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Cycle Italy Coast to Coast
8 days
Italy - Trip code CUT

Cycle Italy Coast to Coast

On this road cycling trip we cross the breadth of Italy from the Adriatic to the Mediterranean, taking a beautifully scenic route passing through the regions of Le Marche, Umbria and Tuscany. Along the way we pass medieval towns, lakes, mountains, vineyards and Roman ruins. Each evening you can relax and reflect on the day's cycling over a glass of local wine and fine Italian cuisine.

Trip highlights

  • Coast to Coast - A bike ride from the Adriatic to the Mediterranean
  • Sense of achievement - Cross Italy on two wheels
  • Historic - Stay in medieval walled towns, see Siena and Roman ruins
  • Scenery - Enjoy nature with wonderful views along the ride
Accommodation grade:
Our standard, mid-range accommodation offers a good level of service, often with other amenities such as a restaurant, bar, garden or swimming pool. Generally rooms will be comfortable with en suite facilities.
Cycling grade:
Longer and more demanding for cyclists who enjoy hilly terrain with some challenging ascents. The routes require a good level of fitness including some non-technical, off-road riding.
Group Size:
10 - 16
Maximum group size ranges from between 6 to 20 people, depending on the type of trip, the transport and accommodation used and activities included. We rarely have groups that are smaller than five or six people and the average is 12 people plus an Explore leader.


Itineraries on some departure dates may differ, please select the itinerary that you wish to explore.

Day 1 - Trip starts in Bologna Airport; drive to Pesaro

We drive from Bologna Airport to our first hotel in Pesaro, a popular holiday destination in the Marche region with gold sand beaches on the Adriatic. The journey should take less than two hours and there will be time for an introductory briefing either before or after we settle into our rooms. Time to relax and unwind and enjoy our first evening meal (not included).

Accommodation: Hotel Imperial Sport(or similar)

Standard Hotel
Swimming pool available
Single room available
Meals Provided: None
Day 2 - Ride to the picturesque medieval walled town of Urbino

From Pesaro we ride through fields and great scenery as we rise up slowly from the coastal plains, through tiny villages, into the foothills with great views of the Adriatic coast and distant mountains. After a short break in the town of Fossombrone, the road begins to twist up and through a river valley. We end our ride in historic Urbino, a thriving cultural centre and university town whose fairytale skyline is visible for miles around. The ride today is fairly challenging as we climb up and away from the coast, on undulating terrain and there is one main climb to Urbino at the end of the day.

Our total cycling distance today is approximately 70 kilometres (total ascent 1050 metres).

Accommodation: Hotel Mamiani(or similar)

Standard Hotel
Swimming pool available
Single room available
Meals Provided: Breakfast
Day 3 - Cycle across the Apennine mountains into Umbria

After breakfast we leave Urbino on a beautiful ride that heads firstly to the Metauro Valley and the Furlo Gorge, an area of outstanding natural beauty. We then reach Piombico and the Apennine mountain range, passing close to Monte Nerone and Monte Catri. After Appecchio we cross into the region of Umbria, and continue our ride across beautiful countryside. Our final destination today is the medieval town of Gubbio. Perched on the slopes of Monte Ingino, Gubbio is the oldest town in Umbria and is worth an exploration before dinner.

Our total cycling distance today is approximately 72 kilometres (total ascent 1120 metres).

Accommodation: Hotel Gattapone(or similar)

Standard Hotel
Single room available
Meals Provided: Breakfast
Day 4 - Ride through Umbria to Tuscan hilltop town of Montepulciano

Today we have a classic ride through great Umbrian countryside with several ascents to wake your legs up and some fun downhills with great views. We descend firstly to the Roman Amphitheatre on the outskirts of town to view Gubbio's dramatic setting perched on the hillside. Then taking the road via Camporeggiano, we pass through tobacco growing areas as we make our way towards the town of Umbertide. After a rest stop here we cycle to Speddalicchio and Sorbello, before descending to the shores of Lake Trasimeno located on the borders of Umbria and Tuscany. After a relaxing break on the shores of the lake at Castiglione del Lago, we climb up again away from the lake and cross into Tuscany. At the end of today's ride we enjoy a slow climb to our accommodation in Montepulciano. After check in, we include a local wine tasting. The town is encircled by Renaissance era walls and fortifications. Within the walls the streets are crammed with wonderful Renaissance palazzi and churches.

Our total cycling distance today is approximately 87 kilometres (total ascent 1205 metres).

Accommodation: Albergo Marzocco(or similar)

Standard Hotel
Single room available
Meals Provided: Breakfast
Day 5 - A classic ride through Tuscan countryside to Siena

We start riding today through Montepulciano via the Piazza Grande. We then leave the town and descend to San Biaggio where our classic Tuscan journey really begins; a day of rolling hills, historic hilltop towns, cyprus-lined avenues and grand villas. We plan to have a coffee break in Pienza, depending on time, then continue by bike to San Quirico D'Orcia and San Giovanni D'asso which is renowned for its delicious truffles. Here we enter an area known as Le Crete or the Tuscan Badlands for a fantastic ride past Asciano town, cycling along an extremely panoramic road which leads us to the magnificent city of Siena and our accommodation for the night.

Our total cycling distance today is approximately 90 kilometres (total ascent 875 metres).

Accommodation: Hotel Colonna(or similar)

Standard Hotel
Swimming pool available
Single room available
Meals Provided: Breakfast
Day 6 - Free day in Siena. Optional Chianti Classico cycling

Today is free to spend at your leisure. You may wish to explore the delights of Siena with its Gothic and Renaissence architecture and medieval alleyways, or there is the option of taking an unsupported and self-guided cycle ride to explore the beautiful Chianti region. This ride will pass through the wooded hills of Chianti Classico, visiting the towns of Gaiole, Radda and Castellina. The centre of Siena is traffic-free, making it ideal to wander around on foot, soaking up the many intriguing sights. The Piazza is also used for a horse race twice a year - the famous Palio, where horses and their riders hurtle at a fast pace around the square to the delight of the crowds. Siena was once a rival to Florence in its power and commerce and controlled the trade routes between France and Rome, as well as the southern Tuscan wool industry.

Our optional total cycling distance today is approximately 65 kilometres (total ascent 950 metres).

Accommodation: Hotel Colonna(or similar)

Standard Hotel
Swimming pool available
Single room available
Meals Provided: Breakfast
Day 7 - Scenic cycle ride to the Mediterranean coast

Before leaving Siena we will cycle to the historic Piazza del Campo for a farewell group photo on this final day of riding. Then leave Siena behind and ride in the direction of Rosia, climbing up and over the pretty Montagnola Senese hills. One of our main stops this morning is in the Merse Valley at the ruined abbey of San Galgano which dates back to the 13th century. From here a lovely road leads us through forest to the impressive town of Massa Marittima, perched high up with impressive wide reaching views down to the coast. A rapid and exhillarating descent from here brings us down to the Mediterranean coastline and Follonica, our final destination, where we can dip our feet in the sea and celebrate the achievement of crossing the breadth of Italy!

Our total cycling distance today is approximately 95 kilometres (total ascent 810 metres).

Accommodation: Hotel Pineta(or similar)

Standard Hotel
Single room available
Meals Provided: Breakfast
Day 8 - Trip ends in Pisa Airport

We drive to Pisa Airport (1.5 hrs) where the trip ends. For those of you that have an afternoon or evening flight, there is the opportunity to travel into Pisa before returning to the airport for your flight. The airport has luggage storage facilities and regular, inexpensive shuttle buses into town. This is at your own expense and unaccompanied but the leader will be able to assist with information and what better way to finish a trip to Tuscany than visiting Pisa!

Meals Provided: Breakfast

Cycling information

General cycling information
On this tour we cycle 414 km over 5 days (an average of 83 km per day) with a further 65 km available. The terrain is generally undulating. We cycle mainly on quiet, minor tarmac roads with some short sections on main roads. A support vehicle accompanies the rides throughout the tour except on the rest day. We have graded the route as challenging.
Bike included
18, 20 or 22 gear Focus Culebro or Cayo road bikes with drop bar. Hybrid bikes are available upon request at time of booking.
Bike information
Your included bike is a 18, 20 or 22 gear Focus Culebro or Cayo road bike and will be the correct frame size for your height. Hybrid bikes are available upon request at time of booking. A small handle bar bag and a water bottle holder is provided. The bike is provided with flat pedals and has the facility to fit your own pedals (e.g. SPD or with cages) or saddle if you wish to bring them. A support vehicle accompanies the rides throughout the tour except on the optional ride and you can access your daypack throughout the day if you prefer not to wear it. We provide spare parts and take care of the day to day maintenance. All you need to bring is your own helmet.
Cycling grade

Why book this trip

Unlike many other operators, we include the hire of your bike in the overall cost of the holiday: you don't need to bring your own or pay extra to hire one locally. We also provide a support vehicle, spare parts and take care of day to day bike maintenance. All you need bring is your own helmet.

What's included?

Included meals
  • Breakfast: 7
  • Bus
  • Bicycle
Trip staff
  • Explore Tour Leader / Cycle guide
  • Driver(s)
  • 7 nights standard hotel
Award Winning Explore Leaders
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Price Guarantee Promise
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Airport Transfers
Read more
FairFX currency card
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Trip information

Country information



April/May and October/November are pleasantly warm. June/September are the hottest months. Showers are common in Autumn.

Time difference to GMT



2 Pin Round


Roman Catholic



Budgeting and packing

Optional activities

The following excursions and/or activities are usually available and may be arranged locally. Estimated costs are provided below for guidance only, are on a per person basis unless shown otherwise, and may depend on the number of participants. Prices quoted are correct as of the date these tour notes were originally issued but may change at any time due to currency fluctuations. Please note: These activities are booked and paid for direct with the supplier and do not form part of your Explore holiday contract.

Siena - Museo del l'Opera ticket GBP 10 for the Cathedral; L'opera Museum with panoramic terrace and Baptistry; 7 Euros to go up Torre Mangia in the Piazza del campo; Wednesday Market.


When cycling: quick drying cycle tops, padded cycle shorts, lightweight wind and water proof jacket and warmer breathable layers where local conditions require.
General: Pack layers of clothes essentially for mild or hot weather depending on the time of the year, but remember a warm fleece if travelling at the start or end of the season as the weather can be changeable.


If you are not bringing cycle shoes then try to bring stiff-soled shoes as these are better for cycling - transmitting your energy into the pedals more efficiently. This becomes more relevant and recommended the more demanding the grade and distances to cover. SPD cycle shoes are not well suited to tours that combine sightseeing with cycling.
Comfortable shoes, trainers, sandals or flip flops are useful when not on the bike.



Luggage: On tour

We recommend you bring a daypack and one main piece of luggage (total allowance: 44lb/20kg) which will be transported between hotels while you cycle. Check the bike details section to see if a pannier or handlebar bag is provided on the bike.


On all Explore cycle holidays we strongly recommend you bring along and wear your cycle helmet. In case of an accident resulting in personal injury, certain insurance policies are invalidated in cases where a helmet was not being worn. Cycle glasses to protect against dust, pollen and the sun, padded cycle gloves and a water bottle or water delivery system (e.g. camelback or platypus) are also useful. You may choose to bring your own gel seat cover for added comfort. If a handle bar bag or pannier is not provided (check bike details) then you may like to bring a small rucksack to wear while cycling. Other items to consider bringing are a sunhat and sun cream, torch, earplugs and insect repellent. Please carry some or all of your cycling equipment e.g. helmet as part of your hand luggage.


Explore leader
At your discretion you might also consider tipping your Tour Leader in appreciation of the efficiency and service you receive.
Local crew
Although entirely voluntary, tipping is a recognized part of life in this region of the world. Some local staff will look to members of the group for personal recognition of particular services provided. In order to make things easier for you, the Tour Leaders may organise a group's tips kitty and if this is the case, they will account for it throughout the tour.
Country Information


Food and drink

The costs for meals may vary depending upon location, type of restaurant and number of courses eaten and so the prices given are an average guide. Local restaurants located off the beaten track may be less expensive, whereas an upmarket restaurant located in the centre of a major city may charge more.

Lunch price
£5.00 - 10.00
Dinner price
£15.00 - 20.00
Beer price
£2.00 - 4.00
Water price
£1.00 - 2.00
Foreign Exchange
Local currency
Recommended Currency For Exchange
Where To Exchange
We recommend that you change any currency into Euros prior to arrival. Bureau de Change are generally only found in major cities and large airports.
ATM Availability
Major towns.
Credit Card Acceptance
Larger hotels and restaurants.
Travellers Cheques
Only in major towns. Please note, the exchange rate for cash and Travellers Cheques is poor.

Transport, Accommodation & Meals

Transport Information

Bus, Bicycle

Accommodation notes

Booking a Single Room

All of our group tours are planned and operated on a twin-share basis, meaning that the standard cost is based either on individual travellers sharing accommodation with another group member of the same sex, or people who book together sharing accommodation. Please refer to the tour notes where the single room option availability is detailed on a night by night basis for this tour, and the price for the available nights is detailed on the dates & prices tab by departure date. For Self-Guided trips the Single Room supplement offers the option of a single room each and is charged per person. The Single Room supplement also applies to the third person in a party of three that will be accommodated in a single room.

Standard - Our mid-range accommodation offers a good level of service often with other amenities such as a restaurant, bar, garden or swimming pool. Generally rooms will be comfortable with en-suite facilities.

Essential Information

FCO Advice

We strongly recommend that you check your government's travel advisory for up-to-date information and advice about your destination: safety and security, entry requirements, health, local laws and customs. For UK Foreign and Commonwealth Office advice click here.

For more information from Explore about travel advice, click here

Under 18 immigration guidance

Please note that some countries require proof of parental consent when travelling overseas with under 18s. Please check requirements with the relevant embassy or consular office well in advance of travel if this applies to your party.

Price Guarantee

Once your booking has been confirmed we guarantee the price will not increase, whatever the circumstances. Before booking please ensure you have read our important tour pricing information.Booking Conditions

Visa and Passport Information

Italy: Visas are not required by UK, E.U nationals, Australian, New Zealand, US and Canadian citizens. Other nationalities should consult their local embassy or consular office.

You should confirm all visa related questions with the relevant Embassy prior to departure.

If you do require assistance in obtaining a visa then you may consider applying through Explore's recommended visa service in the UK, Travcour. See to download the relevant visa application for your trip, if applicable (UK citizens only), along with details of how to apply for your visa through Travcour. The Team at Travcour will be happy to answer specific questions relating to visa applications, please call them directly on 0208 5431846.

It is your responsibility to ensure that you are in possession of a full passport, with the correct validity for your chosen destination.

Booking conditions

Before booking your Explore trip, please ensure that you read both our Essential Information and Booking Conditions.


Find out more about Trip Transfer Terms and Conditions before you book.

Booking a land only package with Explore

Customers who have chosen to book on the ‘Land Only’ arrangements of our tour, please ensure that you have checked your tour specific ‘Joining Instructions’ prior to booking your own travel arrangements. Your joining instructions can be found below in the dates and prices information. 

You may also be eligible for the Free Explore Transfer.

Joining Tour Abroad

Customers booked on the ‘Land Only’ arrangements will now receive a Free Transfer, provided you arrive and depart on the tour only itinerary start and end dates. The transfers will be from the Explore designated airport or train station to the joining point of your tour, and then back from the ending point to the designated airport or train station. The exception to this rule is customers who are booked on a tour where the joining and ending point is at the designated airport or train station.  

Free transfers are not available for Self-Guided, Polar, Tailormade or Tours for Churches customers.

If you are not eligible for the Free Transfer then you will need to make your own way through to the joining and ending point. On a majority of our tours Explore will be able to provide a private transfer at an additional cost. Please ask for a quote at the time of booking.  

For more information regarding the Explore Free Transfer click here


It is a condition of booking with Explore that you have adequate valid travel insurance. It is your responsibility to arrange appropriate travel insurance and ensure you have read and understood the full terms and conditions of your travel insurance policy to ensure that you are covered for all activities you intend to undertake whilst on the tour, including all optional activities. Your Insurance Policy must fully cover you for medical expenses and emergency repatriation to your home country. Please ensure your policy includes medical emergency helicopter evacuation in the event of illness or injury and covers the entire duration of your holiday. If you are trekking at altitude please ensure that there is no upper altitude limit which may limit or exclude cover for your trip. The cost of many of our Polar Voyages will exceed the capped amount covered by standard insurance premiums and you will be required to pay an additional premium to cover the full value of your trip. Please ensure that you are covered for the full amount of your holiday cost, as insufficient cover could invalidate a claim under the policy. Medical and repatriation insurance cover is not mandatory for UK residents who are travelling on trips within the United Kingdom.
Read more information about what travel insurance is required.

Flight information

Explore offers a wide range of flexible flying options to make joining and leaving our trips easy. Read more about them here.

Flight Information

You are able to book this tour on a 'land only' basis or as a ‘flight inclusive’ package. Your flight inclusive package will be fully protected by the Civil Aviation Authority (CAA) ATOL protection scheme.


Booking a flight inclusive package with Explore

We have a good selection of flights not only from London but from many regional airports around the UK allowing us to compare fares between scheduled carriers as well as low cost and charter airlines. Our dedicated flights team will match the best flight options to your arrival and departure airport.

On our website we display a UK flight inclusive package guide price which is generally based on a London departure. To avoid paying supplements or to secure your preferred flight option, we recommend booking as early as possible, especially for peak travel dates.



Nothing required. Tetanus recommended. Please check the latest requirements with your travel clinic or doctor prior to departure. The above is not an exhaustive list. Further information regarding vaccinations and travel health advice can be found by following the NHS and NaTHNaC links at Explore Travel Health and from your local healthcare provider. Visa and vaccination requirements are subject to change and should be confirmed by you before travelling.

Dates, prices and booking

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