Bike Tour Reviews: Tuscan Wine Classic Pienza To Castellina Via Siena
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Self guided from EUR € 1720
Description:
Yes, there are hills, but your efforts on this tour will be rewarded with sunny Mediterranean ambiance and a spirited flair for hospitality. Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life. The route takes you…
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★★★★★ Claudia Lutke 7 days agoThe best way to have an immersive experience in Tuscany
The route, the bikes, the hotels. All received an A+ grade. Except the part of arriving in Pienza and leaving Castellina. The topic “How to get there”, part of a e-mail sent by you should be improved. The option TAXI from Chiusi train station doesn’t exist. No taxis there. There is only one bus/day to Pienza that departures in the morning. And we arrived in the afternoon. After asking four different people we realized that the only way available would be to take a bus - a city bus, not prepared for the transport of passengers + luggage - to Montepulciano and then find a way to arrive in Pienza. We thought that we could take a taxi there. But no taxis either. Fortunately, cel phones were charged and with internet access, so we contacted the local operator, explained the situation and they went to “rescue us”.
The same uncertainty happened by the time we left Castellina. We had 4 bags (it was a 20 days vacation trip, with different activities, including a meeting in between - with a “social” dressing code). It would require a considerable effort to carry the luggage until the bus stop, to take another city bus until Siena and then find a way to go to Florence (the place where we would continue the trip). The lovely cities that we visited in Tuscany are in fact villages. There are no taxi services overthere.
Again, the tour operator helped us passing the contact of a private driver who led us from Castellina to Florence.
My suggestion: include the transfer to the starting point and from the finish point in the “to do list” for the local operators when cities have such a limited options of transportation.- What was the date of your tour?
- Oct/Nov 2025
- How many tours have you completed?
- 5
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists
- Do you recommend this tour?
- Yes
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★★★★★ Michael Burkardt September 16, 2023
Beautiful Countryside
Our Bike Tour Company Cicloposse was exceptional, the best we ever had. There was not a single detail they missed, providing a booklet covering highlights for a given day of each town we'd pass through and as well as where to eat. We had a minor issue that was no fault of their own and the customer service was top notch. They're professional and knowledgeable. The only hiccup was a closed bridge that added a hour to our ride that day. Warning: unless you are a very strong rider get an E bike. Some climbs are miles long with a 14% grade.
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★★★★★ Amanda De Wet August 10, 2022
Best holiday ever!
Tuscany is beautiful, and it was amazing exploring by bike. We had the best time! Organization was excellent, local company was amazing and helpful, hotel accommodation was perfect - really cannot fault anything. Highly recommended!
- What was the date of your tour?
- July 2022
- How many tours have you completed?
- This was our first.
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists, Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ Rasp November 24, 2017
BEST honeymoon ever!
Well planned itinerary. Italian Guides were very friendly and knowledgeable and Set us up quickly and efficiently. Accompanying materials had great suggestions and option to do long or short ride every day was terrific.
- What was the date of your tour?
- October-nov
- How many tours have you completed?
- Several
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- Solo travelers, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ Snowball September 27, 2016
Best local bike company ever!
The local bike company were responsive to our needs and provided really excellent bikes. Accommodation was inspired.
- What was the date of your tour?
- July
- How many tours have you completed?
- 15
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- Solo travelers, First-time bike tourists, Families with teens
- Do you recommend this tour?
- Yes
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★★★★★ Rotsen June 21, 2016
A great way to embark on the endless search for a bad Tuscan wine.
The only thing that wasn't absolutely perfect on this trip was the weather. The bikes provided were new and light, 25c tires, Shimano 105 11sp compact group w/32T cog for easy climbing.
The route selection was wonderful, with a loop the first day to get acclimated and a loop the last day to provide options. The route cue sheets and maps included profiles and were spot-on so we hardly even bothered using the GPS routes they gave us to upload. We didn't have as much freedom to actually "tour" and stop at all of the sites as we usually do on tours due to the nearly constant threat of rain. Still we mostly avoided the rain until it arrived within last 5 or 6 kilometers on three of the days.
The upside was that we had more time in the towns we spent the nights, for wine and cheese tastings, and of course Gelato (If you ever come across Pear-Pecorino-Honey gelato don't be shy.) The hotel accommodations were terrific! Our luggage always made it there before we did. The breakfasts, the only meals included, were above par Continental with great coffee and, at the least, hard boiled eggs.. A number of times we ate dinner at the Hotel Restaurant. Following our arduous afternoon and evening searches for bad wine we kind of liked being close to our beds.
I am happy to admit that we failed utterly in our quest for a less-than-great Tuscan wine. We didn't bring any of the terrific Brunello's or Rosso's or Chianti's that we drank back, but did return home with 22kg of Pecorino Cheese most notably the Formaggio di Fosse. (My apologies to those who shuttled our baggage.) Someday soon we will return to continue our search, perhaps during a more dependably dry part of the year.
- What was the date of your tour?
- June 1
- How many tours have you completed?
- 8
- Difficulty (actual vs. expected)?
- As expected
- Who is this tour suitable for?
- First-time bike tourists, Families with teens
- Do you recommend this tour?
- Yes





