Southern Tuscany Traveller Reviews

An incredible & unforgettable walk to some of the most beautiful hilltop walled towns in Tuscany. Sampling ldelicious ocal cuisine & wines along the way and staying at charming accomodation with beautiful views from our rooms.

Very quick to respond and always helpful

I did a seven day walking vacation through the hill towns of southern Tuscany. I walked from Siena to Montepulciano, passing through stunning towns and villages - like Montalcino, Pienza, and Montepulciano. I was a solo hiker who relied on On Foot to help me realize all the details of this magical trip. I travelled ridge tops, forded a few streams and rivers, enjoyed the smells, sights, and sounds of walking though vineyards full of the amazing Sangiovese grapes that go into the wines of the region. I arrived at my daily destination with plenty of time left to explore the culture and villages (in some cases UNESCO World Heritage designated). The food was crazy good, and so local - I'm sure I walked by much of it over the course of every day. The wine of the region tasted like crushed grapes and mineral soils of the towns smelled -- rich, spicy, lingering. All in all, a deeply intentional adventure in a landscape I've always longed to know better. I will be back!

I can't say enough positive things about On Foot - I booked this trip as a somewhat "last minute" idea. The whole team made it easy for me to undertake this journey. It was my first solo multi-day through-hike. The daily check in with Daniele (my On Foot local expert and contact in Italy), updates, and conversations were a real highlight of this trip - and truly contributed to piece-of-mind. And the contacts On Foot has with inn keepers, B&Bs, taxis, restaurants, cafes, helped make this a trip with real local heart. I would certainly use On Foot again.

Fabulous from start to finish (and everything in between)! Supported to put together a great 12 day holiday in Italy by the fantastic team at On Foot holidays. We spent 3 days walking in Cinque Terre (organized separately) before traveling by train to start our walking holiday in Southern Tuscany. We then spent a few days in Siena before returning home. Stunning countryside, great walking (even in the heat wave), lovely accommodation in beautiful hilltop towns. Everything went so smoothly! We loved exploring the hill top towns in the evening after completing our walk and chilling in the local bars and restaurants; ate some great food and everyone was so welcoming. The attention to detail by On Foot holidays and local support provided by our local contact Daniele was outstanding. This was our first ‘walking holiday’; I look forward to planning and booking our next one with On Foot holidays.

Fantastic from initial enquiry, through planning and resources provided to ensure we made the most of our holiday, to follow up post trip. Great, personalized service, which meant we could tailor our holiday to meet our needs. Very professional and personal in their approach to ensuring we could tailor our holiday to meet our needs. Excellent communication from start to finish.

We were on a four day all through the vineyards and hilltop towns in Southern Tuscany. We chose a rather hot time of year to do this but found that most of the hotels we stayed at had good sized outdoor pools. which we ere much appreciated to cool off in. On Foot arranged the hotels and luggage transfers so we didn't have a lot to carry. the scenery was stunning and the hilltop towns fascinating places to explore.

We found On Foot holidays a number of years ago through an article in the Times, since then we have been on five walking holidays across Europe with them which have all been excellent, They take great care to tailor the holiday to your needs and provide detailed information on the walks, they now have an App which saves on carrying paper and ensures you stay on the walking route as well as being informed on the places you pass through. We look forward to our next walking holiday

The Tuscany countryside come to life is just like the paintings we've seen only much better, of course. Going from hilltop town to hilltop town gave us such a scenic and intimate look at this uncrowded part of Italy. The background information provided by On Foot Holidays certainly enhanced our experience. Our luggage was transferred smoothly. The places we stayed were wonderful! The towns we went to each had something unique to offer and all were charming. Our walks not only took us into the beautiful, classic Tuscan countryside but sometimes we were in woods too. We went to abbeys, cathedrals and small chapels. It was all very diverse and interesting.

They personalize every individual trip and become like family. I have had contact with a number of staff and they all immediately address any questions/concerns I may have in addition to being friendly yet professional. The information provided is very comprehensive and we like the App along with the numerous hardcopy maps. I have referred many others to this company encouraging others to enjoy the benefits of walking holidays.

Excellent hiking trip walking through rolling hills of Tuscany and then climbing up to hilltop towns at the end of the day. The countryside is beautiful, even when it rained. Bring poles for sure as the clay soil in Tuscany is incredibly slippery in the rain. We stayed an extra night in Montalcino and 2 nights in Montepulciano. Highly recommend as there is so much to see around and in the towns.

This was our fourth trip with On Foot and they were excellent as usual. So responsive, professional and yet personal at the same time. We tell everyone to try On Foot.

We had an excellent walking holiday in Tuscany but had to make concessions due to previous months rain, muddy trails.

On Foot was a great tour operator- great downloaded maps/GPS program for use on iPhone. Excellent local contact for our hike. Great accommodations.

We undertook a self-guided walk through Southern Tuscany in September 2024. On Foot Holiday organized our accommodation, luggage transfers, and, where required, taxi transfers. This was a magnificent walk through gorgeous countryside, well within the capabilities of anyone who is reasonably fit. We enjoyed overnight accommodation in hilltop towns and, of course, savoured the delicious regional food and wines.

On Foot Holidays is a pleasure to work with. They are prompt and responsive, with an admirable attention to detail. Their walking packs are customized to one's travel plans, and contain a wealth of supporting information, including restaurant recommendations. I want particularly to mention their maps and walking directions, which are comprehensive and easy to follow. They have also recently developed a companion app that includes daily GPS-enabled topographical maps. This app provides an extra level of assurance that one is on the right track. And one more thing: they have engaged a local representative who is available for advice and assistance.

The description of the walk as an ‘amble’ was so inaccurate to be dangerous. We had terrible communication from the B&Bs and were even told “sorry I’m only the owner, I have nothing to do with the day to day dealings”. The ‘local’ tour guide was not sighted, and was worse than useless. Would not recommend at all.

No good.

A great experience walking through Tuscany. Very good accommodations, great food and well organized daily treks.

Onfoot holidays provided great support before the trip and while we didn't need much for them once we were on our way, when we did contact our local contact, the communication was flawless.