I am going to rent a car in Florence for four days and drive south towards Montepulciano and then drive to La Spezia to catch a train to Cinque Terra. I would like to spend the night in Siena. I cant decide if I should spend one night in Siena going down and two nights in Montepulciano or two nights in Montepulciano and one night in Siena on my way to La Spezia. My husband and I enjoy driving and stopping along the way. Any suggestions would be appreciated.

Montepulciano is tiny but Siena is large - more diverse for two days than tiny Montepulciano though I guess if you just want a place to sleep OK but to spend a whole day in Multepulciano itself would be a bit much - but not Siena - Siena is also much more lively at night if that makes a difference - lots of folks doing the typical Italian Passiagetta (sp?) or nightly stroll between gelato stands and caffes.

a particularly scenic, short and pleasant drive is from Montepulciano/Penza, to the abbey at Sant Antimo. A stop in nearby wine town(brunella!) of Montalcino is also a good stop for you. Going northwest, I like Volterra near San Gimignano, for its Etruscan history and ruins.

Take the Chianti road from Florence (222) if you want a scenic drive. You can continue to either Siena or Montepulciano. I don't think two nights in Montepulciano is too much as I assume you will drive around to nearby hill towns also. Really two nights in a location is only one sightseeing day. Siena is much bigger. Parking will be an issue for both.

If you end with Siena, you can take a route through San G/Volterra area on your way to La Spezia.

You have posed the question as a routing question. If you already know the issues with driving around Florence, Siena, and Montepulciano, you are getting the relevant recommendations. If you don't know if "enjoy driving and stopping along the way" is the same thing in this area, you would probably need to clarify that part first. There are PIAs with driving with each of the three cities you mentioned. Parking, mentioned by kybourbon, is just one of them.

Montepulciano is not tiny--it is a thriving small city of about 12,000 people.Yes, smaller than Siena but much larger then the other hill towns of the region.

"...I guess if you just want a place to sleep OK but to spend a whole day in Multepulciano itself would be a bit much..."

Well...I am spending a week in Montepulciano and I'm very MUCH looking forward to it.

We've spent a week in Montepulciano and would do it again in a heartbeat. The town may not be the smallest in the area, but the main street in its historical center is only a mile long.

Several years ago, we thought Siena was a delightful base for exploring Tuscany. When we re-visited for a week in October, we were dismayed at the rush hour traffic we had to drive through twice a day. Would I stay there again? Probably not.

If I had limited time between Florence and La Spezia, I'd stay in northern Tuscany: Chianti villages and towns, Siena, Monteriggioni, San Gim, Certaldo, Volterra, Lucca, etc. You won't run out of sightseeing.

>>>Well...I am spending a week in Montepulciano and I'm very MUCH looking forward to it.<<<

A week in each town would be great.

What wonderful responses. I believe we will drive from Florence down to Montepulciano (sr222) and stay two nights then travel to Siena for one night and on to La Spezia (via Volterra) to return our rental car and take the train to Cinque Terra for three nights.

Our itinerary is as follows
Vencie - two nights - take train to Florence
Florence - Two nights - Rent a car
Montepulciano - Two nights
Siena - One night
Cinque Terra - Three nights - return car in La Spezia and train to Rome
Rome - Two nights

I realize that many people would not enjoy this fast paced trip but we are looking forward to visiting many areas and then in the future we can settle down on another trip.

I suggest Palazzo Ravizza in Siena. It's inside the city walls, not too confusing to find and has its own parking lot. You're allowed to drive to the front door to check in and drop luggage before circling around to the back to park. The walk to the Campo isn't very far. Ask for a room on the garden side although the afternoon sun can make rooms warm. FWIW, we weren't impressed with their restaurant recos.

http://www.palazzoravizza.it/

I forgot to add my Montepulciano suggestion... It's tiny, so book early.

http://www.locandasanfrancesco.it/index.php

Jean, the place in Montepulciano looks really nice.

omar, your itinerary is way too busy for me, but I do understand the concept of a recon trip. Have a great time.

Your trip sounds perfect. We did something similar our first trip to Italy. In 2011 we went back for a week in Rome, two weeks in Umbria, and another 8 or 9 days visiting Cinque Terra, Parma and Cremona, and ending with 5 nights in Bellagio. Having more time is a luxury, and knowing what to do with it is helped by having done a sampler like you are planning.

I would take a night off CT and add it to Siena.

It's all too many 2 nighters for me - too many hotel changes in such a short time.

Yes, we will be very busy but wanted to explore and check out before we decide where to go on our next trip. We are foodies, although expensice, facncy is not necessary, just great local food and atmosphere. Any restaurant suggestions for Montepulciano or Cinque Terre?