Help with itinerary for 9 days in Italy

For me, this looks very aggressive. Is the Swiss portion of your trip equally busy? You're really short changing each of these cities, allowing only enough time for the most superficial "check the box on my travel list". I think you'd enjoy Rome and Florence much more if you scrapped Venice for this trip, and added those days to them.

Day17: Back to Milan by evening, flight back at 8pm

You will need to be at the airport by 5pm. Check the Trenitalia website for train times and leave yourself a good cushion of time. It's almost 3 1/2 hours from the Venice S. Lucia station, or almost 3 hours from Florence; assuming you take the Freccia train to Milan, then change to the regionale to the airport.

Assuming that you will have accommodations reserved in advance for your stays in each city, I don't see any reason not to buy your train tickets in advance, to get the super saver prices. You will already know which days are travel days. And there is not a separate reservation fee when you buy tickets on the Freccias. That's only if you are using a rail pass, which is rarely worth money on an itinerary like yours. (A Swiss rail pass may be worthwhile - can't say for sure, since I don't know what you're doing there. )

I'm not aware of any rail passes that give you free or discounted entry into attractions in Italy.

I agree with absolutely everything CJean said, including the suggestion to drop Venice (and I'm a huge fan of the city).

Agree with dropping Venice. You aren't giving it enough time to be worth all the travel time. I would add a day to Rome. That would give you 4 nights Rome, 4 nights Florence.

I also would consider going to Lucca along with Pisa, since you want a day trip. Pisa can be seen in a couple of hours, Lucca is much more enjoyable. Or you could day trip to Siena, a fairly short bus ride.

Thanks a lot for the suggestions. Even I felt the plan was ambitious, but it seemed wrong to leave venice out.

Will probably fit in a day trip to Siena if I leave Venice out. I guess adding a day in cinque terre will again be pushing it.

Just in case my wife insists on covering Venice, should we add a day extra there at the expense of Rome or Florence?

I guess adding a day in cinque terre will again be pushing it.

Just in case my wife insists on covering Venice, should we add a day extra there at the expense of Rome or Florence?

Yes, adding the Cinque Terre would, even more, be "pushing it" than your plan for Venice is.

If your wife insists on Venice, drop Florence or Rome. You really need to stick with two locations for this amount of time. Florence and Venice OR Florence and Rome OR Rome and Venice OR Rome and Florence. WIth 10 nights you could do all 3, just.

Suppose I buy a rail pass
1. How much would the reservation fee cost for the fast train between rome-milan or florence
2. Does the reservation fee also go up just like the full ticket price

I was wondering if this can be used as a hedge against any price rise. Basically buy the pass and then reserve the seat at a later date. That way I won't be affected by the higher ticket prices while still maintaining some flexibility with respect to date or time.

If your wife insists on Venice, drop Florence or Rome. You really need
to stick with two locations for this amount of time. Florence and
Venice OR Florence and Rome OR Rome and Venice OR Rome and Florence.
WIth 10 nights you could do all 3, just.

Totally voting with Laurel here: drop one of your locations. You don't have time to do justice to all three with just 7 days (I'm not counting arrival and departure days), and location moves eating up 1/2 days of two of those. It could also be stressful for your 8-year-old.

You might have been able to do it if you flew directly into Rome and out of Venice or vice versa but a previous post indicates that you're killing all of day 9 on a train from Luzern>Rome via Milan, and a big chunk of day 17 in transit to Malpensa (this is the airport you're flying out of?) from Venice. Malpensa is a minimum of 3.5 hours from Venice and will involve a train change.

I was wondering if this can be used as a hedge against any price rise. Basically buy the pass and then reserve the seat at a later date. That way I won't be affected by the higher ticket prices while still maintaining some flexibility with respect to date or time.

Rail passes are not a good bargain in Italy. Try to buy your tickets at least a couple of days in advance and you will (likely) get a small discount.

Train fares for the fast trains follow dynamic pricing like airfares, so it makes sense to book early. Only problem is that the trenitalia site may not accept foreign credit cards. Any workarounds? Alternate websites?

Trenitalias fare structure is not what I would call dynamic pricing. Rather, there are varyng classes of tickets (base, economy, and supereconomy), with the cheapest being limited to a certain number per train. Once they're gone, other seats may still be available, but they will be at the higher prices. But the prices have already been set.

I've booked lots if tickets on the Trenitalia site with my Canadian CC. Never had a problem. No idea what country yours is from, but you may need to enable Verified by Visa, or the MasterCard equivalent. Or try trainline.eu to book, instead if Trenitalia.

Some folks have had good luck using PayPal on one or more European rail websites. I'm not sure Trenitalia has been reported to be problematic. Renfe (Spain) is a known problem.

Sometimes you need to notify your credit card issuer that you're about to start making purchases on European websites.

Combine your Rome-Florence travel day with your Pisa excursion, giving you an extra day for Florence (or Rome).

Day09: reach Rome (3N) by evening
Day10: Rome local sights
Day11: Vatican
Day12/am: train from Rome to Florence, store bags at SMN station
Day12/pm: local train to Pisa, then return to Florence (3N)
Day13: local sights Florence
Day14: local sights Florence
Day15: early train from Florence to Venice (2N)
Day16: Venice local
Day17: Back to Milan for evening flight at 8pm

I have decided to do three cities as originally planned, but thanks for all the suggestions. Maybe this trip is a sampler and the next time will be the main course.

I will however do Pisa on the travel day from Rome to Florence as suggested.

What should I do in the two full days I get in Florence?

What should I do in the two full days I get in Florence?

A guidebook is really a necessity. If you don't know what to see in Florence (why did you choose to go there?) you should get one which covers not just Florence but your other chosen destinations as well. In addition to knowing what all three cities have to offer for sightseeing, you'll need to know when those attractions are open and how to avoid very long ticket queues at the most popular. So get a good book and spend some time with it.

As all of our interests and traveling styles are different - traveling with young children involves some different considerations - it's best to choose based on what YOU want to see versus what someone else tells you. Florence is heavy on museums, particularly art, so if you and your family don't enjoy those, you'll want to explore what you might prefer instead.

Maybe that sounded like a clueless question, but I meant to ask for recommendations if any. Like a Siena day trip or a good winery.

Unless you want to delve further into Renaissance Florence with more art and churches, then definitely head to Siena for the day.

Yep, you could do Siena. Or Lucca. Probably better than wineries with an 8 year-old.