General questions: Pienza, Montepulciano, Montalcino, San Quirico d'Orcia?


New member
The biking through Tuscany map itineraries were not viewable on the site!
It said view below but there was not anything to view.
Can this be fixed or can anyone help with this information?

Between April 4-9, my friend and I will be in Tuscany.
Most likely flying into Pisa and taking a bus from there.

We would like to visit everything, but with little time we have narrowed it down to the region around Siena and hopefully Chianti.

April 4: Arrive in Pisa late at night
Either bus to Siena, Pienza, or to florence
April 5: Considering a wine tasting tour to Chianti? If there are any from Seina or Pienza that would be preferable, the only ones I have found are out of Florence. Suggestions welcome!!
April 6: Stay somewhere in the beautiful Tuscan countryside
Looking for a B&B/something very Authentic, welcoming, and inexpensive.
Where is the best places to stay for little money and a good experience? I don't think hostels are an option for this which I'm happy about, but I can't afford to stay anywhere too expensive. Should we stay nearest a certain town? Some suggest Pienza, some Montepulciano, and some Siena. Would love to know where would be best in order to truly see Tuscany without feeling lost/confused/rushed, etc. Suggestions?

We would like to take this day and the 7th and 8th to explore the surrounding area, trying to avoid renting a car because it's too expensive. Is biking the way to go? What are the best routes? Where can we rent bikes? Is it hard to do this? I bike in Galway to school, but how far are the distances biking between each place? ANY information would be so lovely. We want a full Tuscan experience. Suggestions?

April 7: " "

April 8: " "

April 9: Bus from somewhere (Siena, Florence, etc.) to Ancona to catch a ferry to Croatia that evening!

Any help would be greatly appreciated. If I had more time to plan it would have been easier but it's a spur of the moment trip!

Cost-efficient is the most important thing for me at the moment, but I don't want to sacrifice anything so if something is truly worth doing please let me know!

All the best,


The Tuscan Expert ;-)
Staff member
Everything is impossible :)


First, if you arrive late into Pisa, stay the night there. Transportation options after a certain hour are limited. At most, trains to Florence are available but do you want that extra hour of train tacked on? Not knowing when you arrive, consider this before heading out of Pisa.

Valdorcia (where Pienza is located) is a beautiful area but hard to reach WITHOUT a car. From Pisa you can head to Siena by train, and if you don't want to rent a car, use that as your base to explore the area. There are buses to Pienza - check the Siena bus site for timetables

Is Galway hilly? All of Tuscany has hills so you do have to be in a very decent shape to plan to use that as your means of transportation... No matter where you go, you're climbing hills and then of course going back down. Most who bike in Tuscany use it as an experience itself, not as the means of transportation. Having said that, the hills to the south of Siena are some of the "softest" and rounded I have seen so it can definitely be pleasurable to see the area between Pienza, Montalcino, San Quirico on bike. We have not tried it yet (Stefano is the biker here and the one who could give you more info but he generally does Chianti as the area he bikes... He says it is challenging. The roads go from hilltop town to hilltop town so you're climbing 150 meters and back down continuously, that is what he says can get tiring.
how about looking for bike tours where they follow you along in case you need some help?

As far as accommodation goes, take a look at hotels, during this time of the season many have reduced their rates drastically:

It is hard to plan Tuscany - there are way too many things to do and too little time. My recommendation if budget is small is to stick to Siena and find a local agency there that can take you out to see Chianti and the Valdorcia. You can easily reach San Gimignano from Siena with bus 131.

Enjoy your time in Tuscany and come back another time to do what doesn't fit in this time!


New member
Re: Everything is impossible :)

Hello again! Thank you for the reply.

As it turns out, there were too many loose ends to not renting a car so we splurged and rented one. Unfortunately this means I'm on a smaller budget when I'm actually there! Very glad we did though, I think the trip will be a lot better because of it.

Now that those plans have changed I would love to know any budget recommendations for things to do that are actually worth doing!

This is the updated plan:
April 4: London-Pisa
  • Plane lands in Pisa at 9:50 pm.
  • Pick up rented car at airport.
  • Maybe make a quick pitstop by the tower of Pisa so my friend can see it, I already have. Either stay in Pisa, Florence, or Lucca. (Which of these 3 would you recommend the most? I figured if we wanted to see FLorence at all we should probably go ahead and drive there as soon as we can.)

April 5: Chianti Region
  • Either look around Florence a bit before heading to Chianti region or immediately head to Chianti region.
  • Chianti! - Wanting to taste some wines and all that, eat some tuscan food including OLIVES, see some lovely scenery! (Would love recommendations of course!)
  • Go to Greve and any other place worth seeing!
  • Drive south to Val d'Orcia area and stay the night.

April 6: Val d'Orcia
  • Spend the day driving around the Val d'Orcia area! (Pienza, San G, Montepulciano, Montalcino)
(Recommendations welcome again!)

April 7: Val d'Orcia/Siena
  • Same thing as the day before!
  • Drive to Siena
  • Stay the night in Siena with pre-booked B&B

April 8: Siena
(Recommendations welcome)

April 9: Siena-Ancona
  • Leave Siena to drive to Ancona!
  • Maybe stop somewhere along the way!

Thank you for helping!!



The Tuscan Expert ;-)
Staff member
Pisa, Florence, Val d'Orcia and Siena for sure!

Ciao Trace, missed your reply as I spent the rest of the weekend miserably sick... :(

The splurge on the car sounds very reasonable as it will make it easier to see the places you were planning in such a short time.

I think it would be a pity to fly into Pisa for your friend and not see it... You can of course pass by at night to only see it from the outside, but since you are on a budget, Pisa tends to be a little cheaper than Florence so you could spend your first night there, see the Leaning tower and other monuments both at night and in the morning and then head to Florence for the day. Spend the night there or nearby in Chianti.... Greve or Impruneta are good options.

For wines, visiting characteristic villages and great food, both Chianti and Val d'Orcia offer both.... So rather than spend an entire day in Chianti, I'd suggest driving through, having a nice lunch along the way and heading down to Valdorcia to be in the are by dinner time. Spend your day and a half in this area before heading up to Siena, there are plenty of beautiful villages and sights here to fill you up on Tuscan atmosphere.

For accommodation, both hotels and b&bs work well - use as your starting point to find something this last minute as far as availability goes.
For wine tasting, as you drive down and through the area you'll see wineries with signs offering tastings to the public. It is easiest to visit these as they won't require reservations.
For great food, go where locals go... Ask locals, they'll tell you their favorites. In Siena, several locals recommended "boccon del prete" which was good and we really like "trattoria di nonna Gina".

most of all, have fun!!