Itinerary Check Milan/Lake Como/Venice/Florence/Rome 10 Days

I'd personally find this too much moving, but everyone is different. Have you traveled before, and does everyone have the same expectations?
I'd remove Milan and the Menaggio excursion in favor of more time in Venice, Florence, or eliminate one of those if you would rather keep them. This is just very subjective depending on one's energy level, etc.

I stopped for gelato in Lugano. I would stop there for gelato again, and that's about it. The overland drive to Menaggio is cool (old smuggler's route) but really not worth doing what amounts to 3 days in that region. And I love Lake Como. Beyond that, this is a hectic pace. Do your day in Milan, catch the morning train to Venice. Add one day each to Venice, Florence & Rome. You will be glad you did.

Skip Lugano and go directly to Menaggio on Lake Como. We always rent cars in Europe but never for Lake Como where we have stayed four times. You can hire a driver or use public transportation to get there.

I'm afraid this trip is going to much more rushed than you are imagining and may not be memorable in the way you hope. You have allowed less than 24 hours in Venice, less than 48 in Florence and about 60 in Rome (really just two full days there). Every one of those time allotments is way shorter than I'd recommend.

I haven't been to Menaggio but do like Lugano and that part of Switzerland. I've been there two or three times (though not recently). In this case, however, I really, really question the decision to spend two precious days heading north to Switzerland when it means cutting the three major Italian tourist destinations so short. I don't know how much time you'll spend dealing with the car-rental agency twice, but it will not be no time at all.

If you do go up to Switzerland, be sure to get the necessary highway vignette and place it properly on your car. I think it costs 35 or 40 Swiss francs. Without it, you aren't allowed to use any of the highways.

I'm not sure a morning is even long enough to see both St. Mark's and the Doge's Palace; at the very least, you will be very rushed. You'll only have a little time late on the day you arrive to try to see a bit of the less touristy Venice. The area around St. Mark's is a nightmare (though worth braving in order to see the church and the palace). Where are you staying in Venice? The most convenient area for your sightseeing activities is quite a trek from the train station where you'll arrive and depart.

If driving, I would first drive to Menaggio and have a trip to Lugano the following day. This because if you drive Milano to Lugano you are likely needing a Swiss highway sticker, that is SFR 40.- ; but if you drive Menaggio to Lugano you just tell people at the border control that you are just going to Lugano, not traveling on highway and so you do not need it.

(There are two possible ways to skip the sticker from Milano to Lugano; first, your car already comes with the yearly Swiss sticker; second, you drive only ordinary roads, possible but not easy to navigate.)

You are obviously a good planner, but like many new travelers, have planned too much.

First glance, I really don't see any down time. Two nights in one place really equals one day. I don't think you're estimating your transit time accurately, and the time to check out, get to the train station, find your platform, and repeat at your destination. Also, with the post- COVID flight chaos, there's a greater chance of delays/ canceled flights, which would really impact your first day. What if you didnt get into London that first day, so missed your Milan flight? That happened to me. And why one night in London? You're going to deal with airport security and possible days again? That's just too much work for no fun in that 24 hours.
Less than 24 hours in Venice? I'd suggest a minimum of two nights in Venice. Overall, I think you need a minimum of 12 nights on the ground in Italy. Remember at home, you have weekends to move slowly in the morning and change your pace.
Have you checked if you can take your rental across the border to Switzerland, and that you need a vignette? Also, why Lugano? Have you considered the Bernini Express route back to Italy.? European trains are very efficient and user - friendly, especially taking into account gas prices, tolls, and parking fees.
There's a wealth of info here, so review some of the posts under the Italy section, and do Search of previously posted itineraries.
You are going at a great time, and have a wonderful trip.

Thank you all for the suggestions, I am aware that it is a lot to see and do in 10 days. This is our first ( but definitely not last trip to Italy) London is just a connection (4 hour layover) and Milan is just a start point. Lugano is a day trip request by the group on our way to Lake Como. Which is really 1 full day.
The short time in Venice is unfortunate, but we are staying near St. Marks square and will see what we want to see. The tour we have in Venice is 2 hours.
Our rental in Florence is near the uffizi and the rental in Rome is near the colosseum. This is not an in depth study , but rather the highlights. I am an architect and have studied all the buildings and monuments, their architects, artists, patrons and their importance in history extensively.

Looking at rental car prices for late September, it looks like you will end up paying $400-$500 for a 3-day rental of a mid-size car large enough to be comfortable for 4 people plus luggage. Plus gas and any fees required.

I suggest you skip the overnight in Milan, and take a car service from Linate directly to Menaggio. This company charges around €225 for a comfortable 6-pax van for the trip.

https://city-airport-taxis.com/airporttransfers/reservations/taxi-from-Milan-Linate-Airport-to-Menaggio?single=1&loc1_name=Milan+Linate+Airport+-+Italy&loc1=245&loc2_name=Menaggio+-+Italy&loc2=558&pax1=4&date1=15%2F05%2F2023&date2=05%2F04%2F2023&quote=1&time1=12%3A00&time2=13%3A00

To return to Milan, you enjoy a ferry ride across the lake to Varenna, where you catch a train for the 1-hour ride to Milano Centrale.

Skipping the night in Milan will give you one more night to spend in Venice. Still not enough, but better than the 20 hour visit you have planned.

I have a midsize for $300 including taxes. i am aware that i might have to add the vignette if it not already on the car.