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REF: #07900

Como - Cinqueterre - Tuscany Road Cycling Trip

This is an unique opportunity to cycle the most beautiful route of Italy during this 11 days/10 nights trip.

  • Half board hotel
  • Italian Alps —Cernobbio > San Quirico d'Orcia
  • Activity Type
    • With guide
    • Point to point
  • Groups up to 20
  • Features
    • Bar
    • Ensuite rooms
    • Family rooms
    • Garden
    • Hot tub
    • Indoor pool
    • Outdoor pool
    • Pool table
    • Private parking
    • Restaurant
    • Sauna
    • Secure bike storage
    • Steam
    • Table tennis table
    • Terrace
    • TV/DVD
    • Wifi



Tuesday 15 September

Pick up at Milan Malpensa Airport and check in at your hotel in Cernobbio. This beautiful town will be your starting point for your upcoming cycling trip in Italy. The tour leader will explain the coming activities and itinerary for this road cycling trip from Como to Cinque Terre to Tuscany. Overnight in Cernobbio Dinner included- Hotel Terzocrotto

Wednesday 16 September

On your first day you start in front of the hotel right on the shores of Lago di Como. Ride along three beautiful lakes: Lake Como, Switzerland’s Lake Lugano and Lake Maggiore. You will see many nice villas with huge gardens created in the 19th and 20th Century. Test your legs on the hills and cols we pass. You ride along scenic secondary roads that will take you across the border into Swiss territory! Crossing over into Switzerland, you descend few switchbacks and you ride along the quiet shores of Lake Lugano and finally we reach back our final destination, the Como lake side town of Cernobbio. This very pleasant town is the second home of George Clooney. Overnight is Cernobbio in Hotel Terzocrotto Dinner included. 110kilometers – 1200 climbing meters

Thursday 17 September

The morning ride along lake Como shores will take you towards the renowned town of Bellaggio. Only avid cyclists know that Bellagio is at the very bottom of the Giro di Lombardia’s last decisive climb of the “Madonna del Ghisallo” (length 6.6 miles - 1.811 feet of elevation gain - 5.2 % average grade), the little church of the patron saint of cyclist where you can admire the bikes of the great Fausto Coppi and Gino Bartali! Overnight is in Cernobbio Hotel Terzocrotto – no dinner

Friday 18 September

Transfer by van to the start of your ride into the Ligurian hills. You will face a though day in the saddle but you will be rewarded in the beautiful place of Rapallo. Placed in a panoramic position opposite to the ancient castle our Hotel Europa is just a few steps away from the seafront, the beaches and the “imbarcadero”: the starting point for ferries to Portofino, San Fruttuoso and the charming Cinque Terre. HotelEuropa-Rapallo – no dinner Distance of ride: 136 km/2300 m of total climbing.

Saturday 19 September

Riding out of Rapallo you will start an extremely scenic ride to Portofino riding along the Mediterranean passing Santa Margherita Ligure and Paraggi .. returning towards the sea village of Chiavari and Sestri Levante; a rather easy climb with great views at the top, the Passo del Bracco, used as TT for the Giro’s Centenary, will take us to our destination. Once reached the top of Passo del Bracco You will descend to Levanto which is the last village before Cinque Terre. Hotel in Levanto – Hotel Oasihotel– Dinner included Distance of ride: 82 km/1130 m of total climbing.

Sunday 20 September

Just out of the village Levanto we begin our ride into the magnificent Cinque Terre enjoying breath-taking views of the dramatic cliffs below and finishing in Portovenere with a spectacular view of the La Spezia gulf. Hotel in Lerici –Hotel Doriahotel– Dinner included Distance of ride: 59 km/960 m of total climbing.

Monday 21 September

You start off with a beautiful ride around the Lerici peninsula to the village of Montemarcello descending into Bocca di Magra. You will ride along the Ligurian Sea to Forte dei Marmi where you will leave the coast … you cycling through Camaiore, climb up to Montemagno and finally you will reach your final destination: Lucca. Hotel in Lucca – Hotel Apalazzobusdraghi – No dinner. Distance of ride: 92 km/700 m of total climbing. Hotel location: inside the walled city of Lucca.

Tuesday 22 September

On today’s ride you will pass typical Tuscan villages like Compito, Bientina, Forcoli, Peccioli, La Sterza, Vicarello, Il Castagno before we arrive San Gimignano. Hotel in Gimignano. Hotel Leonbianco – Dinner included. Distance of ride: 90 km/725 m of total climbing Hotel location: in San Gimignano’s square

Wednesday 23 September

Who in the world today would not know anything about the Chianti red wine? Today you will ride to Radda in Chianti with climbing 10 km up to Castellina in Chianti and cycling through multiple vineyards. Your Hotel is located in the quiet village of Radda in Chianti, a Relais, and part of the Luxury chain Hotels. Todays villages : San Gimignano, Le Grazie, Quarraia, Lano, Mensanello, Santa Giulia, Strove, Abbadia, Monteriggioni, Castellina Scalo, 10 km climb up to Castellina in Chianti, Radda in Chianti. Hotel in Radda in Chianti- Hotel Vignale – Dinner included. Distance of ride: about 75 km/1000 m of total climbing.

Thursday 24 September

From the typical Chianti countryside to the beautiful Siena’s gentle rolling hills. Dinner at a local place. Hotel location: San Quirico d’Orcia- Hotel Casalemmi- Dinner included- Distance of ride: 103 km/1630 m of total climbing.

Friday 25 September

Unfortunately it’s your last day! It’s time to say goodbye a good flight back home or else a pleasant stay in Italy. Transfers to the Airport Milan Malpensa or Pisa airport will be made by the Tour guide. Or to other various airports on the way back.

We are able to provide extra nights on request.


You will be staying in the following hotels:

Hotel Terzocrotto

otel Terzo Crotto is a farmhouse surrounded by a garden in Cernobbio’s centre, 400 m from the shores of Lake Como and a few minutes’ walk from the city centre. It offers free WiFi and air-conditioned rooms. Decorated with simple wood furniture, all rooms at Terzo Crotto feature marble floors, a fan and a flat-screen TV with Sky TV. The private bathrooms come with a hairdryer and toiletries. The Crotto’s restaurant serves Italian cuisine and specialities from the Lake Como area. An extensive list of local and international wines is available. Staff are available 24 hours a day and offer storage space for your ski equipment. Terzo Crotto Hotel is a 10-minute walk from the patrician Villa d’Este and 3 km from the Como Nord exit of the A9 motorway.

Hotel Europa

Dating back to 1877, Europa Hotel is opposite Rapallo Castle and a few steps from the beach. Guests can reserve in advance a free 90-minute wellness circuit in its Plinio Thermarium spa, which is complete with sauna and Turkish bath. Europa Hotel Design Spa 1877 is 5 minutes’ walk from Rapallo Train Station and near the dock for boats along the coast and to the Cinque Terre. All air-conditioned, rooms here come with satellite TV, a minibar and a private bathroom with a hairdryer and toiletries. A buffet breakfast is served each morning and the hotel’s restaurant has its own garden. You will also find a lounge bar, fitness centre and the Plinio Auditorium for meetings.

Oasi Hotel

Oasi Hotel is just a 5-minute walk from Levanto beach and Train Station,very close to the centre. It offers elegant and bright interiors and rooms, and serves a varied American breakfast. Decorated with refined touches, along with light-wood floors and furniture, all rooms have free Wi-Fi access, air conditioning and an LCD TV. Some rooms offer a balcony or direct access to the private garden. English-speaking staff at Hotel Oasi are available 24 hours a day and can recommend restaurant, check train schedules and provide tourist information. From Levanto Station, you can get a train and reach the 5 towns of Cinque Terre in less than 15 minutes.

Doria Park Hotel

Doria Park Hotel offers free parking and is just outside the pedestrian area, only 2 minutes’ walk from Lerici historic centre via a staircase. The terrace offers stunning views of the Gulf of Poets, the castle, and the old town. Rooms at Doria Park Hotel are air conditioned and feature an LCD TV, minibar, and free tea and coffee. A generous buffet breakfast is served on the terrace until 12:00. Offering local specialities, the hotel’s restaurant is open at dinner. The hotel is easily reached following the road signs for Tellaro. The beach is just a 5 minutes’ walk away.

Hotel Apalazzobusdraghi

Set on Via Fillungo in the heart of Lucca, A Palazzo Busdraghi is an elegant 16th-century building offering en suite rooms with free Wi-Fi, air conditioning, a minibar, and a satellite flat-screen TV. Buffet breakfast is served until 11:00. Rooms have a classic décor with parquet floors and antique furniture, while some include a spa bath. Breakfast includes cakes, sweet or savoury crepes, cereals, and fresh Tuscan bread and pastries. Gluten-free food is available on request. A Palazzo Busdraghi Residenza D’Epoca is under new management since 2012, when it was refurbished. Staff will be more than happy to provide tips to get the most out of your stay in Lucca. Discounts are available at wellness centres in San Giuliano Terme and Monsumanno.

Hotel Leonbianco

Dating back to the 11th century, Leon Bianco is in Piazza della Cisterna, one of San Gimignano’s main squares. During summer, breakfast is served on the quiet, relaxing terrace. Rooms have original features such as wood-beamed ceilings and modern amenities including air conditioning and satellite TV. WiFi access is available in the lobby and rooms. There is also an internet point. Breakfast at is buffet style, while the bar serves drinks out on the terrace in warm weather. The hotel also features a fitness centre and billiards room. You can drive to the hotel, where you are granted a 20-minute parking permit to unload luggage. The shortest route is via the Porta San Jacopo city gate. Public parking is available outside the historic walls, between 5 and 10 minutes’ walk away. A public shuttle is active between April and October.

Hotel Vignale

Relais Vignale is a charming country house of the 17th century located in the heart of the Chianti Classico area, with panoramic views across the Tuscan countryside. The outdoor swimming pool is set in a floral garden, and the restaurant features a terrace. The centre of Radda is 2 minutes’ walk away. The building was renovated according to the original architecture, and offers the standards of a 4-star hotel. Rooms are rustic yet elegant, each is individually designed, and comes with air conditioning and satellite TV. Some rooms are in the annex building. The Vignale includes a collection of antique furniture, frescoed ceilings, and grand fireplaces. There is also a TV room, lounge bar, and library. Wi-Fi is available and there is a free internet point in the lobby. The restaurant is open to the public and specialises in a mix of traditional and modern Tuscan dishes and fine local wines. Breakfast is buffet style. The property offers free parking and is 1 hour’s drive from both Florence and Siena. At reception you can organise visits to the cellar of the Castello di San Donato in Perano, 4 km away.

Casa Lemmi

Set in San Quirico d’Orcia, Casa Lemmi is a residence of Norman origins. It features an ancient, stone-wall cellar with an indoor pool, facing the garden. The rooms open internally to a staircase of Roman origins, restyled in the 19th century with a dome to let the sun and light flow in. Each room is individually furnished and offers views of San Quirico d’Orcia and the Val d’Orcia. Rooms come with air conditioning, satellite TV and an electric kettle. Casa Lemmi faces Mount Amiata on one side and the Collegiata Church on the other. Throughout the last 1000 years, the property has been a refuge for the Templars, an imperial fortress, a convent and a fortified palace. Casa Lemmi is a 50-minute drive from Siena and 13 km from Montalcino. The spa town of Bagno Vignoni is 5 km from the property, while Chianciano Terme is a 30-minute drive away.


This road cycling trip features many highlights, your start will be in the Como lake side town of Cernobbio. This very pleasant town is the second home of George Clooney. Ride along three beautiful lakes: Lake Como, Switzerland’s Lake Lugano and Lake Maggiore. A trip to Lake Como is not complete without a ride up to Ghisallo, visiting the museum and the chapel of La Madonna del Gisello is a must do for every cyclist, From the Italian lake district you continue to the Liguarian hills of Cinque Terre. Out of the village of Levanto you will begin our ride into the magnificent Cinque Terre enjoying breathtaking views of the dramatic cliffs below and finishing in Portovenere with a spectacuar view of the La Spezia gulf. After the Cinque Terre area the cycling trip continues to beautiful Tuscany!