Welcome To Italy
Four
Regions
There is no better way to sample Italy at its best.
Cycle through
the country’s green heart and discover these four very special
regions in one single trip!
Discover
The Place
From the Adriatic coast to the rolling hills of central Italy,
this tour offers an 8-day cycling adventure through breathtaking
landscapes, rich history, and authentic Italian experiences.
Over six stages, guests stay in a different hotel each night,
setting off daily towards a new destination, while a support
minivan carries the luggage for a seamless journey.
Starting in Riccione, the route leads inland through
Marche, Umbria, and Tuscany, unveiling charming villages,
historic towns, and stunning countryside. Each day blends
sport, culture, and gastronomy, offering a perfect way to
experience the beauty and heritage of Italy in one unforgettable
trip.
Route Information
Duration: 8 days | 6 cycling days
Romagna, Marche, Umbria, Tuscany
First location: Riccione
Middle location: Perugia
Final location: Florence
Difficulty: Moderato
Schedule & Pricing
Total distance: 478 KM | 297 MI
Total elevation: 7875 M | 25,830 FT
Dates: On Demand
Price: 2900 €
Single occupancy: + 80 € for night
What's included
Discover the tour
day by day
Day 01
Transfer & Welcome
Airport transfer to Hotel Dory, our home base hotel in Riccione.
Meet your guides and the team. Our mechanic will do the final
touches on your rental bikes. Before dinner we will enjoy
welcome cocktails while talking about the cycling and culinary
adventure that lies ahead.
Day 2
Urbino Loop
We leave the sun-soaked paradise of the Adriatic coast and
cycle our way inland towards the Marche region, destination
Urbino. Urbino is a UNESCO World Heritage Site with a remarkable
historical legacy dating back to the Renaissance. It is the home
of Renaissance painter Raphael, and now, the University of Urbino
is situated in the historic city center.
On the way, we will pass many hilltop medieval towns and villages,
stopping for a delicious coffee along the way.
Our hotel for the night is right in the historic center of
Urbino. Before dinner, we will enjoy a stroll through the
narrow cobblestone streets where we can have an Aperol
spritz in one of the traditional bars around the main square.
BIKE: KM 45 - MI 28 | MT 1045 - FT 3444
Day 03
Gubbio
We will depart at 9 am after breakfast, and our destination is
glorious Gubbio in Umbria.
After a little detour to visit the canyon of Furlo with its
unique emerald green waters and Roman tunnel, we will arrive in
Gubbio in the afternoon
This distinctive medieval town on the slopes of Mt. Ingnio has a
rich history dating back to pre-Roman times. We’ll hear about
the famous Corsa Dei Ceri while tasting the local delicacy,
a handmade pasta dish with truffles, and sipping regional Rosso di
Montefalco wine. Buono!
BIKE: KM 90 - MI 55 | MT 1850 - FT 6070
Day 04
Perugia
Our day on the bike is entirely in the green heart of Italian Umbria.
After the initial flat section, we pedal through rolling hills with
breath-taking views towards ancient Assisi, the birthplace of St.
Francis and a UNESCO World Heritage Site.
After making the obligatory visit to the majestic Basilica of St. Francis,
we will be on our way to Perugia, the region’s capital city. We will settle
for the night amongst the centuries-old buildings of the walled historic
city center, enjoy a delicious dinner and admire the views down the valley.
BIKE: KM 81 - MI 1380 | MT - FT 4530
Day 05
Sansepolcro
We begin, as usual, at 9am, after a sumptuous breakfast, cycling
our way to the beautiful Lake Trazimeno.
We will pass quiet isolated
roads on our way to Sansepolcro, which lies on the border of three
regions and the upper reaches of the Tiber River. Now, we are in
Tuscany.
Tonight we will stay in a little family-run hotel which has a
wonderful, traditional high-end Italian restaurant and wine
cellar. We have been friends with this family for a long time,
and love sharing this experience with our guests.
BIKE: KM 95 - MI 59 | MT 1015 - FT 3330
Day 06
Siena
In the morning, as soon as we leave Sansepolcro, charming Anghiari
rises ahead on the horizon. Anghiari is a gorgeous hilltop town,
famous for the battle of 1440 between The Republic of Florence
and the Duchy of Milan. The battle inspired a planned fresco
by Leonardo Da Vinci known as the Lost Leonardo. Visiting Anghiari
leaves you with a deep appreciation for history as well as a sense of
eternal beauty.
We are now in the heart of The Apennine Mountains, approaching
Arezzo through the Passo della Libbia. We will take a well-deserved
coffee stop here, as the picturesque rolling hills will surely be
felt in our legs. But don’t worry! The minivan is right behind us for
any support you might need. We will take a break for a rural picnic
stop before Siena, and enjoy a cyclist’s lunch that we have prepared.
The last 30 km will be a rolling ride through vineyards and villages
before we arrive at Siena’s famous Piazza del Campo. Siena, we are
here!
BIKE: KM 105 - MI 65 | MT 1530 - FT 5020
Day 07
Florence
Chianti is quite possibly one of the best-known wines in the
world. Today, we are in the land where it takes its form, it
matures and is bottled to be exported around the world.
Our
route today meanders through the hills and vineyards, small
villages and castles of Chianti.
After a short stop in Castellina in Chianti, midway on the road
connecting Siena and Florence, we enter the grounds of the ruling
family of the region, the Medici.
During their centuries in power,
the Medici built beautiful country manors throughout the hills.
One of these manors will be our residence for the night. After we
check in, and before our final gala dinner in a typical trattoria
Fiorentina, there will be time to visit fabulous Florence.
BIKE: KM 62 - MI 38.5 | MT 1130 - FT 3707
Day 8
Goodbye
Time to say arrivederci and plan our next adventure.
What's included
7 Nights luxe accommodation (twin share), breakfasts, lunches, dinners, full guide and vehicle support, on-road snacks, daily pack, kit laundry service, one-time group airport transfer on arrival, departure and in between destinations.
What's not included
Flights, insurance, bike hire, alcoholic beverages,
coffee stops, personal hotel expenses, single room
occupancy supplement, city taxes.
Recommended Airports
Arrival: Bologna Marconi
Departure: Bologna Marconi
Photogallery
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Best Paradises
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Booking Trip
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Bike Hire
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e-RIDE 30
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Gravel e-RIDE 30
Official clothing
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Your Trip
Starts Here
Contact us to plan your next cycling tour or
hiking adventure and experience Italy like never before.
We’ll take care of creating a tailor made experience
for you, through breathtaking landscapes, authentic
villages, and unforgettable adventures, designed for fun,
relaxation, and discovering the very best of our country.
