10 Days in Lugano, Milan, Pisa, Rome, Florence and Venice

It's too crazy in my opinion. If you want to proceed, I would suggest looking into flying from Munich to Milan because those cities are 8 hours apart by rail. I would also recommend flying into Munich and out of Rome or vice versa. Flying round-trip from Venice makes no sense for this itinerary.

More generally, I would suggest refocusing your idea of what you want this trip to be: Italy or Germany? I would also suggest you take a good look at rail schedules to give yourself an idea of how long it takes (and costs) to get from one city to the next. Also keep in mind that changing cities eats up about 1/2 a sight-seeing day.

ETA: Finally, I suggest getting guidebooks to help you understand what your sightseeing options are in each city.

What travel guide book do you have? There is no way you should try to do all your organizing like this as many of the answers are in guide books and you need to see the maps of where your destinations are located

To answer your question, "Is this too crazy?" using your words with only a puncture mark change, 'This is too crazy!'

Looks like an audition for 'The Amazing Race', not a vacation.

If you are coming from the US and have someone with you, you may be subject to prosecution under the "cruel and unusual punishment' clause of the Constitution

You really need to make a map of what you are proposing and the do 'searches' for travel from/to all your destinations to see what logistical hurdles you have.

Let me be one of the many (Edit: but not the first) who will probably comment that you have too many stops for just 10 days. We will assume you found a good price for a round trip into and out of Venice. This is leading you to have to backtrack on your trip. (It looks like a "multi city" ticket into Munich and out of Rome might have worked better.)
You should probably drop a couple of stops. (Lugano / Switzerland and Milan & Pisa are my picks)
Arrive Venice take train to Austria/Innsbruck area. for Night #1 9/18.
Or take a plane to Munich right after you arrive in Venice. .
Then arrive in Munich for your schedule as planned. Nights #2, #3 & #4 9/19 & 9/20 9/21

Skip Milan and Pisa and go to Rome (flying would save a lot of time on the train)
Use those days add a time in Rome, Florence or Venice as you choose.

Take a train Rome to Florence.
Take a train Florence to Venice.

These and the suggestions others will pass along to you may cause you to adjust you schedule. It is your vacation it is up to you to choose your sights.

A common refrain this sight passes along to those who ask questions is......Slow down and enjoy and really see the sights. You will be back....to see the sights you had to pass up this time.

(Edit: Many good thoughts and suggestions from those who answered you before I finished writing my response. And there will be more to follow.)

Some more input from you would be helpful to us..
Where are you flying to Europe from?
And what airline are you using? (Have you already purchased your plane ticket?)
What is your full flight schedule?

I don't mean to be a wet blanket but you ask "What do I see in Lugano, Munich, Milan, Rome, Florence and Venice?" Why would you plan to visit those cities and have such an excruciating schedule if you do not know what you want to see?

Going to Lugano just to say you have been there is a waste of time and money. As others have said, too much for 10 days. Munich and Venice alone could fill your time. Or just Italy: Rome/Florence/Venice. Not even time for side trips IMO.

Thank you everyone! I am flying in and out of Venice because of the price of tickets. I looked at multi and flying into Munich but they were 2 times more if not 3 more. I was going to go in a circle, Land in Venice, train to Innsbrook Austria for the night, Train to Munich for a few nights, Train to Pisa, one night, Trail to Rome a couple days, Train to Florence for a couple days and then the last train to Venice for a couple days. I thought we could "see" more of Europe on train. I can/will look at flights too. The main reason of this trip was to meet some friends from high school for Oktoberfest for 1-2 nights and then we added extra days because my husband wants to see Italy. My husband, my daughter and myself are going on this trip. We will have to take a trip back because she still wants to go to Paris and my husband and I have already been there. My daughters ex lives in Lecco and he suggested to stop in Milan. I have my flight booked already and hotels, the hotels are refundable. I don't want to change my hotel in Munich because there are not many hotels available, the price has gone up or as close to the festival. I appreciate the tips, help and comments.

To summarise your plan....
Land in Venice on the 18th
Lugano on the 18th
Munich on the 19th
Neuschwanstein on the 20th
Oktoberfest on the 21st
Milan on the 22nd
Pisa on the 23rd
Rome on the 24th & 25th
Florence on the 26th
Venice on the 27th & 28th
Fly out on the 29th

This is just way too much, especially when you consider your train travel times ...
4hr 21min Venice - Lugano
6hr 45min Lugano - Munich
7hr 11min Munich - Milan
3hr 08min Milan - Pisa
2hr 56min Pisa - Rome

Can't even imagine that much traveling and moving around in just 10 days. You need to eliminate some destinations.

Something like this would be much more manageable. No connecting trains, and shorter travel days.

Sep
18..Arrive Venice. Train to Verona (1)
19..Train to Munich (3)
22..Fly to Rome (3)
25..Train to Florence (2)
27..Train to Venice (2)
29..Depart Venice

I don't know what's your budget like, but that itinerary will probably be expensive. Munich to Milan I know it's somewhere around 40 euros, Milan to Florence is around 30 euros, 40 euros from Florence to Venice, more 30 euros from Rome to Florence, 27 euros if you pick the Bayern Ticket to go to Neuschwanstein, and that's not considering the tickets to Lugano and from Lugano to Munich, which I never researched, but, considering it's Switzerland, I'm sure it'll be expensive as well. I know budget is less of an issue if our local currency is strong, but, even with this, you don't need to spend unnecessary money on moves that'll limit your resting time.

I know it's a temptation to go to Switzerland just to say "Another country", I'm feeling the same on my planification, but try to think: are you willing to spend a reasonable amount of money and devote a good half-day in transit just to quickly see a tiny part of other country, which you don't even have a specific reason to enjoy?

If I may, try to focus your itinerary on what you want to see. Maybe my desires and hobbies are completely different from yours (I don't have even the smallest desire to go to a place focused on scenic views and nature, for an example, while you can have absolutely no interest in seeing some old stones gathered around), but I can point the best connections. Both of your flights are in Venice, so you need to go to places connected to Venice, in a quick and cheap way. Why not begin your tour there? Again, I can't say how many days should you devote to Venice (you want just to see the historical heritage? You want to be able to spend a day just strolling through back alleys?), but I think you should begin there. After Venice, I think you should venture either south (train to Florence, to Rome, back to Venice) or north (Milan, with a quick stop in Verona, then to Munich, then back to Venice. More expensive, but you can check another country, or even 2 with a day trip to Salzburg). I can't help you with Switzerland, since it was never on my travel plans, so I never researched about it, like I said.

Obviously, I can't propose a perfect itinerary, I never traveled abroad, while this forum is full of experienced travelers, so definitely use their advices more than this one I'm writing, but, if you follow the options I said above, you could fall in either one of those two:

NORTH
Arrival in Venice
Venice
Venice
Verona or Milan (I don't know how a day trip to Lake Como works, so I'll not say anything about it)
Milan (DB overnight bus to Munich)
Munich
Munich
Day trip to Salzburg, Neuschwanstein Castle or Nuremberg
Travel back to Venice (the train is 2 hours faster compared to the bus, but 40 euros more expensive on regular fares, so...)
Departure from Venice (sleep in Venice in order to avoid a desperate rush to the airport)

SOUTH
Arrival in Venice
Venice
Venice
Florence (2h by train, 4h by bus)
Florence
Day trip either to Pisa + Lucca or Siena
Rome
Rome
Rome (depart after 7PM to Venice, to sleep there)
Departure

That is nuts! LOL Ok, I guess I won't do a crazy itinerary. My husband came up with this:

18th land, Venice all day
19th Venice
20th fly to Munich early, shopping, Oktoberfest
21st Munich, Castle, Oktoberfest
22nd train to Milan, early
23rd Milan
24th Florence
25th all day in Florence and late train to Rome
26th Rome
27th Rome
28th, Rome all day then late train to Venice just to sleep
29th Fly Home
Does that look better? So now, best flights to get to Munich from Venice, What trains do I take, do I need to reserve them now? Where do I book the trains? Is a pass necessary? Should I get tickets to see the things we want to see? Good places to eat? Anything neat off the path? Like hidden treasures?

I just googled something on Switzerland, if you want to spend your 10 days in the vicinity. As I said, I never researched Switzerland in depth, so this may have some things (or a lot of them) undoable, so wait for a seasoned traveler to ratify this (or not), but I think something like this could work (although it would be expensive. It's Switzerland, they made their fame on expensive things)

FRANKS AND ALPS
Arrive in Venice
Venice
Venice
Milan
Luzern
Luzern
Luzern
Zurich
Zurich (flight to Venice)
Departure from Venice

Again, I don't have any kind of expertise in Switzerland, so I can't even point day trip options, so take this itinerary with a huge grain of salt, but it seems doable. If you want to check countries down, Zurich to Liechtenstein apaprently is not a big effort (but you would need to cut either one day in Luzern or Venice). I don't know about Interlaken, but it seems the city itself is just a base town for the real gems, so you could trade Luzern for it, or you could use Luzern to go one day to Basel...I'm sorry I can't help you any further.

According to Rome2Rio, the time difference between the train and the bus is marginal, only 50 minutes. So, I think you could consider using DB Bus and save a couple of euros: https://www.bahn.com/en/view/offers/bus/milan-munich.shtml?dbkanal_007=L04_S02_D002_KIN0060_NAVIGATION-LINKS-MAILAND-MUENCHEN_LZ01

I know people want some comfort, but I don't think something from Deutsche Bahn will be made of rust. But I also know my quality pattern usually are smaller than the majority of people, so I'll not say "Take the bus". Just check the possibility.

Also, if you want to visit other countries, why not drop Milan and include a day trip to Salzburg, from Munich? Milan has a lot of beautiful and famous sights, yes, but maybe Salzburg would be a nice fit, too. Dropping MIlan, you could use one day to go to Salzburg and the other half day to go to Pisa, from Florence.

Advice from posters on this forum will mostly be about what they enjoyed doing/seeing. Very good advice, but perhaps not suited to your group, specifically. You need to get a guidebook for Europe or watch some videos to figure out what you want to see. One thing to consider: add a night to Firenze and visit Pisa as a half-day trip from there, save one packing/unpacking/checkout/checkin.

Your latest itinerary is still too rushed. One train or plane delay could start the dominoes falling.

If Munich is the furthest north of your desired destinations, and Rome the furthest south, then you will note that Venice and Florence fall on the line in between, while Milan does not. For ease of logistics, and to save time, take a flight between your 2 extremities, Munich and Rome. With your limited time, I'd ditch out of the way Milan. See my suggested plan above.

Even with the revised itinerary there is something you might want to consider. Moving from one place to another almost always eats up more time than anticipated. It includes packing up time, checking out, getting to the train station /airport, the train / plane time itself, finding the new hotel, and then checking in and unpacking. I'm sure you want memories of things other than train stations, airports, and taxi rides. Don't mean to be Debbie Downer, just something to consider.

Does that look better? So now, best flights to get to Munich from
Venice, What trains do I take, do I need to reserve them now? Where do
I book the trains? Is a pass necessary? Should I get tickets to see
the things we want to see? Good places to eat? Anything neat off the
path? Like hidden treasures?

Definitely better but you should also skip Milan this trip. It's a fine city and has its attractions, but for a first time visit to Italy, your time may be better spent in Rome or Florence. Skipping Milan on this trip will give you more time to find hidden treasures in Rome and Florence. I would add the Milan time to Florence. From Florence you can do a day-trip to a classic Tuscan hill town such as Siena, San Gimignano, Volterra, etc.

I see in your husband's revised itinerary that you would only be in Florence on September 25th. We are there the 24th and 25th....be aware, the 25th is Monday and the Uffuzi and Accademia are closed that day. Those are 2 of the biggest attractions in Florence. Just an FYI.

Edit...sorry...I see the 24th now. Make sure you do those attractions on Sunday. We will be there also!

Thank you so much for all the tips. My husband made a schedule and I'm gonna look at the variables. I booked hotels but I can cancel to rebook them too. I hope to book the extra airlines tonight and get what we want to do each day and see what helps. We are used to traveling and are pretty quick packing things up. I figure the trains can give us time to relax. I'm just hoping my back and energy holds up. I had a major back surgery at the end of February. I am positive my complications resolve by then. I should be finished with PT will be done by August. Surgeon said to walk a bunch!! :) I think I've got that down. :)

'''We are used to traveling and are pretty quick packing things up.'''

Getting your stuff ready to go is only one part of moving from place to place. While trains run fairly frequently, its not the same as walking out of your motel room and hopping into to your car. You will need to check schedules to see when they go to where you need to go.

With your time constraints, I agree with the suggestion to skip Milan and add that time to somewhere else.

This may be a repeat of advice mentioned previously, but if at all possible, put all your days in Venice at the end before your flight out

We had a wonderful trip! Thank you for your suggestions! We flew into Venice on 9/18, took a water taxi to "Venice" and checked into our room. We then went to explore the city before it started to rain. We had some great food, took a gondola ride and walked around and took the sites in until late that evening. The next day we went and explored again. My husband didn't want to get tickets for anything in Venice and by the time we were bored, everything was sold out. The next morning we woke up and took the train to Munich. It was a wonderful trip. I loved to see all the scenery. We arrived and checked into our hotel. We got ready and went to Oktoberfest but went to a tent and got a table that didn't have wine so I wasn't very happy. :) My daughter wound up getting lost and we had to go get her and didn't get back into the room until 3am so we had to cancel our plans to see the castle the next day. I was bummed but we will go next year. We walked around the city and then headed back over to to Oktoberfest and went to a tent and got a table that did have wine!! It was a wonderful time and we met some great people! We flew out the next morning to Milan, saw everything we wanted to see there, took the train to Florence, saw everything we wanted there and then off to Rome. The history and art was amazing! We saw so much it was amazing!! We headed back to Venice to hop on the plane home. We saw just about everything we wanted to see, had a wonderful time and really wouldn't have done too many things different. I wish we could have shopped a little more and added 4 more days to have gone to the coast. We are planning on going back to Oktoberfest next year and I think we will do Switzerland. :)