14 to 18 Days Italy and France

My advice, no one-night stops. You won't have time to see anything, you will be travelling both days. Minimum 2 nights, but better 3 nights.
I would drop Cinque Terre, and do Pisa as a day trip from Florence.

What method of transport? I guess fly Paris to Rome (budget airline), and train for the rest.
Where on Lake Como, where in the Dolomites? Travelling between the two will range from difficult to impossible, depending on where you choose.

Where are you travelling home from? Hopefully somewhere easy to get to from the Dolomites.

Thanks Chris!

We are actually coming from SINGAPORE.
Original thought was to fly in Rome and then out of Milan to Paris for the last leg.

What’s there to do at Cique Terre? Like to know what we’ll miss or maybe extend the trip to include it.

It is very helpful to know how many nights you have for your trip. Two nights equals one full day in a location. Travel days are half days, at best as every time you change location you use about half-a-day in the process. So please clarify nights.

Also, try to pencil out what you want or see and do in a location to help determine how many nights to spend there. For example, the Cinque Terre is a hiking location. Do you have to hike? No, but that is what people do there, mostly, and if the weather is bad, there is little to do. Luckily in May, the weather is usually good but it is not a good day trip location so you have to spend at least two nights.

The same with the Dolomites. People go there to hike in the mountains. It is fantastic with amazing vistas even if you do not hike a lot as there are easy walks. But exactly where is important as transportation can take some time and trains do not go into the mountains so you need to use buses. We can help with the details once we know exactly where you want to stay.

Look at proximity so you can take advantage of day trips instead of changing locations. As Chris mentioned, you can day trip to Pisa from Florence.

I would plan 4 nights in Paris, by the way. Such a wonderful city!

You will probably be (certainly at least one of you will be) utterly wiped out when you arrive at your first stop. The combination of jetlag and sleep-deprivation (if yours is an overnight flight) is a killer. So if you plan to stay at your first stop for just 3 nights, you'll really have only 2 days for sightseeing. I, personally, wouldn't go to Paris for just 2 days of sightseeing. You could fly directly to Italy, eliminating one hotel change and one intra-European flight (and the hassle of dealing with two airports).

Plan B:

• Fly into Milan (flights from Singapore to "Milan Malpensa" airport by Singapore airlines). Go immediately to somewhere on Lake Como (example: Varenna, 2 hours from the airport by train)
• Chill out, enjoy the scenery and adjust to the time difference.
• Then do Italy north to south: Venice - Florence (possible day trip to Pisa) - Rome. All by train.
• Fly to Paris (cheap flight on a budget airline)
• Fly home direct from Paris.

Historical note: in the middle ages up to the 1700's Venice was exactly what Singapore is now, an island city state based on sea trade. In this case trade around the Mediterranean. It was stinking rich due to its position on the coast at the mouth of the river Po, which lead inland to the big northern Italian cities. It had a unique advantage, river boats could transport from these cities directly to the factories and merchants along the canals, and sea going boats could load directly and then sail all over the Mediterranean.

Then in the 1700's trade shifted from the Mediterranean to the "new World" and around Africa to Asia, which gave an advantage to countries on the Atlantic coast (first Spain and Portugal, then Netherlands an Britain). And then in the 1800's they invented railways, and Venice no longer had a transport advantage.

I agree with the general drift of the other replies. Fly into Italy and out of Paris or vice versa. Eliminate the Cinque Terre and Dolomites. Add those 4 days as follows: 2 to Paris, 1 to Rome, 1 to Lake Como. Do Pisa as a day trip from Florence. If you get tired of Rome or Paris (hard to imagine), there are tons of day trips you can do easily. Both cities are saturated with history. Your son should be in heaven. Como can satisfy your desire for gorgeous mountain scenery; different from the Dolomites, but stunning nonetheless.
You really will have a more satisfying trip if you cut down on moving around.

Thanks everyone! Really appreciate the inputs. Will definite heed the advices.

Btw, any tips on where to go in Rome and Paris?

There are a number of wonderful places to go in Rome and Paris! It would be a great thing to start looking at why those cities interested YOU, as we all have different interests. A guidebook would help, and when you are trying to determine whether you have enough time to fit everything into your schedule, don’t schedule more than one major sight per segment of the day (morning, afternoon, evening) and sometimes that is even too busy.

For Paris, take a look at this pass. It will save you both time and money.

http://en.parismuseumpass.com/rub-t-price-36.htm

Rome is a little tricky, since you need to know the cost of each site and you only get 2 free with up to 50% on other sites. But it does include city busses and metro. The key is to use the most expensive sites first.

http://www.romapass.it/en/FAQ/

List of fullprice & discounted sites.

http://www.romapass.it/files/doc/SitiAderentiCostoBiglietti201809_eng.pdf

Florence has a pass too, the Firenze Card but At €85/72 hrs, it's hard to get enough sites in for it to make it pay for itself, but the skip the line feature may make it worth it for you.

http://www.firenzecard.it/index.php?lang=en

As for your itinerary, add as many days as possible.

This path works well transportation wise as well as alternating large cities with quieter scenic areas.

Arrive Rome. With a 13-16 hour flight, you're going to be cranky, tired or both. Check in, wander a bit, have dinner and go to bed. This day is basically wasted and that may carry over to the next day.

5 Nites Rome.
A good day trip is Orvieto.

Day 6. Train to Cinque Terre. 3hr30m.

3 nites Ct.

Day 9. Train to Pisa 1hr38m. Drop luggage at station, bus to Piazza Dei Miracole. Bus back to station, pickup luggage, train to Firenze SMN 1hr.

4 nites Florence.
Good day trips, Siena, Bologna, Pistoia.

Day 12. Train to Varenna. 3 hr42m.

3 nites Varenna.

Day 15. Train to Milan Malapensa. 2 hr.
Flight to Paris Orly, check Easyjet and Alitalia.
1hr25m.

4-5 nites Paris.
Versailles or Giverny if you need an escape.

If you prefer the Dolomites to Varenna. Use this version from Florence.

Train Florence-Bolzano. 3hr11m. From here it's a bus ride to Ortisei.

https://www.val-gardena.net/en/questions-and-answers.asp?id=244

3 nites Ortisei

Train evening. Bolzano-Venezia 2hr39m
1 nite Venice or at an airport hotel.
Fly VCE-Paris Orly. 1 hr45m.

For suggestions on where to go in Rome and Paris, be sure to get input from everyone in your family. My husband and I went with our two adult children once and we had multiple family meetings trying to decide how many days to spend in each of several cities. What worked for us was to ask each person to bring three suggestions to the table and try to arrange it so everyone got to see at least one of their choices. It's also possible to split up on some days and go in different directions.

I agree with the suggestions to add time to Paris and Rome. We spent 9 nights in Paris and 8 in Rome, and we never ran out of things to do. Four nights in Florence should be good. I'd omit one of the other locations in order to add to Paris and Rome.