Hello, my name is David and my spouse and I want to plan a family experience for Spring 2027 in the Tuscany region of Italy. We think that we will have 4 adults including us, and 4 children aged 9-16. Early scenario for us is to rent a villa thru airbnb or VRBO, with pool, in or around Volterra and San Gimignano for the whole 10-days to use as a base to sleep and breakfast, for day trips or 2-day trips to surrounding locales such as Firenze, Sienna, Pienza, Montepulciano, Montalcino, and Piza. Looking for someone to share their itinerary for such an adventure. No budget restrictions and willing to stay overnight away from base to eliminate travel.
Option is to perhaps engage a cook for the morning breakfast for sure, and perhaps several evenings dinners back at base after touring all day. Also, want to experience dining at local restaurants. Feedback desired on hiring a driver with large van to accommodate whole family, for the whole duration of the stay. Will also consider using a tour service such as Viator for experienced guidance at all locations, and perhaps enjoy "skip-the-line" availability.
Hoping a Rick Steves community member has had such an experience and is willing to share the ininerary and highlight pitfalls and "must-see" attractions.
Thank you. David
Posted by
6607 posts
Feedback desired on hiring a driver with large van to accommodate
whole family, for the whole duration of the stay.
There are some drawback with this idea aside from cost. Do you think you will all want to do all of the same things or occasionally split up? Just renting two cars would be vastly easier, unless you are doing wine tasting, having some freedom might be nice, just something to consider.
Posted by
San Diego, California, USA
1927 posts
It sounds like you are looking for an agriturismo experience. A rural house with a working farm where some meals - especially breakfast - are provided. They also usually provide local experiences and recommendations for the area and things to do - wine tours, horseback riding etc. I would recommend you research this as a package rather than try and cobble it together by yourself.
Also be aware the Viator is consolidator of tours and services. So even if you use them for browsing dealing directly with these vendors cuts out the middleman and will generally provide a better experience.
I second the idea that having two cars be available is probably the way to go if you can swing two (or more) drivers within your group. Small Tuscan towns are not built for large vans and if one or two people take the van everyone else is stuck.
Tuscany is a very large area and so you are either further away from Volterra and Rada than you want to be or further away from Pienza, Montepulciano, and Montalcino than you want to be. The compromise area is probably someplace like Buonconvento which is ~1:30 from SG and about 30 minutes from Pienza. And the town itself offers bus and train service to Siena ~35 minutes as a bonus. And yes, this is the area I've got my eye on if I were to do the rural farmhouse in Tuscany experience again.
My $.02, rural Tuscany is as beautiful as promised, enjoy,
=Tod
Posted by
martinez, ca, usa
2919 posts
hey hey David
welcome to the forum
at least you're planning ahead. your 10 days is during high high season and will probably be HOT. don't just rely on airbnb/VRBO only.
the places you've mentioned will be busy as you can read other italy posts all mention the same towns/village with many bus & private van tours, personal car drivers, go early before they show up around 10am.
discovertuscany.com
check the "where to stay" with different types of places to stay in and where, what's offered within accomodation
chianti.com
check the headers that gives you lots of info and where you can all stay together with 8 of you, some have pools, serve breakfast, kid friendly. ask hosts about hiring a driver ($$$) or renting 2 cars between your gang. if you decide to rent a car, you will need an IDP (aaa.com/IDP) for each driver along with using your driver's license together. it is mandatory in italy. downfall with a car is parking, it's ugly in lots of places. train when possible
as hiredman mentions, viator is third party reseller. there are other sites that are better. you can scroll down and look for company doing activities & go direct to them
lots to think about, giving you other options, tuscany is a big area so you consult with group and decide what suits your fancy.
keeping asking questions, forum will give you good bad and ugly. best to do research, contented with your plans and not be stressed, have a great time
aloha