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Coast to Coast - L'Adriatico al Tirreno

Guided Road Bike Tour




9 days

Prices from

$3,115 P.P.

Coast to Coast - L'Adriatico al Tirreno

Guided Road Bike Tour




9 days

Prices from

$3,115 P.P.
Our coast to coast journey across Italy, from the Adriatic to the Tyrrhenian Sea has everything you could wish for; ever-changing landscapes, rolling hills, beautiful gorges and medieval hill-top towns. Passing through some of the country’s most beautiful regions including Umbria, Lazio and Tuscany this trip provides seven full days in the saddle fuelled by mouth-watering regional Italian cuisine and fine wine. What’s not to like?
We spend our first evening in Riccione, on the Adriatic coast, in the region of Emilia Romagna. The coastal roads and the hills that back on to them have turned Riccione and its neighbours into something of a cycling mecca, attracting thousands of amateur and professional riders each year, and we will spend our first day in the saddle exploring those roads and discovering exactly why.
After completing an Adriatic warm-up ride we set off on our journey properly, heading inland to the hills of Marche and the beautiful passes, valleys and gorges of the Apennine Mountains.
We push on into Umbria, the so-called Green Heart of Italy, renowned worldwide for its medieval hill towns, densely forested landscape and fine local cuisine and for good reason we will remain in this vicinity for three full days!
Leaving Umbria, we dip briefly into Lazio before exploring the roads of the Maremma in south-western Tuscany which lead us ultimately to the Tyrrhenian coast. Here we finally end our adventure by crossing the Tobolo di Feniglia, the narrow stretch of land connecting mainland Italy to the Argentario peninsula.




  • An epic coast to coast journey riding all the way from the Adriatic coast to the Tyrrhenian Sea
  • Cycling through the smallest republic in Europe, San Marino
  • Easing along the rolling Nove Colli hills, the routes of the famous Italian Gran Fondo
  • Visiting historical sites such as the Palazzo Ducale in Orvieto and San Francis Abbey in Assisi
  • Staying in quality accommodation, with fantastically warm hospitality
  • Riding to Gubbio and Assisi, UNESCO World Heritage sites

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Day 1
Arrival: Bologna / Riccione
Non Riding Day

Meet at Bologna Guglielmo Marconi Airport (BLQ) and transfer to the seaside resort of Riccione where we will build bikes and settle in time for dinner at one of the many local sea-front restaurants.

Day 2
Riccione Loop - Republic of San Marino
47 Miles / 75 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,200 Metres Approx.

We spend our first day on the bikes exploring a region of the Emilia Romagna hills which feature in the popular Grandfondo Nove Colli. Heading inland as soon as we leave town, it isn’t long before we are riding quiet country lanes and rolling through olive groves and vineyards.

We pass though Verucchio, marked by its prominent and impressive medieval castle before head into San Marino, Europe’s smallest republic where we stop for a bite to eat before descending back to sea-level and returning to Riccione for a second evening by the sea.

Day 3
Riccione to Urbino
40 Miles / 65 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,400 Metres Approx.

Having enjoyed yesterday’s warm up, today really marks the start of our journey. We begin the day heading south, hugging the coast for 25km before bidding a final farewell to the calm waters of the Adriatic when we reach the Parco Regionale del Monte Bartolo and turn sharply inland.

It is here that the coastal views and sandy beaches give way to rolling hills and valleys and before long we will leave Romagna and enter the region of Marche region and the the foothills of the Apennine Mountains. Our day ends with one final climb to Urbino, a town with a rich renaissance heritage and origins in the middle ages.

Day 4
Urbino to Gubbio
44 Miles / 71 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,200 Metres Approx.

Leaving Urbino and moving out of the Marche region, our stage builds gradually, becoming more mountainous as we progress into the densely wooded landscape for which Umbria is famous. It is a deeply sculpted terrain of steep forests dissected by steep craggy ravines created over aeons by the many streams and rivers. After crossing one of those rivers, the Candigliano, we begin a long and gentle climb on which we will spend much of the rest of the day enjoying the tranquillity of the mountain roads and views into the surrounding valleys.

After a scenic picnic lunch on a riverbank we drop down into a narrow valley which eventually leads us to the charming medieval town of Gubbio where we have time for a coffee and a little exploration of the narrow cobbled streets before saddling up to finish the day by riding a short distance to our lovely accommodation on the outskirts of town.

Day 5
Gubbio to Assisi
37 Miles / 60 Kms Approx.
  • Meals: Breakfast
  • Ascent: 750 Metres Approx.

We’ll be in no rush to leave our palatial surroundings and with our shortest and least challenging day ahead of us, there really is no need to hurry. But leave we must and once back on the bikes we will be amply rewarded as we travel deeper into the heart of Umbria.

There is only one significant climb today but it is an important one as it marks the natural watershed between the Adriatic and the Tyrrhenian and signals the halfway point of our journey. Once over the climb, the quiet country lanes continue to coax us onwards through yet more beautiful scenery as we make our way towards Assisi, UNESCO World Heritage site and the heart of a region that many consider to be the spiritual centre of Italy.

As we approach Assisi we’ll stop to admire the majestic San Francesco Abbey which dominates the hillside overlooking the town.

Day 6
Assisi to Orvieto
62 Miles / 100 Kms Approx.
  • Meals: Breakfast
  • Ascent: 1,450 Metres Approx.

The longest stage of our journey begins with 20 easy kilometres through the green valleys of Umbria as we meander through agricultural land to the pretty medieval village of Bevagna, where, if the mood takes us, we can stop for a coffee in the sunshine.

From here things get more interesting as the road begins to rise and fall repeatedly until we reach the hilltop town of Todi where we will break for lunch in the square overlooking the town’s cathedral or duomo.

The rollercoaster continues after lunch as we drop rapidly down to the banks of the Tevere river which we follow until it becomes the Lago di Corbrara. After crossing the dam at the western end of the lake we’ll the follow the road over two final little climbs all the way to beautiful Orvieto, famous for its dramatic gothic style cathedral. We’ll enjoy a well-deserved dinner in one of the many trattorias hidden away in the town’s narrow streets in a town renowned for its cuisine.

Day 7
Orvieto to Montemerano
53 Miles / 85 Kms Approx.
  • Meals: Breakfast, lunch
  • Ascent: 1,400 Metres Approx.

We have a change of terrain today as we leave Umbria to dip briefly into Lazio as we make our way ultimately to Tuscany. We say goodbye to green wooded mountains and hello to rolling hills and deep volcanic canyons and natural hot springs.

We begin the day with a lovely 15km climb through pristine countryside and a corresponding descent that takes us down to the shores of the idyllic Lago di Bolsena. We’ll stop for coffee at the lakeside from where the view of the lake’s almost perfectly circular shape reveals its volcanic origin.

Continuing along the lake for a further 10km we start to climb again and at the 40km mark we reach the highest point of the day before descending to the town of Pitigliano. Practically carved out of the rocks, the town is perched on a conspicuous limestone spur, and strikes an impressive pose against a beautiful volcanic backdrop. We’ll have lunch here and spend time exploring the maze of tiny streets, perhaps dropping into the small Jewish quarter, known locally as ‘Little Jerusalem’ complete with its ancient synagogue.

The final 30km are spent alternating between a landscape of craggy volcanic rock formations, deep valleys and thermal springs until we reach Montemerano, a town in the heart of Maremma renowned for the high quality of its local wine.

Day 8
Montemerano to Porto Ercole
44 Miles / 70 Kms Approx.
  • Meals: Breakfast
  • Ascent: 650 Metres Approx.

Early risers might want to pay a quick pre-breakfast visit to the local hot springs falls of Saturnia for an invigorating morning treat. The rest, we’ll see you in the breakfast room!

After a short descent as we leave Montemerano, the first part of our final stage climbs steadily for almost 25kms until we reach the town of Scansano where it is almost compulsory to stop for a while to take in the magnificent views of the Tuscan heartland.

A fantastic 30km descent through the ubiquitous vineyards and olive groves follows, eventually delivering us to the coast. Once at sea-level we ride across the narrow causeway connecting the mainland with peninsular of Agrigento before following the coastal road to our final destination of Porto Ercole, marking our arrival at the Tyrrhenian sea and the completion of our fantastic journey across one of the world’s most beautiful countries.

This evening we will celebrate in style style in a local trattoria and raise a glass as we reminisce about our wonderful adventure.

Day 9
Departure: Porto Ercole / Rome
Non Riding Day
  • Meals: Breakfast

Transfer to Rome Fiumicino (Leonardo da Vinci) Airport (FCO) for return or onward flights, or public transfer connections to the city for anyone choosing to extend their time in Rome.

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The Cycling


You will be travelling through 5 regions from north to south, moving from the lower Apennines with steeper gradients to the rolling hills of the Maremma. In all these regions your cycling experience will focus on riding through and visiting the unique towns and their architecture, some of which are UNESCO Heritage sites. In order to avoid the busy roads, we will take secondary roads through the countryside with varying quality of tarmac. As you travel across Italy, road conditions can vary depending on the geology of the region and relative ‘wealth‘, and road surfaces improve as you travel towards the Tyrrhenian Sea.


Road Cycling Grade

Grade 3: Moderate

45-60 miles / 70-95 kms per day

For riders with experience, good fitness & a decent level of skill

Some features that may be experienced more frequently in a higher grade tour

Most days include a couple of significant climbs

Some long days & some steep to very steep sections

Not for beginners

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

You’re definitely not a novice rider, you’re fit, you ride regularly at weekends, sometimes staying on the bike for much of the day, you love your bike! You also enjoy a challenge and if you haven’t already done so you’re keen to attempt a semi-serious to serious mountain pass or two. You’re as comfortable with the prospect of descending from the top of a col as you are with the idea of climbing it and you’re confident that you have the skills to do so safely. You’re not necessarily a “racer” but you can crank up the pace a little when it’s necessary and you don’t mind forgoing a coffee stop if the schedule demands it occasionally. You probably own and use clipless pedals. You have good control of your bike and can take a drink from a water bottle without having to unclip and put your feet on the ground. Whilst you find a full day in the saddle fulfilling you’re not obsessed and as much as you are looking forward to the riding on your holiday, you’re also looking forward to a little local culture and cuisine. Grade 3 would be a good option for you.

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

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Dates & Prices

Secure Your Holiday With A Deposit

Book now with a $250 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

Select a date to view prices and book
Start Date
End Date
Price p.p.
Start Date
Fully Booked
Return Date
9 days

Whats Included Tick

A) Accommodation (shared twin / double en-suite rooms)

B) Meals as per the itinerary (B=Breakfast, L=Lunch, D=Dinner)

C) Full tour service, including Skedaddle guides

D) Unless stated, at least one leader qualified in First Aid

E) Support vehicle and luggage transfers

F) Airport transfer on scheduled arrival day from Bologna airport (BLQ)

G) Airport transfer on scheduled departure day to Rome Fiumicino airport (FCO)

H) GPX files available on request

What's not Included Cross

A) Bike rental (available if required)

B) Flights and charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Single room (available if required)

E) Travel insurance

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to museums and other attractions en route

I) Airport transfers on days other than the scheduled arrival / departure days

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Private Departures

Private Departures

Are you keen to only travel with your family or friends? Struggling to find the right date? Well, we can organise a private departure for this tour and tailor aspects to suit your group's specific needs. Contact our friendly team and we'll help you turn your dream into reality.

The Essentials

Travel Options

Your tour starts in Riccione and finishes in Porto Santo Stefano.

Group airport transfers are included in the cost of your tour. Both the arrival transfer from Bologna airport (BLQ) and return transfer from Rome airport (FCO) will be co-ordinated with the group flight schedule.

We will provide you with details of suitable flight/arrival/departure schedules as flight timetables become available.

Please check with us before making any travel arrangements to ensure we have reached the minimum number required to guarantee your holiday and to make sure your arrangements fit with our scheduled transfers.

Please note If you make travel arrangements that fall outside of the scheduled transfer windows, there may be an additional charge for individual transfers.


The majority of our accommodation (shared twin or double rooms) will usually be en-suite in 3* hotels or guesthouses.

Bike Hire

Rental bikes will typically be a Giant Defy Advanced 2 or Giant Liv Avail Advanced 2 (for those preferring a women’s specific geometry) – or equivalent, with a carbon frame and hydraulic disc brakes.

These are great bikes with good quality components generally equipped with at least one bottle cage, a saddle bag and a small pump.

We can also include a helmet which should be requested at time of booking.

Please note that your bike will come with flat pedals as standard, so please do bring your own if you use clip-in pedals.

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