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The bike packing tour through Tuscany in September 2025 was my first bike packing tour that I didn’t undertake alone. My pedal pal Jörg joined me on the two-week round trip. In 13 stages, we rode towards the Adriatic Sea before returning to Florence via Perugia, Elba, and Siena.
We had ideal road bike weather. Only on the last stages did it get quite chilly in the evening at the stage towns.
Roundtrip starting in Florence
The number of flights has decreased significantly. As a result, the only option available to me was an early flight to Florence via Munich. However, our flights landed almost simultaneously, so we met already at the airport. There was a relatively new, fast, and inexpensive tram connection from the airport to the city center. From the tram stop, it was only a short walk to our accommodation in an old monastery.
After arriving, we dropped off our luggage and headed straight into the city for our first tour. We had reserved the rest of Saturday and all of Sunday for sightseeing in Florence before the round trip began on Monday morning.
It started!
The first few kilometers on the bike out of the city were tough. The heavy traffic, road closures, and interrupted bike paths didn’t make for a very enjoyable ride. That only came once we had finally left all that behind us. However, the first stage made up for it later with quiet roads along the Arno and a long, easy climb to over 900 meters, before it was basically all downhill to Arezzo.
Rain had actually been forecast for the first two days. However, we only got caught in the rain at the end of the first stage. Because it started raining heavily again in the evening after we arrived, the only thing we saw in Arezzo was a supermarket. Bad luck.
It was raining in San Marino at the start of the third stage, but it stopped after a few minutes. We didn’t have any more rain during the entire tour.
Apennines and Adriatic Sea
The next three stages took us from Arezzo to San Marino and further to Sassoferrato and Perugia. San Marino was the first highlight of the tour. A city-state housed on a single hill.
On surprisingly quiet roads, we continued our journey on the third day down to the Adriatic Sea. There, we rode a few kilometers close to the sea before the route took us back into the mountains to our destination for the day, Sassoferrato.
The fourth stage from Sassoferrato to Perugia was very beautiful. Highlights included the medieval towns of Gubbio and Assisi. Both are very different and both are very special.
We stayed in Perugia for two nights. The tour was still long, so we only went for a short ride on our rest day.
Onward to Elba
The next three stages took us from Perugia to Elba through the famous wine-growing regions of Tuscany via Montepulciano, Montalcino, and Grosseto. The towns were similar. They were all located on hills, the old towns were characterized by the Renaissance, and there were numerous tourists.
We took the ferry to Elba in the afternoon, so we stayed a total of three nights for two tours on Elba. It’s fun to be in a different place every day. But on a longer tour, it’s also nice to stay in one place for a while.
The first tour on Elba covered the west side, the second the east side. Both tours featured beautiful stretches along the sea, but also grueling climbs. For me, the west tour on Elba was the most beautiful stage of the entire tour.
Returning to Florence
On day 11, the last three-day block began with the ferry ride from Elba back to the mainland. From Piombino, we had to ride on main roads. This was an unpleasant stretch, which is why it took so long. After that, we continued on quieter roads, but the wind on the plain was blowing directly from the front. This didn’t change until we reached our destination in Volterra. When we finally reached the mountains, to make matters worse, we had to ride a very long and challenging gravel section. This stage wore me out and it took me a while to recover.
The reward came with the next stop, Siena. My favorite part of the trip. We enjoyed the wonderful atmosphere in Piazza del Campo. First after arriving in the sunshine, then again in the evening. By Siena at the latest, I was feeling fine again, and we took the longer route back to Florence for the last leg of our journey.
What remains of the bike packing tour through Tuscany?
We mastered the tour with ease over the two weeks. At the beginning, Jörg had to deal with numerous flat tires on his gravel bike, while I didn’t have a single flat on my road bike. Strange but lucky me.
We saw and experienced a lot on the tour. For me, Tuscany was rather unspectacular on a road bike. By car, the distances between the picturesque towns shrink, which distracts attention from the landscape. We also saw the postcard motifs, but with distances and a lot of landscape in between. It often seemed to me as if the wine-growing areas had shrunk considerably, which I found confirmed on the internet. The vineyard area fell from around 121,000 hectares in 1970 to around 60,000 to 61,000 hectares today.
And how was cycling?
Our experience with how drivers behave towards cyclists needs to be mentioned. As a rule, they overtook us at very close range. Fortunately, we rarely found ourselves on busy roads. Combined with the often poor condition of the road surface, this can be difficult. For example, you definitely always have to look behind you before swerving to avoid a pothole.
The stages of the bike packing tour through Tuscany
| start | destination | length | slop | |
|---|---|---|---|---|
| day 1 | Florenz | Arezzo | 112 km | 1.620 hm |
| day 2 | Arezzo | San Marino | 113 km | 1.950 hm |
| day 3 | San Marino | Sassoferrato | 145 km | 1.370 hm |
| day 4 | Sassoferrato | Perugia | 105 km | 1.900 hm |
| day 5 | Perugia | Ruhetagsrunde | 39,3 km | 650 hm |
| day 6 | Perugia | Montalcino | 116 km | 1.740 hm |
| day 7 | Montalcino | Grosseto | 109 km | 2.210 hm |
| day 8 | Grosseto | Portoferraio | 96,7 km | 840 hm |
| day 9 | Elba | Westseite | 85,5 km | 1.810 hm |
| day 10 | Elba | Ostseite | 85,7 km | 1.710 hm |
| day 11 | Portoferraio | Volterra | 110 km | 1.950 hm |
| day 12 | Volterra | Siena | 73,7 km | 1.250 hm |
| day 13 | Siena | Florenz | 107 km | 1.740 hm |
| total | 1.299 km | 20.720 hm |
You can find the exact route on Komoot in my collection “BikePacking durch die Toskana ab Florenz“.
