Iconic Cities, Spectacular Landscapes & Stunning Hilltop Towns from Florence to Rome

There’s something special about riding a bicycle in Italy. It’s a country that rewards the two-wheeled traveller with its stunning landscapes, historic towns, friendly people, and delicious food and wine. Away from the frenetic cities, cycling along countryside roads, you get a real feel for la dolce vita. It’s the number one destination for Freedom Treks customers, and I’m inclined to agree with them.

I travelled the length of Italy by bike in 2017, from Puglia in the south to the Alps in the north, but I hadn’t been back since. For Craig, this was his first experience of a full Freedom Treks tour. It turned out to be a fantastic week for us both, learning more about this part of central Italy and experiencing the day-to-day of the tour itself. Read on for our trip report, you might discover that Florence to Rome could be perfect for your next cycling holiday!

We flew to Florence Airport with Vueling from Gatwick. The airport is linked to the city’s tram line which makes the transfer to the hotel very straightforward. Pisa Airport is also a good option, as you can take the train from there into central Florence.

We arrived early in the afternoon so, after checking in at our hotel, we set out to explore the city. We’d both visited before, but Florence is a city that merits a second (or even a third!) visit. There’s always something more to see, a new alleyway to wander down, a different angle of the Duomo to view or an undiscovered cafe or restaurant. Speaking of which, it just so happened to be ‘International Coffee Day’ (the first of a couple of serendipitous dates that coincided with our trip), so we made sure to sample a few local cafes. Always an espresso, always standing at the counter, of course.

We drifted through the piazzas, past museums and galleries, then across the Ponte Vecchio taking in the sights and sounds of the city on a bustling Saturday afternoon. We ended up on the south bank of the Arno River at Piazzale Michelangelo, sat on a terrace overlooking the city for the first of what became a traditional late afternoon sundowner. As we enjoyed the views, we took a moment to look through the route booklet and tour app to plan ahead and understand a little more about the places we’d be seeing and cycling through in the coming days.

The first day of cycling starts with a transfer from Florence to Arezzo, which takes around an hour. (Depending on numbers, this will either be by train or minibus). We had a quick bike handover outside Arezzo Station, giving us a chance to check that our hybrid bikes were set up comfortably for our heights, and then we hit the road (after a coffee, naturally).

The route quickly took us out of town and into the countryside, mostly made up of farms and olive groves. To start with, the scenery was nothing spectacular, but it was a nice way to get used to the bikes on quiet roads with a few undulations over gentle hills.

Almost immediately as we crossed the border from Tuscany into Umbria, the overcast skies made way for sunshine and we started a mellow climb up to a ridge where we caught sight of Lake Trasimeno, Italy’s fourth largest.

We knew (thanks to supplied route information) that there wouldn’t be many places to stop for drinks or lunch for the first part of the day’s ride. It’s definitely worth packing a few snacks for the morning and waiting until you reach La Puntabella for a lunch stop. After a great lunch sat on deck chairs on the terrace overlooking the lake, we were glad that the last few kilometres to Passignano were mostly downhill!

Watch our Day 2 highlights on Instagram.

With a relatively short ride to Perugia, we spent the morning wandering around Passignano and visiting Isola Maggiore, a small island a couple of kilometres off Passignano. The hotel was happy for us to leave our bikes, and we left our luggage ready for collection before hopping aboard the small ferry which makes the crossing to the island. There’s a tiny settlement and various churches dotted around the island, linked by well-marked footpaths, which made for an interesting side trip.

Back on the bikes, the first half of the ride was around the shoreline before a climb away from the lake into the hills to the east. After our morning walk around Isola Maggiore and an hour or so on the bikes, we were ready for lunch when we reached Magione. A pizza and a small glass of wine sat overlooking the hills was a welcome stop.

It wasn’t much further to Perugia, Umbria’s capital, which sits high on a hilltop keeping a watchful eye over the province. The ride up to the historic city centre got the legs working, but it was an exciting arrival. The road snaked its way around the outside of the city walls, then we passed through a grand arched gateway and cycled straight into the main square in the shadow of the gothic cathedral. Our hotel was right in the centre, so we left our bikes and went to enjoy a post-ride negroni sat outside Bar Duomo in the main square, a perfect suntrap which kept the late afternoon sun until it dipped below the crenellated roofline of Palazzo dei Priori.

Watch our Day 3 highlights on Instagram.

Before setting off from Perugia, we cycled via the Carducci Gardens and a viewpoint looking southeast over the Assisi Valley. A spectacular view awaited us, the morning mist hanging in the valley and the sun rising into a clear blue sky. In the distance we could see Assisi, the day’s destination, with the white stone of its cathedral and old town glistening in the sun at the foot of Mount Subiaso. It so happened that today was the 4th of October, the Feast Day of St Francis of Assisi. Incredible planning by Team Freedom Treks, or pure fluke? You decide, but what better day to visit the historic, cultural and religious centre on our own little two-wheeled pilgrimage?

It was another short day, which felt even shorter as it started with a long swooping downhill from Perugia. The route took us on country roads on the flat valley floor, across a couple of rivers on old stone bridges, quickly bringing us closer to Assisi. We stopped at the lower part of town to take a look at Basilica di Santa Maria Degli Angeli, a domed church with intricate facades of white stone and marble, and then continued on for the last few kilometres uphill to Assisi itself.

The police roadblocks and helicopters overhead told us that they take St Francis Day pretty seriously. It turns out the President of Italy was visiting, and the Pope had been there a few days previously. Luckily for us, we were waved through the barriers on our bikes, so it meant quiet and traffic-free roads for the switchbacks up to our centrally located hotel.

The town itself was bustling with visitors from all over the world and the cobbled streets were lined with market stalls. After a leisurely wander through the streets and our traditional late afternoon refreshments, we ended up in front of the cathedral where we saw one of the most spectacular sunsets imaginable. Whether or not you believe in the religious significance of the day and the place, there was something magical in the sky that evening.

Watch our Day 4 highlights on Instagram.

This was a longer day which also started with a long downhill that was so much fun, we sailed past a turning on the route! Luckily, the navigation app let us know straight away that we’d gone wrong, so a quick U-turn put us back on track. We cycled on through the wide valley, between the many walled hill towns that the area is famous for. 

Our first coffee stop was Spello, the second, Bevagna. Both in picturesque town squares at cafes full of locals chatting and going about their day. The caffeine boost was welcome as we’d planned a detour to visit Montefalco, the ‘balcony of Umbria’, a centre for winegrowing in the region and one of my favourite towns in Italy. The climb added a good amount of vertical to our route, but the views were well worth it as we cycled and especially once we reached the top. The wine tasting and pizza were an added bonus!

A quick downhill took us back to the recommended route which followed a scenic cycle path alongside a river all the way to Spoleto. With the longer ride and additional detour, we arrived quite late in the afternoon, but we still had time to check out Ponte delle Torri, an impressive viaduct spanning 230 metres between two hillsides, 80 metres above the valley below. It’s currently closed for renovation and reinforcement so it’s not possible to walk across, but there’s a viewpoint and gelateria there, which we took full advantage of.

Watch our Day 5 highlights on Instagram.

South of Spoleto, the valley narrows and we were into the hills. There weren’t many towns or villages along the way, and the first hour or two of the day was spent gradually gaining altitude, stopping occasionally to look back at the views behind us, stretching over Spoleto and Assisi to Perugia in the far distance.

Once we reached the top, we were rewarded with a long, winding downhill which seemed to go on forever. We couldn’t wipe the smiles from our faces and, as we coasted to a stop at the bottom, we realised we hadn’t actually taken any photos of the spectacular gorge we had just ridden through. We’d enjoyed it so much that we decided to cycle back up and do it again. It was that good.

We bypassed Terni on a short section of busier suburban road. This tour is rated Moderate, partly for the undulating hills and also because much of it is on roads rather than cycle paths. It’s comfortable for experienced cyclists though and, as ever, the Italian drivers are very respectful of bikes and their road space.

Umbria is said to be the ‘Heart of Italy’ and the day’s ride finishes in Narni, the geographic centre of the country. It was also C.S. Lewis’ inspiration in naming the fictional land of Narnia in The Lion, the Witch and the Wardrobe. He never visited, but liked the sound of the name apparently.

After an uphill ride into town to finish a long day in the saddle, we really enjoyed a paddle and a quick dip in a crystal clear river next to the ruins of the Bridge of Augustus, a stone aqueduct destroyed by an earthquake in 847 AD.

Watch our Day 6 highlights on Instagram.

We set off early for the final day on our bikes as we had a train to catch in the early afternoon which would take us into Rome. We followed the valley through the Sabine mountains and past Calvi on roads lined with vineyards.

We covered the distance quickly with only a quick coffee stop interrupting our flow. As the distance ticked down, we realised we were making very good time, and could probably treat ourselves to a well-deserved Friday beer. The tiny hill town of Rocchette gave us the perfect venue, where we sat outside on a balcony enjoying our celebratory refreshments.

From there, the hills gave way to another wide valley, stretching away to the south towards Rome. We finished the ride with a long downhill to Poggio Mirteto where we said goodbye to our bikes and boarded a high-speed train into the city.

Watch our Day 7 highlights on Instagram.

As the saying goes, Rome wasn’t seen in a day. Or something like that, anyway. But with just a few hours to spare and an early flight the next morning, we were going to give it our best shot! 

Neither of us had visited before, so we got the map out while we were on the train and plotted a rough route around the famous sites. From our hotel, we set off on foot and started ticking off the highlights, starting with the Colosseum and Forum, then on to the Altare della Patria. From there, we had to visit the Trevi Fountain, which we could just about see through the crowds while we had an energy-boosting gelato. Up next the Pantheon and the Piazza Navona where we paused our final (and most expensive) negroni of the trip.

As the light started fading, we reached the River Tiber in time to see another gorgeous sunset behind the Vatican. We finished the loop with the Spanish Steps en route to dinner. Once we were back at the hotel, we’d covered over 15 km in a few hours. We didn’t see everything, and really only scratched the surface of what we did see, but we packed in as much as we could with our limited time in Rome and it was a fun evening to round off a wonderful trip.

Watch our Rome highlights on Instagram.

The food on this trip was amazing, so it deserves its own section! As you’d expect in Italy, we ate very well. We made sure to sample all the classic pastas, pizzas and risottos as well as some regional specialities like Florentine steak in Florence and truffles and wild boar in Umbria. Craig is vegan, so in smaller towns we sometimes had to try a few restaurants to find one that could accommodate, but in other places we found some really excellent vegan options.

With the daily coffee stops, along with a few extra pastries and ice creams, it was a good thing we were cycling every day to burn off the extra calories!

1. We flew into Florence and out of Rome to minimise airport transfers. Flying into Pisa is also a possibility. 
2. You don’t get much time in Florence or Rome, so it’s worth adding an extra night at either end to see more of each city without having to dash between the sites.
3. The transfer from Florence on day 2 will either be by rail or road. Your info pack will be waiting for you on arrival and will detail this. Either way, you’ll be setting off promptly, so it’s a good idea to have bags packed and be dressed in cycling gear when you come down for breakfast.
4. The navigation app is excellent, and you’ll be able to download this and the routes to your smartphone in advance. We recommend bringing a handlebar attachment for your phone and a battery pack.
5. E-bikes are a good option on this tour if you’d like some extra help up the hills.
6. There are a few stretches on this tour where you won’t pass cafes or shops for a while. These are pointed out in the route information, so we always recommend looking at the days ahead and planning for picnics and snacks en route.
7. At the end of the ride when you take the train from Poggio Mirteto to Rome, you will handover your bikes and also your panniers. Remember to bring a backpack or light bag with you on that day to transfer your belongings into. Don’t forget to have your train ticket with you (which you’ll receive in your info pack on arrival.)
8. If you have the time, why not try our full Venice to Rome tour? It’s a 14 night trip, where you’ll first cycle from Venice to Florence, then you’ll follow this route from Florence to Rome for the second week.