+44 (0)1506 635399 info@hookedoncycling.co.uk
+44 (0)1506 635399 info@hookedoncycling.co.uk

Coast to Coast by Road Bike

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Homepage > Italy > Coast to Coast by Road Bike
  • Duration: 8 or 10 Nights
  • Difficulty: Level 3 (Level 4 optional)
  • Tour Type: Self Guided
  • Availability: Daily April to October
  • Location: Fano

Italy Coast to Coast Road Bike

Tour Details

Welcome to Hooked on Cycling holiday and our cycling holiday in Italy which takes you by bike from the Adriatic coast in the east to the Tuscan coastline in the west. This fabulous biking vacation takes you from Marche through the Umbrian hills and onto the Tuscan mountains before descending to the blue sea of the Tuscany coastline. This independent cycle tour (self-guided) has been graded level 3 as there are a number of climbs to navigate but daily distances are never too extreme. You will be rewarded with stunning views, UNESCO Heritage sites, medieval fortified villages, and of course fabulous Italian hospitality and wine. 

Most days have a long and short option

Starting Location


Price Includes

  • 8 or 10 nights bed breakfast
  • 3 star hotels and guest houses
  • Luggage transfers
  • Maps
  • Welcome meeting
  • Navigation by Smart Phone App

Price Excludes

  • Transport before and after tour
  • Flights
  • Travel Insurance
  • Hybrid Bike Rental
  • Race Bike Rental
  • E-Bike Rental
  • City Tax
Trip Info

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Arrival in Fano on the Adriatic coast

Relax in the beautiful Roman town of Fano with its nice beach

Day 2FANO – URBINO 39-42 miles 63 – 67 km up 1135-1395m.

Leave the wonderful views of the Adriatic Sea and enter the rolling hills. The magnificent medieval and renaissance town of Urbino awaits you full of architectural and artistic masterpieces. On your ride visit Fossombrone an ancient Roman town located in the Metauro valley. The ancient fortified medieval town is well worth spending time exploring and being just over half the distance ideal for a refreshment stop. Once in Urbino visit the  Duke of Urbino Palace, one of the most important Renaissance buildings in Italy. It has been a UNESCO World Heritage site since 1998.

Day 3URBINO – S. ANGELO IN VADO-SANSEPOLCRO 42 miles 68km up 1075m

Today continue cycling with views of towns and countryside to the beautiful medieval town of S. Angelo in Vado. S.Angelo in Vado has again Roman origins and like many such towns long historical ties to the church of which there are seven to be seen.  After some refreshments, you start the long climb to Bocca Trabaria pass at around 1050m but it is followed by a wonderful descent to the Upper Tiber Valley and finally into Sanselpolcro.

Day 4SANSEPOLCRO – CORTONA 42 miles 67km up 906m.

Optional loop day on the 10-night tour around Sansepolcro.
Today you have an epic ride across the pre-Apennines Mountains that separate the Upper Tiber Valley from the Chiana Valle. First, you leave Sansepolcro in a southerly direction which is mostly flat terrain before you head west and start climbing gently to 1000m. You will have great views as you descend to Cortona located just north of Lake Trasimeno and Chiana.

Day 5CORTONA – MONTEPULCIANO/PIENZA 28–44 miles, 45-70km up 555-1266m

Today you have a choice of 4 different rides depending if you are staying in Montepulciano or Pienza. Now you are in Tuscany where your cycle ride today is to Montepulciano one of the most beautiful hilltop towns of Italy known since old times for its prestigious Vino Nobile wine. Maybe your chance to taste some wine. Pienza is a town in Tuscany, Italy. The central Piazza Pio II is framed by 15th-century buildings like the Pienza Cathedral and Piccolomini Palace. The latter was Pope Pius II’s summer residence.

Day 6 MONTEPULCIANO/PIENZA – ROCCALBEGNA/SAN LORENZO 29-47 miles 49-75km up 1032-1501

Optional loop day on the 10-night tour around Montepulciano or Pienza.
A fantastic ride on the slopes of the ex-volcano Mt Amiata passing through olive groves, durum wheat fields to chestnut woods of Amiata. A must-stop today is Monticchiello located in the Val D’Orcia a UNESCO World Heritage Site for its natural beauty. Monticchiello is a tiny village not as well known, as its neighbours Montepulciano or Pienza but just as stunning to explore. 

Day 7ROCCALBEGNA/SAN LORENZO – SAVONA/PITIGLIANO 28-61 miles 48-97km up 657-1643m.

Today you will cycle the wonderful descent from the slopes of Mt Amiata to the remote Maremma, a rural area once the core of the Etruscan Territories.  You can also soak in the hot springs of Saturnia. Pitigliano really is quite stunning, carved out of volcanic stone it sits above the stunning green landscapes. The town is also locally known as “Little Jerusalem” thanks to its position close to Rome, where escaping Jews could find refuge. Pitigliano, as early as the 14th century, became an important haven for the Jews, and their numbers grew so much that they built a Temple in 1598.

Day 8SAVONA/PITIGLIANO – PORTO ERCOLE 48 miles, 77km up 891m.

Today a more relaxing easy ride in the flatlands of  Maremma to the scenic promontory of Mt Argentario in front of the Tyrrhenian Sea. Your tour is now complete, and you have cycled Italy coast to coast! Spend a relaxing afternoon on the beach or take a dip in the sea to bathe those tired legs!


Possible extension to 10 nights with loop rides Sansepolcro and Montepulciano/Pienza.


How to get there

Fly to Ancona, Bologna Forli or Bologna International airports and transfer by train to Fano

Book Now

2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
CTCIT1-8 (8 Nights) from £1547 Book Now
CTCIT1-10 (10 Nights) from £1877 Book Now
Tour Images
Cyclists on a Italian road