Central Italy is something not to be missed. Offering an abundance of medieval history, this Italian experience will take you back a step in time. If the stunning history captured in beautiful villages across Central Italy isn’t enough to get you to the heart of Italy, then enjoying some of the best food and wines Italy has to offer certainly will. Imagine overlooking beautiful tree lined rolling hills, sitting on a sandy beach or tasting Emilia Romagna’s famous cured meats and cheeses: this is just a slice of what this Italian tour has to offer, and because we do it on our bikes gives it a dimension no regular tour could offer!
Italy’s cultural identity, wine and cuisine offer a most genuine experience and will make for a most relaxing and enriching holiday. You won’t need to scratch your head with logistics and planning, just settle into each ride and let us guide you on your bike, amongst new friends, to beautiful riding destinations.
Dates:
24th May 2025 to 8th June 2025
From:
$7999.00 Twin Share
Rider Types on this Trip:
What's Included:
15 nights accommodation twin share at a selection of curated hotels
All Breakfasts
9 Dinners
All luggage transfers and transportation during your trip
2 Expert ride guides
Min 2 daily group ride options
Experienced mechanic
What's Not Included:
Airfare and transportation to and from the trip meeting/departing locations
Accommodation before and after the trip
Personal items purchased during the trip
Additional hotel expenses
Travel and personal insurance
Lunches & drinks
6 dinners are not included. We invite you to explore the local cuisine at your leisure.
Trip Highlights
Ride along quiet roads lined with olive trees and clear water beaches in the beautiful Italian landscape.
Tackle the winding ascents of central Italy.
Take a walking around San Marino, climb up to the castle with its magical high views of the surrounding area.
Relax and swim on the beaches of Rimini.
Visit the thermal springs of Castrocaro Terme.
People watch with a glass of wine in the vibrant town of Bologna.
Day 1 Perugia
Saturday 24/5/25
Arrival Day: Arrive in beautiful Perugia, check into your boutique hotel from 2pm in the centre of town. Take a stroll through the streets, have a coffee and watch the people before meeting up for welcome drinks and dinner.
Hotels
Included Meals
Dinner Only
Today's Ride
Distance 58km
Hotels
Included Meals
Breakfast Only
Day 2 Perugia
Sunday 25/5/25
Stage 1: Breakfast in your hotel, then a 9:00am roll out from the front of your hotel. We are riding across the valley to Assisi. A fun descent out of town, then across the flat valley before a steep climb into Assisi, then up to the castle for a stunning look at the surrounding area. Stop for coffee back down in the town square before heading back to Perugia. Spend the afternoon exploring the steep narrow streets or relax in one of the many bars with a drink and watch the Giro de Italia. There is no group dinner this evening, giving you the chance to explore or have a date night at one of the many restaurants in town.
Today's Ride
Distance 78km
Hotel
Included Meals
Breakfast and Dinner
Day 3 Gubbio
Monday 26/5/25
Stage 2: Breakfast in your hotel, bags to the front of the hotel by 8:30am. Rolling out at 9:00am from your hotel. Today we take the scenic route through the Umbrian hills to the gorgeous town of Gubbio. A very scenic ride with a few challenging hills before descending into Gubbio. Our hotel is just outside the city walls. After checking in take a stroll into town and check out the medieval shops before drinks and dinner back at our hotel.
Today's Ride Options
Distance 114km
Distance 50km
Hotel
Included Meals
Breakfast and Dinner
Day 4 Gubbio
Tuesday 27/5/25
Stage 3: Breakfast in your hotel, then a 9:00am roll out from the front of your hotel. Leaving Gubbio we tackle our first general climb, Madonna della Cima then climb up the back side of Monte Cusco to take in the breathtaking views while crossing into the next region of Marche before descending back into Umbria and a valley ride back to our hotel. Spend the afternoon exploring Gubbio. Take the chair lift to the top of the mountain overlooking our town. Sit down for a spritz to take in the view before drinks and dinner in our hotel.
Today's Ride Options
Distance 112km
Distance 67km
Hotel
Included Meals
Breakfast and Dinner
Day 5 Urbino
Wednesday 28/5/25
Stage 4: Breakfast in your hotel, bags to the front of the hotel by 8:30am. Rolling out at 9:00am from your hotel. Another lumpy ride leaving Umbria and into Marche. Magnificent quiet roads today up and down and over Monte Narone. Spectacular views and many quaint villages we ride through in our way to our destination of Urbino. After checking in to our hotel take a stroll through the towns ancient walls and historic centre. Famous for being a World Heritage Site notable for a remarkable historical legacy of independent Renaissance culture. Pre dinner drinks at our hotel before dinner in the hotels restaurant.
Today's Ride Options
Distance 98km
Distance 48km
Hotel
Included Meals
Breakfast Only
Day 6 Urbino
Thursday 29/5/25
Stage 5: Breakfast in your hotel, then a 9:00am roll out from the front of your hotel. Today we ride down to the coastal village of Pesaro. Coffee on the beach front and perhaps an early lunch before a lumpy ride back to Urbino passing through many little villages on the way. On return to our hotel enjoy resting or find bar in town to watch the final stages of the Giro de Italia. There is no group dinner this evening giving you the chance to explore or have a date night at one of the many restaurants in town.
Today's Ride Options
Distance 101km
Distance 59km
Hotel
Included Meals
Breakfast and Dinner
Day 7 San Marino
Friday 30/5/25
Stage 6: Breakfast in your hotel, bags to the front of the hotel by 8:30am. Rolling out at 9:00am from your hotel. Today we leave the region of Marche for a new country within Italy, San Marino. Majestic Castle Towers, Crown The Cliffs, standing watch over sweeping Vistas that reveal San Marino's breathtaking outlook. Departing Urbino we tackle rolling hills through many small villages on the way. Tackle the Passo Marco Pantini, stop for a coffee before our last climb into San Marino. After checking into our hotel it’s time to explore this small country and what it has to offer before drinks and dinner in our hotel.
Today's Ride
Distance 48km
Hotel
Included Meals
Breakfast Only
Day 8 San Marino
Saturday 31/5/25
Stage 7: Breakfast in your hotel, then a 9:00am roll out from the front of your hotel. Descending from the small country we move into the region of Emilia Romagna and through its rugged Regional Natural Park of Sasso Simone and Simoncello. With pleasant views and stunning scenery we descend down to the river and along to find one of so many places for lunch in Emilia Romagna famous for its food. A short ride back up to our hotel before relaxing and exploring then drinks and dinner at our hotel.
Day 9 Rimini
Sunday 1/6/25
Stage 8: Breakfast in your hotel, bags to the front of the hotel by 8:30am. Rolling out at 9:00am from your hotel. A short ride and almost all downhill to our holiday destination by the sea, Rimini. Park your bike and your on holidays. Enjoy the beach or stroll into town. But remember your on holidays so take it easy. There is no group dinner this evening giving you the chance to explore or have a date night at one of the many restaurants in town or along the beach front.
Day 10 Rimini
Monday 2/6/25
Stage 9: Breakfast in your hotel, then either take a day off the bike or come for a gentle spin along the beach with a coffee stop. 9:00am from the front of your hotel. Enjoy the rest of your day. There is no group dinner this evening giving you the chance to explore or have a date night at one of the many restaurants in town or along the beach front.
Day 11 Castrocaro Terme
Tuesday 3/6/25
Stage 10: Breakfast in your hotel, bags to the front of the hotel by 8:30am. Rolling out at 9:00am from your hotel. Today we head away from the coast and back into the hills passing though delightful villages through the heart of Emilia Romagna, with time to stop for a early coffee along the way. 5 climbs along the route, one may mistake we have been transported into the alps. Pristine narrow winding roads with little traffic zig zag us over the hills to our destination of Castrocaro Terme. After checking into our hotel it’s time to relax and enjoy this retreat before drinks and dinner in our hotel.
Today's Ride Options
Distance 120km
Distance 70km
Hotel
Included Meals
Breakfast and Dinner
Day 12 Castrocaro Terme
Wednesday 4/6/25
Stage 11: Breakfast in your hotel, then a 9:00am roll out from the front of your hotel. Enjoy the downhill start to the day as we coast down and through Forli and then the flat roads to Ravenna. A beautiful town just in from the coast. We take a sightseeing lap of the city before a coffee stop, then head back along the farm roads to our hotel. Spend the afternoon exploring the towns castle or the thermal springs in town or just relax and enjoy this retreat before drinks and dinner in our hotel.
Today's Ride
Distance 83km
Hotel
Included Meals
Breakfast and Dinner
Day 13 Bologna
Thursday 5/6/25
Stage 12: Breakfast in your hotel, bags to the front of the hotel by 8:30am. Rolling out at 9:00am from your hotel. With 3 days in Bologna we find a ride with a grand entrance into Bologna. Up and down all day with 7 climbs and a final descent into our destination. Coffee and lunch along the way. Everyone will have experienced Emilia Romagna’s wonderful scenery over the most scenic less traveled routes. After checking into our hotel it’s time to start exploring Bologna before drinks to celebrate, in our hotel and a short walk to dinner.
Today's Ride Options
Distance 124km
Distance 69km
Hotel
Included Meals
Breakfast and Dinner
Day 14 Bologna
Friday 6/6/25
Stage 13: Breakfast in your hotel, then a 9:00am roll out from the front of your hotel. With so much time needed to explore Bologna and so many hard days in the saddle behind us we have short loop ride around Bologna today. We pass many beautiful historical sights on the way out of town with a short climb up from the river that overlooks the city for a photo stop. Descending back into town we pass more historical sights and coffee in the piazza near our hotel. There is no group dinner this evening giving you the chance to explore or have a date night at one of the many restaurants in town.
Day 15 Bologna
Saturday 7/6/25
Stage 14: Breakfast in your hotel. Today stay in bed, get your walking shoes on to explore or join us for a short recovery ride at 9.00am and coffee along the way. (and at the finish). Pack our bikes up, find a nice place for lunch and spend the rest of the day exploring Bologna before drinks in our hotel and a short walk to our final dinner.
Today's Ride (Optional)
Distance 33km
Hotel
Included Meals
Breakfast and Dinner
Travel Details
How to Get There
TRAIN: from Bologna, FLY OUT OF: Rome or Milan
DEPARTING LOCATION: Bologna Hotel
DEPARTING TIME: Hotel Checkout is 11:00am
FLY INTO: Rome or Milan, TRAIN: to Perugia
MEETING LOCATION Pergugia Hotels
MEETING TIME: Hotel check in is 2:00pm
Departing
Getting to Rome or Milano Airport: The easiest and most convenient way is by train. Bologna station is a 10 min taxi ride from the hotel to the station. Take the fast train (1H:30Mins) from Bologna to Rome or Milan Centrale then change trains to the airport. (40Mins) Rome (50Mins) Milan
Arriving
Arriving in Rome or Milan you can transfer to Centrale via Airport train (40Mins) Rome (50Mins) Then take the fast train north or south to Perugia (1H:30Mins) On arrival at Perugia station a 10 min taxi ride you to your hotel.