Thanks Lynn, yes I have to get that map! I'm obviously very early in my research but I'm working on it. Much appreciate your help.

Yes, where you are flying in and out of and how you will be travelling - hire car or public transport - are key. Also agree with Lynn that you have much to much on your wish list. Just a couple of initial thoughts - the journey from Tuscany to the Amalfi is a long one, I'd be tempted to stick to Tuscany for this trip. May is a great time to be in Italy, usually nice warm sunny weather, very green, spring flowers etc. Barga is a nice little town, but if you are based in Montepulciano for 5 days, you will have already seen some of Tuscany's finest hilltowns, so I am not sure it is worth going all the way up there when you have so many places on your wish list. It would be a shame if your friends at least didn't have a day in Florence.

Thanks Peggy, yes I agree with your comment about Florence. I think they should see it. I also agree that Amalfi is just too far away and will have to be another time, maybe. My hubby and I have been there anyway but thought it was so lovely our friends would enjoy it too. Appreciate your thoughts on Barga, perhaps we'll give it a miss as you suggest and May sounds like the right time. Thanks heaps! Any good suggestions on accommodation in the places we are thinking about? ;)

Flossy,

This will give you some ideas slowtrav.com/italy/tuscany/hs_planning.htm

Thanks so much travelsitaly! I'll read this one for sure - all ideas are greatly appreciated :)

Hello lovely people! We have had a meeting with our travelling buddies and the situation has changed a bit. One of them would like to visit Venice, Florence and San Marino so we have added a more days to the trip in Italy to do these places.

We have decided to give Positano a miss as it is just too far south.

Where we fly into Italy we don't really care but at some point I would like to spend a couple of days in Milan so it sort of makes sense to me to start there. Maybe you have better ideas...

We have now these places on our list travelling in this order but if it is all crazy and we should do it another way then I'd love you to say:

Milan - 2 nights - train to Cinque Terre from Milan is that possible?

Cinque Terre - 3 nights - collect car from here (is that possible and if not where do you suggest?) and drive to Lucca

Lucca - 1 night visit Pisa on the way to Florence

Florence - 2 nights (leave car here) and train/bus?? to Siena or do you think we should keep the car?

Siena - 4 nights - day trips to Castellina/San Gimignano; Montepulciano; Montalcino - other suggestions about this please?

San Marino - 2 nights - should we continue to drive from Siena to San Marino or is there a better way to get there?

Venice - 2 nights - how do you suggest we get to Venice from San Marino?

Fly out from Venice. Is that possible???

Now, I like the idea of having a few bases and I think we can do that in Siena but before and after Siena I am really stumbling. Also, do you think the way in which we arrive in Siena from Milan is the best way to go? I'm not sure the best way to get to the places, whether to keep the car, drop it off, catch buses, trains or whatever. I have tried to use Google maps to plan it and have read quite a bit in the Slow Travel website as well as Tripadvisor but I still feel as though I'm in a mess. Please, any help you can give is greatly appreciated. I am so confused! :( Hugs to all that have helped so far and to any that can lend a hand from here on as well :)

And I just had another thought, perhaps we could go from Lucca, to Pisa and then on to Siena and once leaving there catch the train to Florence and a train from Florence to Venice but I don't know where that leaves San Marino. Perhaps we just can't go there :( My friend would be disappointed.

There are direct trains from Milan to La Spezia - details on Trenitalia website.

Continue by train to Pisa-Lucca-Florence. They are all on the same line (luggage can be deposited at Pisa Central station while you visit) - details on Trenitalia website

Collect a rental car when you leave Florence and drive to Siena. From there drive to San Marino and then to Venice where you could return the car.

I still think you are making too many stops with only time for cursory visits. A detailed hard-copy map IMO is essential reading for you and your friends as in some of your suggestions you are back-tracking

Good to see Florence in your itinerary...it is my favourite city in Europe. And I always base myself there for daytrips (even though like you I've been there before and extensively!) because I love the city at night. While there (whether as a base or for a couple nights only) make sure you have a pizza at Ciro and Sons...my favourite pizza of ANYWHERE (if you like thin style). You could consider staying at the Hotel Burchianti which is only a couple doors down...which is the hotel I always stay. Hopefully Mario and his son are still managing the place :-) Classics at breakfast time. Course if you have a higher budget, get something more posh.

Also, one of the most underrated daytrips from Florence is right on your doorstep there if you decide to stay longer, in fact can be called a half-day trip...get a local bus straght up to Fiesole (not sure how long it takes, but to put it in perspecive, I actually WALKED both up and down). Nice tiny town with lovely wooded walks (going through even smaller "towns") and a spectacular view over Florence (if you are lucky enough not to get a hazy day).

Make sure San Gimignano is one of your daytrips...its my favourite. Everyone saids its over-touristy...well, I don't mind a few tourists. Quiet towns are not really my thing. Also make sure you tour around it on the outside of the walls if you have a nice day...great countryside views. And a little hidden tip, find the little museum with multiple stories...while on the stairs there is a window that gives you the best in-town view of SG...ask the nice lady at the bottom if you can take a photo from that window (you are not supposed to take your camera upstairs). She will let you and you will get a fantastic shot of San Gimignano with several of the towers.

Milan to Cinque Terre is easy by train...in fact thats what I did, and I even had to come from Varenna (Lake Como) first. Personally I'd skip Milan altogether, but thats just a personal choice. And I guess you have to fly in somewhere. I did Milan as a daytrip from Lake Como...didn't even bother to stay the whole day. In CT, I'd try and stay in Vernazza or Riomaggiore...if the latter, try and eat at La Lanterna, a tiny little restaurant near the water.