Comments on my itinerary from experienced travelers/

Too much time in Florence. Not enough in Rome.

Ed's probably right, but it depends a lot on what your interests are. Florence is all about Renaissance art and architecture. If that's your thing, 3 days is certainly not too much. If it isn't, then one full day is likely to be all you need. Siena is a lovely town, worth staying at least one night, though I haven't been to the other Tuscan towns to compare. It's a pretty easy day trip by bus from Florence. One of the issues that comes up regularly here is the difficulty of driving a car in many towns in Italy, notably Siena and Florence among them, because of the prohibited zones. I suggest you do a helpline search and read some of the threads before you settle on your itinerary. You may end up renting for a week in a villa in Tuscany and exploring by car all over. Or you may decide not to have a rental car at all. I'm not a big fan of Rome. For me it's a big city, without the ambience that I've found just about everywhere else in Italy. But I love the museums. Lastly, Cinque Terre are beautiful when it's sunny, and a bust when it's rainy. Doing your itinerary in reverse, leaving the CT to the end may give you a better chance at good weather - hopefully someone else will chime in about the timing. I think you are absolutely on track to decide first on your itinerary, then book your flights and then your hotels. 3 months should be plenty of lead time for hotels in April.

Thank you both. I am an artist and think I will be in seventh heaven in Florenceso I am not too worried about that. Enough time in Cinque Terre? Your suggestion to basically reverse the tripstart in Rome and do Cinque Terre last in order to capture better weatherthen flying out of Florence or Pisais definitely a good tip. I didn't realize having a car in Siena was also a big problemI did know about Florence- and that's why I was thinking of picking up the car the day we leave Florence to head south and then leave it off when we arrive in Rome (no car in Rome either). But if I can rent in Siena instead, we'll train from Florence to Siena. I understood that to explore the hill towns you really need the wheels, otherwise I might be happier without them altogether. I could investigate how much it will cost to hire a driver for just what I need (to get to and while in Montepulciano) and plan on public transportation for everything else. Any thoughts on short hires with a driver vs. the expense and hassle and freedom of having a car for that period/
Thanks again.

Susan, I've been to Tuscany many times without a car and have managed to get to lots of hill towns. It does take some planning, however, since train/bus schedules (especially before the summer season begins) might not be as flexible as you wish. Personally, I would stay the night in Siena. You can daytrip to Montepulciano from Florence in an afternoon. Another good city for art is Arezzo, east of Florence (also a daytrip). If you really want to spend more time in Florence, make Pisa a daytrip. You say you don't want to spend much time in Rome on this trip, so I won't offer suggestions there.

Thanks, Zoe. Good point on Arezzo. The Montepulciano portion is the "stand in" for the agritourismo part of the trip. The idea is that I want to stay in the countryside the hill town area and then use it as a base to see some other hill towns. I admit I am very fuzzy on this part of the trip and need to do more research; I just think I wanted to reserve the right number of days for this part. My fantasy is to do some plein aire painting while there. I just didn't know how easy it was to get around. I know that you can walk a couple of km between some villages. Depending on the family/place we stay and exactly where, they may be helpful in getting us somewhere for the day. Or we might just go wherever they are going!
Susan

Susan, As you'll be travelling in April, the suggestion from Chani to reverse your Itinerary would be good to consider. While there are never any guarantees with the weather, that should provide a better chance for sunshine. As it's your first trip to Italy, you'll have to be prepared for a bit of "culture shock", as Rome can be a bit "intense" at times. For your stay in Monterosso, I would highly recommend pre-booking accommodations WELL in advance. Do you have a Hotel in mind? Would something like this work..... > D1: Flight, BOS / FCO > D2: Arrive Rome - Leonardo Express to Termini (DON'T forget to validate!) - familiarization, jet lag recovery > D3: Colosseum, Sistine Chapel > D4: Rome, touring (Galleria Borghese, Trevi Fountain, Spanish Steps, Piazza Navona?) > D5: Train to Siena (time 3H:13M, 1 change in Florence) - take a Taxi up to the town > D6: Explore Siena > D7: Siena - Rent Car, tour area, Montepulciano (you could also take day tours - I believe there are some listed in the Guidebook) > D8: Siena - tour other hill towns > D9: Bus to Florence (afternoon), familiarization > D10: Florence - Uffizi, Accademia, etc. > D11: Train to Monterosso (time 2H:26M with 10:26 departure, 1 change at Pisa Centrale) > D12: Monterosso - hike the trails, tour other towns, trip to Porto Venere or Portofino? > D13: Monterosso > D14: Train to Milan > D15: Milan - day trip to Lago di Como (Varenna)? > D16: Flight, MXP / BOS There are many ways this could be arranged, so this is just one suggestion. The Italy 2013 Guidebook would be an excellent planning resource. Good luck with your planning!

Susan: Either your basic itinerary or Ken's itinerary would be fine. Milan's one of the better destinations into Italy, and you can get to the C/T from there easily. I would prefer spending time in other places rather than Pisa. It might be easier spend your nights in Florence and then take a bus down to Siena. (The city is very congested with apartment complexes at the bottom of the hill and parking is difficult to deal with.) Go thru AutoEurope and get a rental car as you leave Siena, and take in Volterra and San Gimignano hill towns for sure. A car is best to enjoy Tuscany.
Then driving cross country to Orvieto is easy, and it's another great hill town. Chances are you'll turn your car into Hertz across from the train station. The train into Rome is 1 hr.

Thanks,(David, Ken Zoe, et.al) especially for the suggestion about Orvieto and turning in the car there. That's great. I hadn't thought of renting a car in Siena. Of course that would be best I believe many say to plan the rental before leaving the USA, get the GPS, etc. However, I was thinking that we are then locked in to that and might find it different once we are there. Any thoughts? Some people have terrible car rental experiences, others don't find it a problem at all. Not sure what makes the difference (besides not parking or driving where it is restricted!). What is the Milan draw? Somehow, I don't feel it in what I read. But I do I was including Pisa mostly if we fly into Pisa. Otherwise, I probably would leave it off. I am not sure that Milan is one of my "have to's" this tripI just don't get the "draw" from my reading. Curious. But could be a good departure airport as you said. This feedback is ever so helpful, so I really appreciate everyone's input.
Now...just have to try and get cheaper airfare! Susan

Susan, A few additional points to add..... I suggested renting the car in Siena, as that's the area where you'll need it most. That will allow you some freedom to explore the hill towns. You could also travel from Rome to Orvieto and rent the car there, returning it in Siena. However, parking can be an issue at times in Siena, so I thought it would be good to minimize that. There is no particular "attraction" for Milan. It has some interesting sights, but doesn't have the ambience of other cities in Italy (IMHO). I suggested it as it's easily reachable from Monterosso, is a convenient "home base" location to visit Lago di Como and also (more importantly) you'll probably have to stay there the night prior to your flight home (if that's the route you choose). I wouldn't bother with Pisa at all, unless you have an overwhelming desire to see the Tower for a couple of hours. Cheers!

Thanks again, Ken. All duly noted and clarified! And appreciated, of course.

Susan, A couple of points:
The bus is easier and faster between Florence and Siena. Siena has a Hertz, Avis, and Europcar. Using a broker like Autoeurope usually gets you a better rate. Renting in Italy is usually more expensive then having it set up before hand. For hill towns see http://www.slowtrav.com/italy/tuscany/hs_planning.htm

First of all flying to Pisa from Boston is not going to be easy. Pisa has a daily flight from JFK (Delta) but it is a seasonal flight that I don't think will operate as early as April. Most other flights are EU low cost. Air France via Paris is probably the only option for Pisa in April. As suggested by others I would look into starting your itinerary from the south (Rome Fiumicino airport has more options too) and work your way north. You can do the cinque terre during your Tuscan escapade. Re: car. Negotiating Rome and Florence by car is not advisable. So your choice to rent bef or after visiting those two is wise. I wouldn't be so scared of Siena. If you visit for a day just park outside the city walls in the San Domenico (stadium) area. That area is nothing but pay parking lots. Just find one as close as possible to San Domenico church so that you don't have to walk too much to the sights. Just check google maps to see that area (zoom in on the stadium). While you have your car I would visit everything in and around Tuscany. I would leave Florence last. Return your car in Florence whaen you arrive To Florence and fly back to the US from Florence. FLR has no direct flights to BOS but you can reach it via Paris or Frankfurt or Zurich or Amsterdam (with AirFrance, Lufthansa, Swiss, Alitalia/Kim respectively). I am assuming from your post that you are not interested in visiting northern Italy. Otherwise we need a brand new discussion.

I love Milano! Apart from Leonardo's "Last Supper" (for which you need reservations), there are excellent museums, the Castello Sforzesco, and the Duomo (you can take the lift to the roof for a close-up of the gargoyles and buttresses, plus views of the city). You could spend the night you've allotted to Pisa in Milano instead and continue your itinerary.

Susan, Congrats on your upcoming adventure! I've been there twice. Once for 16 days and the other for 21 days. Take your time. Italy must be absorbed, not observed. Start in Rome. 2 days. take train only. dont get a car. you wont need it. stop in orvieto and stay the night, (or not) it wont be too busy that time of year so you dont have to have everything sooo regimented. visit siena too. ( these are in no particular order) I would do at least 2 or 3 days in Florence. Hit lucca for a day and night. make Pisa a day trip (for a half a day) Go up to cinque terra for a day and night ( take your time and enjoy the slower pace in the cinque terra.) If you find yourself with time, check out the lake cuomo area, if not go to milan and see the last supper. ( make reservation now). Fly out of Milan. keep in mind, i'm no expert but I like to go by the seat of my pants when I travel. Have fun!