lots to do... maybe you should stay in Tuscany on this trip!
Ciao Lee,
Wow lots of questions so let's see how to tackle them.... first, considering you have two weeks, you will have a chance to see each place you go to without being in a hurry.
The places we suggest for a first time visit to Tuscany are all listed here, so start by getting an idea of places to visit and see from here:
7 day itinerary in Tuscany.
1.
rental cars vs train - you're going to have to run some test reservations on both a car rental site (try Auto Europe's
car rental search engine , it searches across various car rental companies in the same way some other aggregators do
and once you reserve tells you which agency to go to) as well as
trenitalia.com to see cost of train tickets.... regardless of your choice of whether to rent in Rome or in Florence, keep in mind that a car is definitely a necessity to move around Tuscany......... so if you're renting, you might just do it from the start (I see one way train ticket from Rome to Florence costs 30-45 euro per person). So even two cars might be cheaper than rental+train.
2. The main sights in
Venice are on the islands -- so you have to drive to Venice Mestre (land) and park there and then take the train (less than 5 min ride) into the island or a boat shuttle.
3.
Accommodation choices: there are many villas that offer B&B service (some offer just breakfast, others will also offer dinner if reserved) but keep in mind these are the ones that set up as a B&B and not as apartments (these generally are "self-catering") or as a villa offered as a whole. Off the top of my head, I do know of two that would be perfect:
Villa Dianella - has 4 bedrooms so perfect for your group, and set up as a B&B so offers breakfast. As they offer cooking classes for guests, there is a kitchen available so contact them directly and ask whether upon request they can cook for your group. They are located near Vinci, pretty centrally located in Tuscany which would make it a good base for two entire weeks.
Tenuta Quadrifoglio - another great possibility, as it offers apartments as well as rooms and breakfast is also available to guests staying in the apartments - also very centrally located near Gambassi Terme and has chefs on hand for lunches and dinners (make sure to contact them and ask)
4.
itinerary: this is very subjective and depends on what your group wants to do, your likes and interests... you ask whether there are other places aside from Venice to add to the trip but Venice is already not very close to Tuscany and is a over a 3 hour drive from Florence. It is not a day trip - if you want to fit it in, then you'd have to likely decide to not stay in Tuscany for the two weeks and move up north before heading back south. There are other places to see, but depending on your interests some will be more appealing that others. Some choices: Bologna, Verona, Padova and Ravenna are all beautiful cities which you could fit in if you want to do a week in Tuscany and another week further north. Cinque Terre is much closer and doable with Tuscany. What you end up doing depends on whether you love art and culture, history, great food and wine, hiking and walking... a mixture of all of the above! The good thing is that Tuscany and Italy for that matter gives you a chance to do a lot of all of these things.
A tentative
itinerary for Tuscany and Cinque Terre could look like this:
Even if you choose to say in the Tuscan countryside the whole two weeks, you could spend one week closer to Florence and Pisa and then move the second week and stay closer to Siena and southern Tuscany. This way you reduce travel times and concentrate day trips to the area where you currently are.
For example, some day trips in the northern part of Tuscany could be:
2-3 days into Florence
1-2 days between Pisa and Lucca
2 days Cinque Terre (so 1 night out)
Move closer to Siena and then do
1 day in Chianti
1 day San Gimignano and Volterra
2 days Siena and Monteriggioni
2 days Valdorcia
Some accommodations closer to Siena you could look into:
San Giovanni in Poggio and
Podere Cunina. These are farmhouses offering apartments without meals as a service but you could still ask, it is likely they can organize someone to come in and cook if they are given time to plan it.
Okay hope these suggestions help clear some doubts and help in the planning of your vacation! Have fun planning it all! Just another thought: having two cars might be good especially on those days when you actually want to head in separate directions if you were to have half of the group doing something one day, the other something else.
Post any additional questions you might have, I am sure we can come up with some more suggestions
