If you want to explore Tuscany in freedom, a car is usually recommended. But it is an expensive option. Another alternative would be to explore small towns via bus. So it depends on the type of experience you want.

I've enjoyed exploring small towns using Assisi as a base (which is in Umbria, not Tuscany), relying on train and busses. Perhaps you could take a similar approach with Montepulciano if you want to avoid the expense of car.

I would rent a car while in Montepulciano area. You should do this sequence:
2 (or better 3) nights in Venice
(train to Florence)
3 nights in Florence
(rent a car in Florence, head out to Montepulciano)
2 nights in Montepulciano (keep the car here and take day trips around)
(drive to La Spezia, near Cinque Terre, return your car in la Spezia and proceed by train to Cinque Terre)
2 nights in Cinque Terre
(train from Monterosso to Rome)
5 nights in Rome.

In a 14 day overall trip, I would find 5 nights in Rome excessive. I think 4 nights will do and you can add that saved night to one of the other locations depending on your preferences. For example I would add a night to Montepulciano area and use that time to visit more towns by car. Just 2 nights is only one full day after all. Also Venice should have 3 nights for sure.

The cost of a rental car is approx. $45-$50/day for an economy car (or $55-60 for a compact), full (no deductible) insurance included (the weekly rate generally applies for 5 days or more).

Since in my sample itinerary the rental days would be 4, your rental costs wouldn't be more than $200. That's a wise use of your money IMO, because small villages are more easily reached by car and you would be able to see more of the Tuscan countryside in the same time. Gasoline and toll costs are probably less than the train tickets if 2 or more people are traveling together.

Roberto has some great advice up there.

I agree with his suggestion to do Rome 4 nights. I was in Rome for 5 nights on my last trip and it was a little long. We only stayed the extra night to be there for the Lazio - Firoentina soccer game which was a nice expirence. I would drop Rome to 4 nights which still leaves you ample time to do stuff, and add an extra night to Montepulciano. And you can have an extra day to drive around Tuscany and see some small hilltowns.

While Roberto certainly gives good advice here, having recently rented a car in Italy for just a few days, I think his estimate of the total cost is somewhat low. Besides the rental fee and zero deductible insurance (which I highly recommend for peace of mind), you have gas (twice the US cost), parking fees if any, and required International Drivers Permit for each driver ($15 each at AAA, plus 2 passport photos). Then at least a good road map, although for Tuscany most people seem to recommend a GPS gizmo loaded with Italy maps.

I disagree that my estimates were low.
I tested on Autoeurope.com pick up date in Florence on Sept 2, 2014 at the Hertz on via del Sansovino and return on Friday Sept 5 at La Spezia.
A Fiat Punto (Economy Car) with no excess insurance (zero deductible) was quoted for $145 for the 4 days (~$36/day). A Fiat Panda (economy) with Europcar, same insurance terms, days and cities, was quoted for $190.
Kemwel.com gives me even more favorable terms. An Economy car with Europcar for $101 for 4 days with no insurance excess (zero deductible), same days and locations.
Gasoline (or more often diesel fuel) is expensive, about €1.75/liter ($9.50/gallon), but those cars easily get 18-20km/liter (~45-50 mpg) and distances aren't long in Tuscany. From Montepulciano to La spezia it's about 250km and on average, doing day trips in the area you won't travel more than 150-200km/day. So even assuming you rack up 600-800km driving around during those 4 days (which would be a whole lot IMO) , at most you will use 30-40 liters of fuel (about 50-70 euro) for the 4 days. Most roads and even freeways you will be on have no tolls, therefore freeway toll costs will be insignificant.
So Rental costs + fuels and tolls won't be more than $250. At the same time you will save on train and bus fare (times the number of people in your party), but above all you will save on time and flexibility, because the small towns of Tuscany do not have frequent bus service, especially on Sundays when bus service is minimal.

The only way to know how much time you need in a city is to decide what you want to see there. To me, 5 nights in Rome is not nearly enough but it depends on what you want to see and do. You may find you need more time in Florence and less in Rome or the reverse. Before making hard decisions on how long you'll stay in a location make a list of what you want to do and figure out the timing from there.

Donna

I also favor Roberto's advice of three nights in Venice and three nights in Tuscany and Umbria. While I've come to like Rome better, I really preferred Siena, Orvieto, and the other stops on my first visit.

Wow! I am so hapy for all of the replies. Thank u..

After reading each response it seems that renting a car is not that much more expensive. (There will be only the two of us). If we take a night from Rome and use it for Tuscany villages (3 Total nights),could we see Montepulciano, Pienza, San Gimignano, And Siena in that time? And all before heading out to Cinque Terre area? Also, would it still be best to stay all 3 nights in Montepulciano? Or switch to 2 nights Montepulciano, and 1 night elsewhere on our way to CT?

Looks like this:
3 nights Venice, train to Florence 3 nights, rent a car and drive to Montepulciano-rural tuscany for 3 nights visiting the area by car. Drive to La Spezia and drop car off. Train to Monterosso stay 2 nights. Train to Rome and stay 4 nights.

bliss,

I also agree with Roberto's advice. Using a rental car is a time-effective way for getting around hill towns that aren't well served by frequent public transit. However, a few points to mention.....

• As someone else mentioned, be sure that each driver has the compulsory International Driver's Permit, which is used in conjunction with your home D.L. (so you'll have to bring those as well). I.D.P.'s are easy and inexpensive to obtain at any AAA office.
• Be SURE to do some research on the dreaded Zona Traffico Limitato (limited traffic areas) that are common in many towns and cities in Italy (especially Florence). Some of these areas are "limited" during certain hours on work days or whatever. You may find it helpful to have a look at THIS website or THIS website on the topic. Violating these areas comes with hefty fines, which you likely won't know about until several months after you return home. The first clue that fines are coming may be a charge on your credit card from the rental agency, for providing renter information to the authorities. The next thing will be a notice from European Municipality Outsourcing with the ticket details. By the time you receive the notice, it will usually be too late to dispute it (a difficult process anyway).
• Having a GPS is useful for getting around the rural areas of Tuscany, but if you don't have one I'd suggest packing along a good Map.
• I'm not sure what the current situation is with toll booths in Italy accepting non-Chip credit cards? It might be an idea to keep some small change at hand. Hopefully Roberto or one of the others can clarify that point.

Happy travels!

I just did an itinerary for first-timer friends. Being in your 20's the trip should be a breeze with a Euro railpass (travel first class and save money by not renting a car). I'm from LA too, but I would definitely skip the driving on your first trip. Italy is our favorite country in the world but it is a "different world" compared to the rest of Europe!! Rick saves you tons of time and tons of dollars and tons and tons of hassles. Get Rick's "Pocket" books on Venice , Florence and Rome - these act as your tour guide inside the major sights meaning you can follow Rick's "masterpiece" map through the Vatican Museum in two hours instead of two weeks (we're talking 4 miles of art here!). He also has one on CT as well that we have used. His stuff is great, I can not emphasize this enough. Ninety percent (no exaggeration) of the tourists you'll see will stand in LONG lines and once inside will not have a clue as to the significance of what they're looking at, RS brings all this to life in synopses in the book you carry. Note: use your iPhone for pix and forget about trying to read it or an iPad with downloaded books. They get cumbersome, are hard to read because of glare and are thief magnets who run by you swiping it from your hands.
Can you tell we've experienced all of these things! I'm not trying to tell you what to do, of course, but I know how different Italy is than the rest of Europe - it's fascinating but can be incredibly frustrating on your first trip when the hassles start building up when you always seem to be lost, behind schedule, and the money is burning up fast. Some more important tips: carry all your luggage on/use the kind that has backpack straps (one suitcase, one small bag only - no one cares what your wearing); wear a money belt; follow RS's guidelines for these items. More tips: use Airbnb for lodging, Rick or the locals for food and keep a small daily journal to jog your memory later - stuff starts running together fast! Buy the Roma card and Firenze card and make a Resv. at the Borghese (don't miss this) in Rome before leaving the US.
OK, suggested itinerary: Venice 2 nites, Florence 4, Assisi 1, Rome 4, Siena 1, CT 2
You can add a nite in Venice if you arrive late; Flor to Assisi is on everyone's list of "scenic train" trips;
It's cheap to fly in and out of Geneva or Zurich (pricey lodging tho). If you "redeye" in you can be on a train in less than 30 minutes traveling some of the most scenic trips on Earth (Switzerland and Austrian Alps) on your way to Venice and leaving from CT. Use Ricksteves.com, plan as early as possible and print your tix at home for major sights. Misc: Rome-don't lodge to the west or south of train station; in Flor it's a no on the NW side. Taking a siesta, especially on long hot days, charges the batteries fast for strolling at nite and eating at 9pm. The nights in Venice, Florence and Rome (actually almost everywhere in Italy) are very unique, special and dare I say, magical. Yeah, I do say so. Ciao Bella!

I want to thank all of you again, and ken and Jim-Bird as well for recommendations-- I will look into RS's books.

After thinking long and hard about the car idea, and seeing many places.. We decided it may be too crazy for a first trip.
By cutting down on getting the car and possibly limiting the amount of hotels, our trip may feel less rushed. Regardless, we will Fly into Venice and out of Rome.

Remade Itinerary to the following two options
Does this look right?

1

3 nights in Venice
train
4 nights in Florence (day trip to Siena)
train
3 nights in Cinque Terre
train
4 or 5 nights in Rome

2

3 nights Venice
train
3 nights Florence (get roundtrip train tickets to CT area)
train to CT
2 nights Cinque Terre
train to Florence, Bus to Siena
2 Siena
Bus to Rome (same time as train but cheaper!)
4 or 5 nights Rome

If you add that 3rd night to Tuscany and take it away from Rome, I would look to stay in a different city. Montepluciano is the south part of Tuscany. You mentioned San Gim in one of your replies, you can spend a night in a northern Tuscany town instead of back tracking to Montepulicano and back to La Spezia again. Maybe on that day you can visti San Gim in the monring/afternoon and maybe a place like Volterra for 1 night. It's close to San Gim and you can explore volterra in the late afternoon. Then be on your way to La Spezia the next day. 2 Night Montepulciano, 1 night Volterra (or something up there)

Bliss,
That looks great and your comment about not being too rushed is so true. A few more tips and again, these are only suggestions you may want to use. Rome - Rick's Campo di Fiori walk is really cool (we did it for a breakfast start at the fabulous open air market) - this was a "leisurely" day after a couple major-sight days. Skip Rick's other walk, it's a little too Gucci/big downtown LA/construction zone stuff. There's something very special about the Pantheon that I can't put my finger on. I could stay there for a week. It's the oldest continuously occupied (since the first century) building in history. Raphael and the first two kings of Italy's tombs are there. Read RS backstory on the Pantheon, Bruneleschi and the Florence Duomo dome.
Siena between 10am and 3pm is a zoo with tour buses but is divine at night. St. Catherine's head is not for the skirmish but read Rick's write up.
Depending on how much hiking you want to do inCinque Terre, your railpasses should allow you to take several 10-minute rides up and down the coast and you might want to do Portofino/Santa Margharita too. We took a fabulous boat ride from Monterosso to Riomaggiore hitting Vernazza and Corniglia along the way. Try a mojito at Bar Centrale in Riomaggiore - they're about €6 but worth the splurge maybe even w/o an ocean view.
Have a wonderful time!