Possible itinerary

You could certainly do as proposed. People will offer a hundred different options (stay in Spain, drop France, drop Switzerland, etc) but in the end, you have to make you happy, not follow someone else's itinerary.

At most, stick with what you have. The big problem is distance, especially from Madrid to the area of the other three stops. I would look into a budget flight, Madrid to ? Maybe Marseilles, Milan, maybe a Swiss airport, that will cut the big travel day to 4 to 5 hours, between the flight, security, etc. Otherwise, a train from Madrid to Avignon would take 10 to 11 hours. The other hops should be a half day or so by train.

Milan (or Turin) would also work, then do a loop, up into Switzerland, down through France, and into Italy. Rather than the traditional Switzerland spots (The Grindelwald area) You could look at the region on the Italian and French side of the alps, shortening travel a bit. Depends if you want "Switzerland" or just mountains.

An addition: Skip Barcelona, if you add days there, then you might as well stay in Spain. Also, where will your Daughter be studying, that might change things.

I feel like you are missing the best parts in Spain and Italy. Also, with those locations, I think you will indeed spend lots of time traveling from one location to another. But, your start and end days are firm, so ??

My suggestion would be to leave Madrid immediately and go to Barcelona, possibly by train (stay 3 nights). From there, fly to Marseille or Aix or ??(stay for 3 nights), Fly to Zurich. From there, a gorgeous train ride thru Switzerland. The Bernina Express begins in Chur. So you could land in Zurich immediately train to Chur, for the night. Take the Bernina Express and stop for a night along the way in St. Moritz, Pontresina, or wait until after Bernina train ride to stay, maybe Varenna or Lugano? and then head to Milan.

You are going to get a ton of responses with vastly different ideas. I really like the train idea thru Switzerland. It would be a lovely introduction to Switzerland.

We often travel at more of a clip than many on the forum. Key would be to have well organized, carry on luggage only. Plan each city with your choices of sites prior to the trip--opening/closing hours, what to see, transportation to and from sites, restaurant choices, walking tour maps.

Your plan will waste a lot of time and money on traveling. Trying to cover way too much. Spain is wonderful and you could easily spend the entire 10 days there and still not see a fraction of that country.
For example, near Madrid are two wonderful cities that you can do on day trips. Toledo is the former capital 500 years ago and very special. Segovia is on the other side of Madrid and has an intact massive ancient Roman aqueduct as well as other great sites.
Buy a guidebook and do some research on what to do.

I have been to all the places that you mentioned and enjoyed them all. Travel in Switzerland is slow by car. Switzerland is one of the most expensive countries in Europe, but the vast mountain scenery is great. Suggest you visit Lucerne and the area around Interlakken. You could easily spend all your time outside Madrid in Milan and Switzerland.

I realize hat you may have already purchase your air tickets, but you can still reduce your travel to some degree. The Provence area of France is loaded with great places to visit, but you will need more time thee. 1 Night in Milan is short. Have you checked on how much time it will take for you to drive a rental car or take trains? Be aware that if you rent a rental car in one country and drop it in another, that you will have to pay a huge drop charge.

Yes, you could do all this but you only have 9-10 days. The first night follows a day consumed by travel/jet lag. How long would it take to get from Madrid to Provence? Presumably you're flying, but even then, once you land in Marseille or Nice, will you get a car? Where will you head? Or will you stay there? Realistically, that switch is going to take most of day, meaning you lose another night without seeing much. From Provence to Switzerland, again by air? will take another half day and up to a full day, depending flight schedules and on where you are going once you get to Switzerland. This eats up another night without seeing much. From Switzerland to Milan will take 1/2 day, unless you're going by train, which will take longer. And then there's the morning/afternoon you leave Milan for home. Probably won't be able to do much that day. I'm getting 4 nights after travel days with little to no sightseeing payoff. Add in time for your arrival/check in, unpack/pack/transportation in each city or region, and eat in each city, and what's left? When you do the math, to me it looks like you will be spending a lot of in motion with little payoff. Back up to your original plan for 3 or 4 cities/regions. Not knowing your family's interests, it's pretty hard to recommend any must sees/dos. I'd spend days in a museum, for example, others wouldn't bother going in at all - they have other interests.

Have you researched each destination? Based on what you've read, what's your first choice? Your second? How about your daughter's choices? What are your must-sees for each city or region? How long will that take? I get wanting to see as much as possible during your trip, but all the travel time you'll need seems way more than it's worth to spend such a short time on each stop. Maybe changing up the order of your preferred stops could save you a little transportation time, but you'd have to check combinations of flight and/or train schedules to do that.

In the end, I'd say can you prioritize your locations and maybe pick only two? Personally, I'd pick one, but we're slower travelers. You clearly are not, but I can't help but feel the trip will be more of a disappointment than not if you try to pack this much into such a short time.

If your daughter is studying abroad, she probably has places she is going to see on some weekends, so I would skip those on this trip. If your flights are already purchased, you still could do a cheap airline inside Europe, so you still have lots of options.

I move locations often during my independent trips, so I’m not against multiple locations. But, I am very stingy with my time. I don’t average more than an hour or two in transportation time between cities, and I pack extremely light & am crazy organized. The reason I’m mentioning this is because your travelers need to have an honest look at your habits before making final plans. Is someone slow-moving in the morning or a heavy packer or unorganized? Those will eat into this very short time you have. If so, cut your locations down, enjoy wherever you are. Taking four hours to get to the next location will feel like you remember the train or car more than the wonderful sites.

Personally, if I had to solve this puzzle, I’d fly from Madrid to either Zurich or Nice on Day 2 or 3. Then focus on either Switzerland/Italy or France/Italy. Even then it’s a very tight schedule with so much to do & narrow down.

auconyers,
Regarding your transfer days, whether you take a train, fly, or drive, don't forget to calculate the time it takes to check out of your lodgings, get to the airport/station/car rental location, arriving in the new city and locating your hotel, finding parking or getting from the airport or station to the hotel, and checking in. Based on your distances, there may be a full day taken up in moving.
Your 3 nights in Madrid, of course, means two days visiting the city. Likewise two days in Provence, one day in Switzerland. The suggestions to perhaps reduce your locations are not meant to rain on the parade, rather to enhance it. Check a map of Europe or check online for distances and plane/train times to see what is feasible. And re the sites that tell you drive times, add an hour or two to them because they don't factor in gas/food/comfort stops or traffic tie-ups. We use viamichelin.com regularly when we drive in Europe and always need to add some time, unless the distances are very short.
Have fun in the planning as well as the traveling!

Stay in Spain and Italy, Drop France and Switzerland entirely. Spend 10 days between Madrid (with side trips to Toledo/Segovia) and Milan (maybe with a short hop to an Italian lake region like Varenna or Lake Como). Take a budget flight from Madrid to the next destination (e.g., Marseille, Milan, or a Swiss airport) to avoid a wasted day on the train. Focus the remaining time on the two most desired locations (e.g., Provence and a shorter visit to the Alps).

Thank you, already getting great feedback, which is what I need to help determine the best plan.

Just to clarify, we have been to Italy several times, absolutely love everything about it, and spent 3 days in Milan last year, so not trying to spend additional time in Italy on this particular trip other than the fact we need to get our daughter checked into her place in Milan before we depart.

Sounds like my initial thoughts are trying to squeeze in too much. Hate to miss something if we’re so close, but it’s always nice to have an excuse to return!

So, backing up….arriving in Madrid, departing from Milan, spending 1 night only in Italy, due to the fact been there several times, but have never been to Spain, Switzerland, or southern France, what would y’all recommend for a 9-10
day itinerary?

So, basically, to repeat my above post. Arrive Madrid, stay in Madrid or immediately train to Barcelona, either city for 3 nights. Then plane to south france, stay 3 nights. Then plane to Zurich and spend two glorious days on the Swiss railway. From Zurich, immediately take the train to Chur and stay 1 night. Then take the Bernina Express that ends in Tirano, Italy. You can stop during the Berina train route at St. Moritz or Pontresina for the night, finish Bernina Express the following day and head to Milan. The Bernina express is one of the great train trips in Switzerland. HIGHLY recommended.

Honestly, I've seen a lot of faster, rushed trips than I have outlined here. A few years ago, we had a planed trip to Italy. Airfares, for us, were quite high. It was a fair amount cheaper to fly into Zurich. We then took the train ride as described above and ended in Varenna, Italy.

Two nights in Switzerland is not enough to see the country properly. You should drop Switzerland from your itinerary. 3 nights in Provence is too rushed. I suggest you drop Provence from your itinerary too.

With just nine nights on the ground, if arriving in Madrid and leaving from Milan is definitely fixed or if you already bought your plane tickets, these are the only two cities you have time for. If you want you could add in some place near Milan in Northern Italy.

If you can change your departure city, a better plan would be to just split your time between Madrid and Barcelona. Can you spend 4 or 5 nights in Madrid and the rest of your nights in Barcelona, arriving in one of those cities, leaving from the other, and taking just one train ride from one of those cities to the other? Another good plan could be, just spend all your time in the Madrid area, including one or more day trips to Toledo, Avila, Segovia, and/or Salamanca. Less is more; don't try cramming every place you listed into one 9-night trip.

@Mike, OP is saying they've been to Italy including Milan. Needs to get an adult daughter to Milan by a certain date. Milan and Italy are not a priority for the trip they just need to end in Milan.

They could drop Switzerland, and fly from Southern France to Milan.

With that amount of time, they are not going to be able to thoroughly see any of the places on their list. However, there is nothing wrong with getting a taste of a place. Just as long as they are not spending more time on trains than they are sightseeing.

I have four adult kids and we've had many "trips" that were more of a task to help the kids or get them somewhere. Then we tried to build a little sightseeing around the main task/objective.