lucca. A perfect opportunity to get to know your guides and your riding mates for the week before enjoying your first night in Italy. After our short ride, we will gather this evening for a group orientation to go over the daily itinerary and plan for the week followed by a typical Tuscan evening meal.

Overnight: Albergo Celide

Day 2


Monday, September 14
88 mi / 9,500 ft

On our first day of riding we’ll roll out of the northern Italian city of Lucca, and the first few hours will attest to the ruggedness of this country’s mountains and roads. We’ll climb nearly 1,000 meters before enjoying a ripping descent into the quaint and beautiful mountain village of Buti. And flatter terrain will carry us to the magnificent medieval city of San Gimignano, where we’ll take our time winding through some of the cobbled roads and quite possibly take a gelato on board. With Romanesque arches and towers perched on a lush green hillside, San Gimignano is something no traveler should miss.

After a quick break in that beautiful city, we’ll ride the home stretch to our destination for the night, the historic and classically Italian city of Siena, where we’ll dine in one of the region’s finest establishments. In the form of a 19th-century trattoria, the Osteria de Logge is a true gem. Owner and chef Gianni Brunelli is in a class of his own and goes to great lengths for the perfection of his craft, including personally raising his own Sienese belted pigs.

We’ll revel in the unique culture of Siena, a city where, twice a year in summer, one of the most famous and historic horse races in the world, the Palio di Siena, runs right through the city’s piazza. It’s quite common for more than a few of the riders to be flung from their horses in the corners, leaving those horses to charge through the finish line on their own.

Overnight: Palazzo Ravizza

Day 3


Tuesday, September 15
90mi / 9,970 ft
Major Climb: Monte Luca

Departing the famous city of Siena we continue to the heart of Chianti, a land that has become world famous for its food and, of course, wine, where we dive into some of the most beautiful riding in Europe. We’ll enjoy the unpaved sections of the Strade Bianche, the one-day minor Classic won in 2019 by Julian Alaphilippe. Alaphilippe put in a heroic effort in that race, stunning a fatigued Jakob Fuglsang with an impressively punchy attack after a long, hard day of racing. The young Frenchman certainly knows how to find another gear.

We’ll make one main climb for the day, the Monte Luca, before descending on to the roads featured in the stylish and increasingly popular vintage bike race, L’Eroica. Started in 1997 with only 98 participants, the nostalgic event has grown vastly, with over 5,000 lining up last year on steel frames and wearing vintage jerseys to enjoy one of the best courses in the world. Nearing the end of our ride, we’ll climb out of the city of Moggiona into a quaint village in the hillside, where we’ll stay for the night and rest up for the biggest day of our trip.

Overnight: to be confirmed

Day 4


Wednesday, September 16
85 mi / 13,500 ft
Major Climbs: Passo dei Mandrioli, Monte Carpegna

It is today that we really begin our pilgrimage in honour of Marco Pantani. Widely recognised as one of the best climbers ever to race a bicycle, he won both the Giro and the Tour de France in the same year.

From his hometown of Cesenatico, even as a child Pantani used to ride into the hills around Monte Carpegna. 2014 marked the 10th anniversary of the death of Il Pirata at a hotel in the off-season seaside resort of Rimini, and the 2014 Giro d'Italia honoured him with a stage that crossed Carpegna. It’s a gem of a climb, with a maximum gradient of 22%, and one that Pantani regularly trained on, testing himself to gauge fitness. “It’s on Carpegna that I’ve prepared for all my victories – Carpegna is all I need,” Pantani said.

After a tough day in the hills we reach the World Heritage Site of Urbino for the night, where the 15th-century Palazzo Ducale houses one of the most important collections of Renaissance artwork.

Overnight: Hotel Mamiani

Day 5


Thursday, September 17
77 mi / 12,105 ft
Major Climbs: Monte Petrano, Monte Nerone

The Queen Stage of this randonnee takes in the climbs of Monte Petrano and Monte Nerone, two-thirds of Stage 16 of the 2009 Giro d’Italia (we ride the third climb, Monte Catria, tomorrow). Riders described Stage 16 as one of the toughest stages of a Grand Tour in recent times.

Bradley Wiggins (then riding for Garmin-Slipstream) and Tom Danielson, had been dropped even before reaching Monte Nerone, while Yaroslav Popovych spent much of the day in the break and then attacking solo. He was caught by stage winner, Carlos Sastre, inside the last 3km, who beat Danilo Di Luca and Denis Menchov to the line.

We stay in the Umbrian town of Gubbio tonight, an ancient town occupied since the Bronze Age and known for its Gothic architecture.

Overnight: Park Hotel Al Cappuccini

Day 6


Friday, September 18
76 mi / 8,780 ft
Major Climb: Monte Catria

This penultimate stage may not have the stats to match yesterday’s Queen Stage, but do not underestimate the Monte Catria. It reaches 1,415m with spectacular views across the Central Apennines.

At Castelraimondo we continue our gastronomic tour with a stay at Borgo Lanciano, home to the famed restaurant, I Due Angeli. Here we will be served traditional cuisine from the Marche region, while the wine list offers the best from a cellar stocked with some of the finest Italian producers.

Overnight: Borgo Lanciano

Day 7



Saturday, September 19
86 mi / 13,105 ft
Major Climb: Piano Grande

The final day of our journey takes us to the Adriatic coast and the town of Ascoli Piceno, via the stunning Piano Grande and the Parco Nazionale dei Monte Sibillini, an area famed for its outstanding natural beauty and for Umbria’s famous lentils, Lenticchie di Castellucio.

We arrive into Ascoli Piceno, the capital of the Marche region, with around 50 beautiful towers around the stunning Piazza del Popolo. Piceno is a reference to the ancient tribe of Piceni, who dwelled in the region until they were conquered by the Romans in the 2nd century BC.

We’ll relax in Ascoli and celebrate our achievements with a glass (or two!) of Rosso Piceno Superiore. It is said that even the great general Hannibal refreshed his troops with wine of the Marche region.

Overnight: Palazzo dei Mercanti



Sunday, September 20

We can provide shuttles to either Abruzzo or to Rome on the last day of the trip, September 20th. We will drop off at Abruzzo by 10:30 am and then Rome 4:00 PM.

  • Abruzzo International Airport (PSR) - 1h30m transfer

  • Rome-Leonardo da Vinco International Airport (FCO) 3h45m transfer (additional fee required for this transfer)