May-June 2016 Trip Planning

Fly to Venice (3 nights)
Train to Florence (4 nights) with day trips to Siena and Lucca+Pisa
Train to Naples for Amalfi Coast (4 nights) with day trips to Capri, Positano, Pompeii
Train to Rome (4 nights)
Fly to Paris (4 nights)

or

Fly to Venice (3 nights)
Train to Florence for Tuscan country location with car (7 nights)
Train to Rome (4 nights)
Fly to Paris (5 nights)

After Venice, Florence and Tuscany/Umbria, you could fly to somewhere in France, for example to Geneva from Florence, rent a car and spend 3-4 days driving to Paris, then the rest of your time in Paris. If you are spending 5-7 nights in Tuscany/Umbria do you still want 4 nights in Florence?

Here's a tip - go to the wikipedia page for each airport. There's a chart listing every airline that flies from that airport and all the destinations they fly to. There are airports in Pisa, Florence, Bologna, and Rome. All would be fairly close to your places in Italy.

Or simply fly to Paris. You could explore any of the areas nearby for 3-4 days - Loire Valley, Normandy, Burgundy.

Thanks for the suggestions. I'll start looking into the France part of the trip and see what we would most like to do.

OK - this is an plan I'm considering .. most of the lodging will be apartments that sleep 4 (for the 3 of us).

Depart PDX on 5/20/2016
Arrive Venice (probably 5/22-24) (2 nights)
Florence (3 nights) (5/24-27)
Cortona (3 nights)5/27-30) (rent a car in Florence and maybe return it in Rome or possibly keep?)
Rome (5 nights) (5/30-6/4) (several choices of places to stay in the city)
Paris (7 nights) (6/4-6/11) The house I found is in a suburb, but we could get into central city in 20-30 minutes on Metro and it’s 10 minutes from airport. We could rent a car for day trips to various places outside Paris.
Fly home Paris-PDX 6/11

Having a car in Rome and Paris? Forget it !!
Not only a nightmare with traffic and parking, but you just don't need it.

You are staying just in cities, so a car is not a good idea, especially in Rome and Paris, which are dreadful even for the most confident of drivers.

With jet lag, you need more than 2 days in Venice. Moving on each time will cost you half a day.

Your revised itinerary is confusing. You show departure on 5/20 with first night as 5/22. We also fly from the west coast, and arrive the next day, not two days later. So, first night would be 5/21. Also you're showing 5/24 in two different places. I find it best, when planning, to list nights only. That way I know where I should plan my lodgings.
If you allot a week to France, just in and around Paris, you'll still have two weeks for Italy. IMO, that's reasonable; especially if you eliminate Rome. There's plenty to see and do in the areas around Venice and Florence. One possible plan would be:

5 nights Venice, with day trips to Padova, Verona, or even Ravenna
4 nights Florence, with day trip to Siena
5 nights Tuscan countryside, one base, endless possibilities for day trips

There are airports in Pisa and Florence. I'm quite certain you can find cheap flights to Paris from one of them, or the reverse.The other thing to be sure to do is to book open-jaw flights, PDX to Italy (Venice or Milan, if Venice is impractical) and Paris to PDX . It might, in fact be easier to make Paris your starting point, and fly to Venice from there. You are acquainted with skyscanner, kayak, etc.?
As you get more into specifics, you can easily tweak the above plan, adding a day here, subtracting a day there. Just don't make any non-changeable reservations until you have figured out the whole picture.

The confusing thing was I added checkin and out dates.. so yes.. the 24th I'd check out of one spot and into another. I feel like 9 days in Tuscany area is too much given our interests in other places, and we knew we were going to shortchange Venice, but thought we could get a taste of it. Depending on when our flight leaves PDX we'd either arrive in evening of next day or morning of two days I think.. based on what I've seen.

To simplify this a little, however...

Depart PDX on May 20th
Venice (3 nights)
Florence (3 nights)
Cortona (3 nights)
Rome (5 nights)
Paris (7 nights) (departing Paris June 11)

Maybe should add a day to Florence or Cortona and remove a day from Rome? I was looking at it as 6 nights in Tuscany/Florence. We weren't thinking of skipping Rome in this plan.

In Paris we would like to do Giverny, Chartes, Versailles, and Paris things.. several museums and overall sights and gardens etc.

As for cars.. I really don't plan to use a car in the cities at all.. mainly only in Cortona. I would rent the car in Florence and either return it to Florence and train to Rome.. or drive to Rome and drop off there. thoughts? I need to figure out housing in Paris. Public transport is fine.. but figure staying in Paris metro for the whole 7 days makes the most sense. If we had free parking (such as staying in a suburb), I'd consider a car to be used for day trips only.

Thanks for any thoughts.. Much appreciated.

Some thoughts on your time in Tuscany after Florence, if you have decided on Cortona.
Day 1 - Drive via Siena (or Chianti) to Cortona
Day 2 - Excursion to Montalcino + Montepulciano
Day 3 - Excursion to Assisi + Gubbio
Day 4 - Pinch a night from Rome for an overnight in Orvieto (returning your car here)
Day 5 - Rome by train

hmm -- nice idea about staying a night somewhere on the way to Rome. Yes, that sounds pretty good overall, and I really do think we should take a day from Rome. It will probably be overwhelming.

So updated plan is:

Depart PDX on May 20th
Venice (3 nights)
Florence (3 nights) pickup car when leaving town
Cortona (3 nights)
Orvieto (1 night) and return car
Rome (4 nights)
Paris (7 nights) (departing Paris June 11)

In Paris, if you are looking at making the following day trips by yourself ..
Giverny/Rouen - Trains from St Lazarre station
Chartres - Trains from Montparnasse station
Versailles - RER line C (yellow) from stations along the Seine

I would suggest searching for accommodation in St Germain des Pres near the metro at Solferino or Rue du Bac.
From here metro line 12 (green) takes you to both St Lazarre and Montparnasse stations.
It is also a short walk to the Musee d'Orsay station for RER line C (yellow) to Versailles.