Rental Car/Trains in Italy

You have a good plan. The train from La Spezia to Siena is slow and requires 3 trains, so rent your car in La Spezia. (We did trains form Vernazza to Siena once and it took almost 4 hours adn 4 trains!) Do you have a place to park in Siena? Very important! I would drop your car in Siena when you are finished and take the train to Firenze. You can drop your car near the station in Siena as I recall.

To Monterosso from Milan is easily reserched at www.Trenitalia.com.

Have you already been to Florence? If not, I would train to Florence and spend some time before moving on to Siena. Even if just for the day to see the David (not on Mondays and make a reservation). From there bus to Siena. I'll be heading to Siena next month and plan to rent a car after my second day there. I will want to explore Siena and won't need to deal with the expense or parking until I am ready to move on to smaller towns.

Your plan is good.
Train Milan to Monterosso:
Do a search on www.Trenitalia.com to see the schedule. Use a date in the next seven days as a test.
If you depart from the city of Milan, the train station you need is Milano Centrale. If you go straight from the airport, you need to take the Malpensa Express train from MALPENSA AEROPORTO to MILANO C.LE then MILANO C.LE to MONTEROSSO. Some trains require no change. Others require a change in Genoa or Sestri.

Rent a car:
Use a consolidator: www.kemwel.com or www.autoeurope.com (same company but different prices, so check both). They work with the major rental companies ( Europcar, Hertz, Avis, etc.).
Your pick up city is La Spezia, your drop off city is Florence. Drive from La Spezia to your Relais in Siena. It's located outside of Siena in the countryside, so you definitely need a car.

I don't know where your hotel is in Florence. To avoid getting lost in the city of Florence and incurring into fines return your car at any of the following locations, depending on which company you end up using:
EUROPCAR: via Forlanini, or Airport (A1 freeway exit: Firenze NORD)
HERTZ: via del Sansovino (A1 freeway exit: FIRENZE SCANDICCI)
AVIS/BUDGET: Airport (A1 freeway exit: Firenze NORD)
Once you drop off the car, ask the agent to call a taxi, and take a taxi to the hotel. If your hotel is within the ZTL you could go inside to drop off your luggage first, but it gets complicated, and some hotels are simply unreachable by car. Just take a taxi from the rental office.

thank you everyone for your advice!

I think I have decided to drop off the car in siena before i go to florence for four days.

any good day trip recommendations out of florence? i'm there for four days at the end of my trip - and was thinking about doing a day trip the last day.

also, in terms of renting a car in september for pickup in La Spezia, and dropoff in Siena, do I need to book it now? Or can I wait until mid to late summer and wait for a good coupon/deal to come up?

Or, if i wait until mid summer, will availability of rental cars become tight for that time of year in la spezia?

If you book your car now through Priceline you can go for the cheapest price and have the guarantee of having a car. You do not prepay, you simply reserve the best price at any of the offered companies. Then, check back regularly and if you find a cheaper rate simply cancel the current reservation and make a new one. I do this all the time and frequently save hundreds of dollars over the first price I saw. I would never prepay a car reservation... they can change at any moment, and I want the cheapest rate.

kathryn,

a good idea, but when booking via priceline, it is unable to even bring up results for la spezia pickup a d dropoff in siena. it says no results available. so obviously, for some reason that makes sense to me, they dont book for pickup/dropoff in those two towns in conjunction with one another.

i'm going to repeat this question from an earlier post - apologies - just no responses yet:

any good day trip recommendations out of florence? i'm there for four days at the end of my trip - and was thinking about doing a day trip the last day.

Siena, Lucca, Arezzo, Volterra, San Gimignano - all good for day trips.

we're already going to be in tuscany for three days before florence - i was thinking of a good day trip destination out of florence elsewhere. train or air travel is fine. just looking for any good recommendations that are doable in a day.