16 Days - Paris, Madrid, Rome, Venice Florence

I'm a bit confused about the time you have. If you arrive on the 14th (this means you fly out of the US or Canada on the 13th, correct?) and depart on the 31st, you have 17 nights in Europe. Your Options 1 and 3 add up to 18 nights and Option 2 adds up to 19 nights.

I don't like to backtrack so option three is the only one that makes sense, except for Verona. Paris-Venice-Tuscany-Rome-Madrid. I'd leave out Madrid to spend more time in Tuscany and not lose another day to travel.

Yes. Math is off. We have 17 nights. I would have skipped Madrid if we didn't need to be there for a quick work meeting on the 29th. We leave from there on the 31st.

I see that in some journeys you account for travel by lopping off half a day, but I think you will find long journeys like Paris - Italy will take a lot longer than half a day.

For example, Paris - Rome. If CDG-Fiumicino you have the Leonardo Express, if Ciampino there is no train and although closer in it is less convenient. So say, an hour checking out and last minute stuff like breakfast, an hour to the airport, 2 hours check in, 90 minute flight, an hour for baggage claim and walking though the airport (you have business meetings so I presume a suitcase), and half an hour on the train plus anywhere from zero to thirty minutes waiting for the train depending how your luck rolls, plus 30 minutes to get to your Rome hotel, plus an hour to check in and freshen up before heading into the tourist fray (not counting how long from your hotel to the first tourist stop. So 8 and a half to 9 hours for that 90 minute flight. For long journeys I just give over the day to the relocation.

But on some trips like Siena to Madrid, Venice to Rome, Rome to Madrid, you don't seem to allow any travel time.

I'd be risk averse if trying to mix pleasure and business across multiple countries in Europe, so I'd want to be in Venice on Oct 18 and Madrid on Oct 28 if flying in. But you may feel you don't need to be that conservative for Venice since your first commitment is in the evening.

Monday is a day when museums are often closed (Vatican Museums and some other sights are closed on Sundays), so keep that in mind when laying out your itinerary.

I'd opt for visiting Verona on a day-trip from Venice to avoid one hotel change. It's just an hour by train. However, I'm sure hotels are substantially cheaper in Verona, and being in Verona likely gives you a quicker train ride to Rome (or Florence, if you prefer)--though that depends on when you depart. So which do you prefer: fewer hotel-changing hassles or less train time?

I don't know how much of your time in Venice will be taken up with business meetings. That would affect how many days I'd want in the city.

If you want to see some of the smaller towns you've mentioned (all lovely, of course), I think you need to cut either Florence or Rome to allow enough time in your base cities. I'd choose between Florence and Rome based on whether I had a passion for ancient ruins vs. Renaissance art, and whether I preferred smaller vs. larger cities. I suppose it might be a bit warmer in Rome.

Your trip(s) within Italy will be hassle free and fairly quick since there's fast-train service. Getting from Paris to Italy and from Italy to Madrid will be more complicated as already pointed out, so you're losing a good bit of travel time on this trip. I'd figure Orvieto, Segovia and Toledo are each full-day trips, days which can't really be counted as sightseeing time in Rome or Madrid. I haven't been to Siena and Lucca recently enough to be sure about them.

I'd suggest something like this:

Fri, Oct 14: Arrive Paris (4 nights; only 3 good days due to 10/14 jet lag)
Tue, Oct 18: Fly to Venice (4 nights, or 5 if a lot of work commitments; day in Verona)
Sat, Oct 22 (or Sun, Oct 23): Train to Rome (4 or 5 nights; day to Orvieto if you can tear yourselves away from Rome)
Thu, Oct 27: Fly to Madrid (4 nights; one day to Toledo, one day to Segovia)
Mon, Oct 31: Fly home from Madrid

Hey, I've pretty much reproduced your Option 3!

If you feel both Florence and Rome are musts, I'd keep Venice to 4 nights, trim Madrid to 3 (dropping one of the day-trips), and split the resultant 6 nights between the Florence and Rome based on your interests and what impact, if any, Sunday/Monday museums closings will have on your plans.

Way too many cities for 16 days.

I would say drop Madrid, that will give you more time, but you fly out of there. How do you plan to get from Rome to Madrid?

You need at least 5 days in Paris and Rome deserves 5 as well. Siena and Verona are great, but eliminate them and have fewer cities to visit. Travel from city to city reduces sightseeing.

While in Madrid, go to Toledo, that is a must see. Segovia is great if you have time.

Since Madrid is non negotiable most of your itinerary is already dictated. Paris 5 nights, Venice 4 and then you have to be in Madrid 5 days later. I'd spend the 5 with at least 2 days in a hilltown and then either Florence or Rome before Madrid.