first trip! would love feedback from the experts...

My husband and I just did a very similar itinerary:
Venice 3 nights train to
Florence 3 nights
Rental car 6 nights- 2 in Siena, 2 in Montepulciano, 2 in Assisi, dropped car Spoleto then train to
Rome- 5 nights.

If I could do it over I would have stayed in Florence for 4 nights and done Siena as a day trip. It was so difficult getting into Siena- you will not need or want a car there at all- we intended to take a day drive on our 2nd day there but it had been such a hassle getting parked and into our hotel we opted to just stay put. While we liked Siena- the Duomo is fabulous- we didn't like it as much as we thought we would and regretted 2 nights there. For a “pedestrian only” center it is incredibly busy with car traffic!

That said- since the Chianti and Tuscany areas you want to see are all so close- all can easily be reached as day trips and you can combine several hill towns in one day- an hour to here, 45 min to there, etc- I would suggest basing yourselves for 3 nights somewhere central- perhaps an agriturismo or an easier to access hill town. We loved Montepulciano and Pienza.

Those one night stays take a lot of time/effort- I would aim for at least 2 night stays when possible, 3 is even better. I would suggest this:

Venice 3 nights
Florence 4 nights with day trip to Siena
Pick up rental car
Tuscany Hill Town- 3 nights
Orvieto- drop car then stay 1 night
Train to Rome 4 nights

Or you could go from Florence to Siena via bus or train, stay 1 night then pick up your rental car in Siena.
The drive from Florence to Siena along Chianti Road was fine but so short- not sure that area really needs a full night.

We stayed at the beautiful Palazzo Carletti in Montepulciano, has dedicated parking spots just outside the wall- a very short walk from there to the hotel. Super easy to come and go. We hated to leave and wished we had stayed there all 4 Tuscany nights!

Other hotels- I did post reviews for some of these:
Venice- Hotel Ala
Florence- Hotel Calzaiuoli
Siena- Palazzo Ravizza- see my posted review
Montepulciano- Palazzo Carletti
Rome- Albergo Cesari

All were great for location, bkft, comfort, etc. I would stay at any again except the Palazzo Ravizza in Siena.

Christine's first itinerary is perfect. Agree that I'd spend the nights in Florence and just day-trip to Siena. There's no reason for an overnight trip/parking/hassle, since it really can be seen in a day. Florence needs three full days if you enjoy art at all, and the Piazzas the Piazzas (sigh).

I found Siena to be a great base for visiting southern Tuscany. A few years ago I stayed at Hotel Minerva, which has onsite garage parking (small fee). It's near one of the town gates and away from the ZTLs. Walking or taking the local bus into town was easy. I would spend three nights in Siena and daytrip to Arezzo, Montalcino, and other towns. I was with friends and we visited two towns each day (by car) and enjoyed our "routine" of evenings in Siena.

All good tips. If I could do it over again I'd visit Siena, or Siena and San Gimignano by bus as a day trip from Florence.

I wouldn't rent a car to depart Florence but use the train to get to your next base and pick up rental car there. Unless you have a winery tour/tasting plan for driving S222 south, you can save time & money by not renting a car in Florence.

Pick one place in Tuscany or Umbria and use it as a base for your day trips. Orvieto is actually our base choice for our next trip.
Any town/village that pulls your heart will be a good home base.

Enjoy!

Our original plan had us taking bus to Siena and picking up rental car when we left there but we really needed an automatic- neither have driven manual in over 25 years- and those were only available at Florence locations. We had no trouble at all getting out of Florence- picked up at Hertz Sansovino location.

Just something to keep in mind.

I still think Florence is worth four nights. Siena a day trip. In fact, I've returned to Florence several times, and have skipped Siena. It's main piazza is pretty sure, and we know what color it is. But the art and charm are in Florence. The Arno River, Ponte Vecchio, Medici Palace, Ufizzi, Accademia, Santa Croce Church, Piazza Michelangelo, Mercado Centrale, Piazza dela Signoria (sp) .........then rent the car on the way out and stay in an agriturismo for seeing the rest of Tuscany. Christine's first suggested itinerary.

I still think Florence is worth four nights.<<

I agree. We happened to be there on a Sun and Mon and it was difficult to plan with all the closings. But we still managed to get to all of the major sights Donna has listed...plus a few more. It was a very busy Tuesday for us!

I can't say that I disliked Siena, I was so sure I would really love it and went for the 2 nights but it was not at all as charming as Florence. Can't really put my finger on why we did not love it- I think it was just so busy, so surprised at the amount of vehicle traffic in the center, did not have a warm welcome at our chosen hotel... not sure.
The Duomo was amazing and I would not have missed that for the world, Il Campo was kind of blah to us- nice to look at but just did not have that "charm" that the piazzas in Florence did, nor the amount of really wonderful museums, churches, views, markets, etc.

CristineH, I went to Florence with my best friend and rented an apartment in Florence for a week. We both had college students studying there. We day-tripped to Siena, with hopes and dreams of a magical place. We both said, "I don't get it." She's a sculptor/artist. The next trip we took our husbands, same apartment for an entire week to Florence. We loved it so much, and I only threw the 'high points' out there for the OP. We were very busy. But I hate to see when people day trip to Florence and spend days in Siena, but everyone has their own tastes/loves.........and maybe it just wasn't our cup of tea so to speak!

I am glad that we experienced Siena at night. There was a magical feel about it and we did have a fantastic view from our terrace. But one night would have been fine.

thank you to my new travel friends. so helpful. i love the vibe on this forum...no attitude just helpful advice. here is our revised itinerary:

fly into venice- 3 nights
train to florence-4 nights
rent car drive to montepulciano-3 nights (stay in agriturismo)
drive to orvieto, return car-1 night
train to rome-4 nights

better?? we will add in some day trips from florence and perhaps venice as we continue to fine tune.

if you loved a hotel, tour, day trip, restaurant in any of these places, please share. or any travel italy tip at all. and again..grazie! (would especially love and appreciate hotels ideas! that's next in our plans)

Who is in your travel party?

We thoroughly enjoyed the Secret Itineraries tour at Doges and the Cicchetti Tour with Alessandro in Venice.

http://palazzoducale.visitmuve.it/en/pianifica-la-tua-visita/secretitineraries/
http://www.schezzini.it

In Venice I loved the sweet little Bel Sito & Berlino. My niece stayed in Hotel Ala, and she loved that one as well. Bel Sito had a really nice breakfast buffet and was located very close to St. Mark's Square. It was situated on a canal, and we got a private water taxi ($$$) for an early departure to the States. In Rome, because I Always go to St. Peter's/Vatican, I love the Hotel Alimandi -- either the Alimandi Vaticano or the Alimandi Tunisi. I enjoy the quiet of the neighborhood at night, and the fact that the neighborhood behind these hotels is mostly Residential, and the restaurants, especially Piacere Molise, are authentic and less expensive than in the higher touristed areas.

No hotel recs for Florence, as I've always rented the same two bedroom apartment, VRBO#68776. It's in the Santa Croce neighborhood, and I like that neighborhood as well because of the quiet/residential vibe and yet it's close enough to walk to
the major sites.

Funny how everyone has their own opinions of what they like. We loved Siena, one of our favorite places in Italy. In fact, we couldn't wait to get out of Florence with the Vespa's screaming around, breathing exhaust from all the cars and vespa's, noise, etc. When we got to Siena it was quiet, pedestrian streets, wandering the small streets up and down the hills etc. We were there for three nights and loved every bit. We rented a car and drove to hill top towns from there. We did stay in a great B & B in Siena with a beautiful terrace with gorgeous views. Maybe that made the difference for us? We love Siena!!

Your last itinerary you revised at 8:40 of 11/2/2014 has my official Florentine Seal of Approval.

Although I would choose as a base an Agriturismo somewhere near Colle Val D'Elsa or Siena instead of Montepulciano. Nothing against Montepulciano, but Montepulciano is a drive through curvy roads from the freeway. So for day trips it's better to be along the Florence-Siena freeway half way between the two cities (more or less near Colle VE.. That would make it easier to drive to Siena, Volterra, San Gimignano, Certaldo, Monteriggioni, Castellina (Chianti), Montalcino, Pienza and even Montepulciano.

In Venice, we enjoyed All Amarone wine bar/restaurant - portion size was just right for us (good Caesar salad), lots of wine if you like that kind of thing (we don't) - even the soda prices were reasonable - but they are a little hard to find. We stumbled onto them down an alley (we were staying very nearby Sant Aponal - it's less then a 10 min walk from Rialto). This was our 4th stay in Venice, and I must say, this was our fav restaurant (I only wish we had found them 3 trips ago, and before our last night on this stay! Oh well, I'm going to remember them for next time)

http://www.allamarone.com/

Also, after sampling lots of gelato, my fav (the black cherry) in Rome was Don Pepe. It's on via San Giovanni in Laterno, 40. Very near the Colosseum. We actually had an airbnb on via Ostilla (with a view of the Col from the window) and this was right downstairs. Again - I wish I had went in on the first night of our stay instead of the 3rd. The coconut and dark choc was also divine, but the black cherry was hands down my fav.

http://www.eyesofrome.com/recommendations/the-best-gelato-in-rome