Hello,

Wanted to seek some input from the Fodor community about the end of our 20 day trip to Europe. We're spending 10 nights in Croatia/Slovenia and then 9 nights in Italy (Como, CT, Tuscany) and flying out of Florence at the end of the trip. We have 3 nights allocated to Tuscany and this will be a return visit as we stayed just outside of Florence back in 2007 hitting a full day in the city and another day in San Gimignano.

As we had seen the major sites in Florence already our main goals were 1) wine tour 2) Montepulciano 3) Siena. 4) enjoy delicious wine and cheese! Originally my plan was to just simplify and stay all 3 nights in Florence since this will be the end of a long trip. It would have looked something like this:

Day 1: Arrive from CT around 4pm in Florence, check-in hotel, stroll city
Day 2: Day trip to Montepulciano and Siena
Day 3: Small group wine tour of Chianti region, nice dinner in Florence
Day 4: fly home on 7:55am flight

Looking into things more I'm realizing that doing a day trip to both Siena and Montepulciano in a single day via public transportation would be more difficult than anticipated. So now I'm wondering if we should instead stay 2 nights in Siena before switching to Florence for final night due to flight? Or do we just drop Montepulciano off this trip do the day trip to Siena and wine tour out of Florence and keep a slower pace? Or has anyone actually done a Montepulciano/Siena day trip from Florence before?

Obviously this stuff is so much in personal preference, but I love hearing what others would do in similar situation who have already been to the places in question!

Thanks so much!

Assuming you are spending 3 nights Como, 3 nights CT, I would drop a night in CT and add it to somewhere in southern Tuscany (Siena?). If you stay in Siena for three nights, there are lots of tours that operate from there to Montalcino (although you can easily reach it by bus) and Pienza/Montepulciano (they are fairly close together).

Siena is an easy day trip from Florence by Sita bus, but not easy from Florence to other parts of southern Tuscany.

Other posters may disagree, but I'd stick with Florence and give Siena the full day. Could you have dinner in Montepulciano after your Chianti tour? I don't have a firm grasp of the geography/bus times involved. Are you taking a guided wine tour? Perhaps there is one that combines with Montepulciano's amazing wines???

If you have seen enough of Florence then I would suggest you stay somewhere else in Tuscany and plan to spend you last night in Florence for the flight home. Are you planning on getting a rental car in Italy? Two nights in CT would be my suggestion, then rent a car in CT and drive to Siena or perhaps some smaller village to use as your base for Tuscany. The area around Rada in Chianti is scenic and close to Florence so you might consider one of the towns in this area as a base.

You can barely park a car in the Cinque Terre, let alone rent one. The OP could rent a car in La Spezia. BUT s/he plans to use public transportation.

I like kybourbon's suggestion of dropping a day in the CT and basing in Siena, with one last night in Florence.

I would stay in Siena for the 3 nights and day trip to Florence. The bus will take about an hour and you will not be changing hotels again.

Wow, just went out for a jog and came back to all this great feedback so soon, very appreciated. To address some of the questions and feedback...

So this isn't the first we've been told to drop CT to 2 nights. I was tempted to but what's keeping me from doing it is I feel like 1) we'll most surely be back to Tuscany region whereas 3 nights in CT will probably give us what we need from there 2) we love hiking and picturesque towns which seems to be what CT is made for. I feel pretty good about the 3 night decision at this point for CT, but appreciate the suggestions.

As for the transportation, definitely looking to keep with public transportation if possible. We'll be renting a car for much of our Croatia trip and I'd just prefer to not do it again, plus as I told my wife a car rental doesn't go with the activity I love best in Tuscany-- wine drinking

For the wine your we were looking at two options. Either a small group (max 8 persons) guide tour or a private tour with Lucca (checking his availability). I couldn't find a small group tour that Montepulciano from Florence, although there was one to Montalcino. Is that a pretty comparable town for those that have been? Also I just realized that if we did a private tour with Lucca I suppose we could just extend it and have Montepulciano included...hmmm.

Finally as for staying in Siena all 3 nights, unfortunately that won't work as our flight home is at 7:55am from Florence. Thanks again for the continued feedback, loving bouncing ideas off other travelers!

Mirmar, our hotel in SML had ample parking for our rental car but you may be correct in terms of finding a rental car agency there. We rented our car in at the Milan airport and I'm not sure of ucfjay's arrival details from Crotia to Italy. I just think driving in Italy is very easy and with their desire to move around a car would be a good thing. But then I haven't don't have much experience with the public transportation side of things so my opinion is limited by this. My wife and I did pretty much the same trip ucfjay is asking about, that is Como to SML then to Tuscany except our trip was two weeks and we left from Rome.

Montalcino has all the Ruffino wines-that might be what you want. If you have a pile of money, you can send some home! It's a sweet town-good food too.

I found Montepulciano more interesting visually. Other posters can say. Both hill towns-gorgeous views. If it's wine, go to Montalcino.

I like both Montalcino and Montepulciano, but IMO Montalcino has the better wines (Brunellos). Montalcino always seems to have far less tourists than Montepulciano and seems quieter to me (no mini bus going through the center). If Lucca is picking you up in Siena, you could visit Montepulciano first (it's furthest), then perhaps Pienza (pecorino!) on the way to Montalcino. I'm sure Lucca can arrange a vineyard tour/tasting at some point between the towns.

The beauty of doing a tour with Luca (or at least ONE of them) is that he can tailor your day tour with him as YOU want it. He can definitely take you around easily to all the places you would like to visit and there will be no problem with driving after wine, since HE will be driving. We have used Luca for several trips and he is SUPERB and highly recommended (by many people on this board too).
Have a marvelous time.

rlbplf, Santa Margherita Ligure is not in the Cinque Terre. However, it does make a good base for visiting the CT.

We visited Tuscany between Christmas and New Year for two of the nights we were staying at San Gimignano, at a lovely Agriturismo just 900m away from the ancient city, and since you have already visited Florence, like we had, I would skip sleeping in Florence, as it is so very crowdy, always, and not relaxing at all in my opinion. We hired a car, so we were able to see so many ancient towns in just 4 nights in Tuscany. (our other two lodgings were one night on a hilltop accomodation near Pisa and the other night on Christmas Eve on a mountain village as they light up the whole village with bonfires on the eve of Christmas) So visited San Gimignano, Florence, Volterra, Siena, Casole D'Elsa - another lovely small medieval town, Pisa, and Abbadia San Salvatore (which I would not suggest as it is high up in a Mountain. There were quite a lot of tourists in Siena, but nothing like Florence, too crowdy you can barely walk on the streets,so if I were you I would find accomodation in or near Siena in an Agriturismo if you prefer quieter accomodation. We did not manage to go to Montepulciano, but we heard that it is also a lovely ancient town. If you would like my advice, I would find accomodation for two nights in Siena or somewhere nearby, and just spend the last night in Florence. From Siena you would be able to visit Volterra, which is quite near, or Montepulciano, or both if you manage to. San Gimignano is also very near to Siena, if you are considering staying there again, our accomodation was called Palagetto di Sotto. But since you have visited that town already, staying near Siena or Volterra (also high up a hill) or Casole D'Elsa would give you the advantage of saving time and seeing another town. Enjoy your stay!!!

<<I would skip sleeping in Florence, as it is so very crowdy, always, and not relaxing at all in my opinion. >>

I have been to Florence often in the off-off season and it is not crowded and quite relaxing. December through early March are the quietest IMO and IME.

Luca Garapa is an excellent guide whose company we have enjoyed on a half dozen occasions. He knows our tastes and tailors our time with him accordingly. I hope he is available for you.

Personally, I find driving in Italy stressful and avoid it.

mimar, you are correct on both respects. We found SML a good base for visiting the CT.