Italy itinerary - some questions
 

Here is our current plan for Italy, last 2 weeks of June. There are 3 of us going, DH, me and 14yr DS. I have a few questions and would love some comments:
Day 1: Arrive in Milan 7:30 am from US West coast. Take train to La Spezia (3 hrs), bus to Portovenere. 3 nights at the Grand Hotel.
Day 2: Hike/boat Cinque Terre
Day 3: visit Santa Margharita, Portofino
Day 4: Tuscany - 4 nights. Pick up car in La Spezia, drive to Greve. Stay at a Chianti winery. Visit Siena, Florence, other places in day trips.
Day 8: Venice - 3 nights La Calcina apt. Drop off car somewhere.
Day 11: Rome train or plane to Rome. Stay 4 nights at an apt (Sleepinitaly) near Piazza Navone. Take tours of the Vatican, Colesseum

Questions:
1. Arrival in Italy: Is this too much travel at once (plane, train or even car rental)? Should we stay one night in Milan and do 2 nights Portovenere?
2. What is the best way to get to Venice from Greve? Drop off the car in Florence and take a train or drive to Venice and drop off the car? Or something else?
3. Venice to Rome: It's a 5 hr trip minimum (wish I'd noticed when I first started planning this trip!). I am thinking about flying instead (1 hr flight). The cost of the flight is $96.
Any thoughts?

i can only comment on the venice/rome piece. i would take the train- book the first class section and sleep- youre going to need it sounds like. by the time you get the airport in venice (and sounds from the fare that you will be flying from treviso) it will be an hr (actually its prob an hr to marco polo as well). you should be there 2 hrs before your flight if its a budget airline so theres 3 hrs. then in rome you'll have to pick up your bags and get to city center... thats EASILY another hr+ and I havent even counted the flight time!! I say def train it.

You don't seem to have allowed any time for jet lag. I wouldn't cut your time on the Italian Riviera. Given that you arrive so early, you might as well make your way to the coast. You must take a bus from Malpensa to Milano Centrale, before catching the train to La Spezia. And it would have been easier if you were staying in a town on the railroad. How do you plan to get from Portovenere to the CT or Santa Margherita Ligure? Bus? Boat?

We just came back from Milan and Venice & like your schedule,we arrived at Malpensa (Milan) Airport at 7:30 AM. We spent the first day and the morning and early afternoon of the second day in Milan. While Milan was mildly interesting, we now regret that we didn't head straight to Venice as the sites in Venice far surpassed the sites in Milan. Don't misunderstand, the Duomo is the 2nd or 3rd largest in the world however, the Duomo Museum is closed for renovation. The Galleria Vittorio Emanuel is interesting to walk through (a 19th century stain-glass-topped, barrel-vaulted tunnel with stores & tourist restaurants. The self-guided LaScala Opera House tour was also interesting as we are opera buffs. The Milan highlights for us were attending an opera at LaScala on the evening we arrived and visiting the Ambrosiana Library and Picture Gallery & Pinacoteca Brea Picture Gallery (both are art museums). We didn't go to Santa Maria Della Grazie (DaVinci's Last Supper) as we didn't want to take the time to wait in line. Overall, Milan is not a city I would go back to and we found the hotel rooms to be overpriced as we arrived on a week day. Weekend hotel rates are less. By the way, be sure to eat a minimum of one of your meals in Venice at the restaurant in the LaCalcina hotel in Venice. It was by far the finest and most reasonably price dinner we had the entire time we were in Venice.

I pretty much agree with what's been said already. For Venice to Rome, definitely do the train. By the time you add in your travel time to and from airports on both ends and have to arrive early at the airport, it is easier to take the train. I've done the train Venice to Florence to Rome so that broke up the train ride, which I found went by very quickly. I don't think 5 hours would seem so bad or need to sleep - enjoy the scenery and prep for Rome on the trip.

While I adore Italy, Milan is not one of my favorite cities. Yes, there are a few interesting places to see, but with your time so short, focus on the places you really want to see. When you arrive in Milan you will be jet-lagged, so definitely don't plan to drive. Although my feeling is that it's a good opportunity to make yourself stay awake by focusing on travelling to your destination. I always think it's a good idea to get on present time as quickly as possible and get your body acclimated to the new time, so travelling to the coast should help to keep you focused on a task to stay awake.

I haven't driven from Florence to Venice - only train. But I have driven from Florence into the countryside and I think that I would consider just driving to Venice...unless you have an interest in spending a couple of hours to check out Florence before heading to Venice. The city streets are very narrow in Florence and I personally found it a little stressfull navigating out of the city, but certainly doable. If you have an interest in seeing Florence, be adventurous and drive into the city. But if you don't, I think I would just drive to Venice.

From posts that I've read here, it sounds like it's easy to drop off a rental car in Venice at the train station. Then you can just hop on a vaporetto and head into Venice. You can probably search for that recommendation here, if you don't get anyone who specifically has had this experience to post to your question.

I say drive to Venice from Greve; there's just too much to explore along the way - Mantova, Montagnana (our first view of a walled city). You could make a day of it. We did the reverse from you picking up our rental car in Venice (it was a breeze) and then heading to Emilia-Romagna. We took S10 exiting south of Padova off A13. The line of cedars we saw not far from there almost brought me to tears - I was finally in my vision of everyday Italia!

Thanks to all of you for your help. I did think about renting a car and driving to Portovenere, but I am a little worried about jet lag and once I get to Portovenere, and cost - the car will just sit for 3 days with 16E per day parking fees!
Mimar - we do plan to get to CT by boat from Portovenere and hadn't thought about Santa Margharita yet, but a boat/train combo I suppose. I thought that the boat transport sounded fun. I am still 2nd guessing myself about having planned for 4 stops instead of 3 and CT/Porto. would be the one to go.
seymourbaby - I was thinking about doing exactly what you did in Milan so given your experience, I'll plan for all 3 days in Portovenere and CT. Thanks for the tip on dinner at La Calcina.
Venturegirl and tonigb:I'll take your advice and drive to Venice. That allows stopping at an interesting place for lunch and just meandering a bit, which always fun.
jtdreamz: I think the flight is from Marco Polo (Air Italia) but I was worried about all the time ahead to get there, etc. I guess we will train it to Rome. The trains only show afternoon trains, but maybe more will be added to the schedule.
All - I thought our jet lag would be taken care of by our 1st afternoon in Portovenere, hanging out, casual dinner, early to bed. I hope so anyway. I hate jet lag! I went to Bangkok last fall and had NO jet lag going over, but it took over a week, once I got home, to feel normal.