Tuscany trip and Itinerary help

bj henderson

New member
Your website is very informative and therefore I am emailing you for help.
We are 4 families (8 adults and 15 teenagers) who will be renting a large fabulous villa about 10 kilometers from Monteciano on August 8th. We will be in Tuscany for one week. We have rented cars but desperately need help (given our large group size) with planning day trips to the surrounding areas. As a minimum, we are interested in exploring small villages , visiting vineyards with wine-tasting tours (Brunello wine area, chianti and San Gimignano) lunch time dining at local tuscan eateries and perhaps perusing the local shops. Any suggestions would be appreciated


The Tuscan Expert ;-)
Staff member
you'll love the area around Monticiano

Ciao Barb and welcome to our Forum!

You'll be in a great area in Monticiano - we were there last October and loved that whole area from San Galgano to Paganico. The abbey was spectacular, and we highly recommend visiting Roccatederighi and Montemassi if you can.

If your group is into hiking a little bit, you can do the walk from Monticiano to the Abbey - it takes about an hour each way, all pretty flat. We also loved the short hike up to the ruins of the castle above Sassofortino through the chestnut forest. It really was a short hike and what remains of the castle is impressive; it was a nice stop near Roccatederighi.

With such a large group, you'll be fine with the outdoor visits to villages and shops but you definitely need to look into the meals and winery visits. For meals you might just need to reserve a day or two before, but for the wineries I suggest contacting before you arrive to set up a dedicated visit/tour.

Many of the restaurants we ate at in the area had large dining rooms so I don't think your group will have difficulty. Many are connected to "agriturismo" facilities - basically along main roads in the countryside and not necessarily in town. You'll see these as you move around, so keep track of them.

In Monticiano itself we ate at "Da Vestro" - it has a large dining room plus a large outdoor dining area. It is also a hotel if I remember correctly. For your first day it would be perfect since it will be nearby and you won't have to worry about finding a place to eat.
We ate there for lunch so we only had a pasta dish and dessert - our pici all'aglio and tagliatelle al cinghiale were both delicious :) Basically good local and Tuscan food. Found a site - http://www.davestro.it/ Tel. 0577 756618 / 756566. We remember also seeing a pizzeria in town which is another place you should try.

That day we had first tried to eat in Iesa, a few kilometers from Monticiano, at the Aia di Gino. Supposed to be a really good "slow food" restaurant with lots of home made dishes but it was closed! It must have been a Tuesday as I see it is their closing day here:
At the bottom of this page is a list of the restaurants and pizzerias in the area: http://www.sangalgano.org/ospitalita_alberghi_ville_agriturismo.htm

I am not sure of the total space available but we loved the Locanda nel Cassero in Civitella Marittima. http://www.locandanelcassero.com/ Tel. 0564 900680

In Roccatederighi try Garum and their "garum" pizza, really interesting flavors based on an "etruscan" sauce - Tel. 0564-567 445

As for wineries - there are so many it is hard to recommend one in particular. First, stick to San Gimignano and the Brunello and Montepulciano wine areas as they are closer so you'll have less driving to do. Having said that, start by looking at some of the places suggested here:
http://www.discovertuscany.com/forum/general-tourist-info/83-wineries-ourselves-rented-car.html or here http://www.discovertuscany.com/forum/general-tourist-info/123-any-ideas.html .

Do you have a particular wine/winery you like and want to visit? That is usually one good way to start, to look for an estate that produces a particular wine and visit them. Or you can consider contacting a tour guide and getting them to organize the visit for you. One example is this one: http://www.enjoyflorence.com/english/Wine_taste_Agriturism.htm which offers several tours, including one at the Castello di Verrazzano in Chianti which can include lunch or dinner.
Knowing the name of the estate, I found that you can book a tour directly: http://www.verrazzano.com/en/index.php?c=visiteguidate

For Brunello, two of the better known estates are Castello Banfi - you can read more at http://www.castellobanfi.com/tour/ - and Il Greppo - here is the link http://www.ilgreppo.it/wine_tasting.en.php

Hope all this information is useful, let us know if you want us to provide more suggestions for a particular place. I am sure you will all have a great time in the area you'll be in :)!

bj henderson

New member
Tuscany trip and itinerary help

Hi Lourdes,
Thank you so much for the information you posted for me . I look forward to exploring the web sites you suggested and I hope to gather more information to successfully plan for my Tuscany trip.
Again, I appreciate your input and help!
Barb :)