Flying into and out of Milan August 6-19

This sounds pretty good and congrats, btw!

Consider that you will be tired from flying to Milan, then getting to train station, then going to Venice. A long travel day. Venice is such a unique city I would spend another day and night there as the first night you will probably be exhausted. Also, you traveled on day 1, then again on day 3? You might want more of a break.

Take one day from Tuscany or Rome, and you will still have plenty of time to relax.

Going back to Milan, take the train! Don't bother with the hassle of renting a car and driving in unfamiliar territory. Relax instead! Probably cheaper, too.

This will be a very full trip, but I don't think it's "crazy." Everyone will have different takes on how much or how little time to spend at each place, but I think your breakdown is fair. You will have to be very choosy about your Venice and Rome time (do lots of research, figure out your priorities, and accept that you'll enjoy what you saw and miss everything else, catching it on another trip).

We flew in and out of Milan a few years ago and took the train from the airport to Venice. It's a fairly quick ride to Venice and after checking into the hotel and taking a look around you have pretty much avoided crashing too early. I'd do it again. We preferred Sienna to Florence and wished we had traded a day in Florence for another day Sienna or some other small town in Tuscany. On the day before we flew out of Milan, we made a half day visit to Stresa. If you are that close to the lakes you should not miss seeing them.

Congrats on your marriage and new jobs!

Italy is a fantastic place to have your honeymoon (my husband and I went to many of the same cities for ours). You've made a great choice.

Here would be my recommendation for some minor adjustments:

I'd allow maybe 1 more day in Venice and at least 1 additional day in Florence. August is hot and crowded so it will take you longer than you'd think to see the sights, and if you allow an additional day you can maximize your morning and evening sightseeing (when its cooler and crowds are lower).

Overall your plan is well organized and you've picked great locations to see! Enjoy!

Congratulations!

• I would stay in Florence for at least 3 nights.

• Keep in mind that spending 1 night in any particular place is equivalent to only a few hours
  of sightseeing. Thus 2 nights = 1 full day; 3 nights = 2 full days and so on...

• Don't underestimate how much time it takes each time you relocate from one city to the next.

• sometimes up to half of that travel day will be lost (checking-
  out, getting to train station, waiting for train/ bus, transit time, getting to new hotel,
  checking -in, unpacking, getting situated to new place, etc,
  etc...)

Have a wonderful honeymoon trip!

Wow! These are immensely helpful tips! We are really very much flexible and want to strike the right balance between seeing as much as possible and enjoying ourselves without running ragged from place to place. I do think the 1 extra day in Venice is a great idea (had been on the fence about it because that meant taking a day away from other places...) but a) I think Venice is going to be a great romantic place to see and experience and b) I think we'd really appreciate that extra day from a travel perspective.

Richard - any helpful tips on how you traveled from Florence area to Milan and the lakes? I'd love to visit Stressa or Como also!

Roma Termini to Stresa is about 3 hours with one train change, very easy to do and much quicker than driving, dropping off the car, etc.

Good tip about one more day in Venice, and about sightseeing taking longer. Plan on double the hydration/coffee/gelato breaks as you think you'll need. Stopping off inside a nice, cool church will be helpful, too. (Shoulders and knees covered.)

Stressa is a very short train ride from Milan. I think less than an hour. Our trip stuck with the north part of Italy. It was the same duration as yours. We went Milan, Venice, Florence, Sienna, Lucca, Milan with day trips to Stressa and San Gimingano. I agree with the others, don't short Venice. It's romantic even for a 65 year old.

This is all great information! Since I've got you all invested now... any suggestions on places to stay in Venice/Rome/Florence (or other areas in the tuscan region?)

"any suggestions on places to stay in Venice/Rome/Florence (or other areas in the tuscan region?)"

You can start with the Rick Steves Italy book. If you want further suggestions, you need to post a budget, in euros ("moderate price" means different things to different people), and any other needs/wants (elevator, canal view, etc).

Just thought I'd follow up since plans are starting to firm up and give you all an update. Here is our current itinerary:

Aug. 7 - Land in Milan and hop on a train to Venice. (Night 1 in Venice)
Aug. 8 - Spend the day in Venice, sightseeing, fighting jetlag. (Night 2 in Venice)
Aug. 9 - Spend half day in Venice and then get on train to Rome, have dinner in Rome. (Night 3 in Rome).
Aug. 10-12 - Three full days in Rome. We've book a tour of the Vatican and Colosseum so far. (Nights 4, 5, 6 in Rome)
Aug. 13 - wake up early and head to Florence, via train most likely. (Night 7 in Florence)
Aug. 14-15 - Florence, with a day trip to Pisa/Siena (Nights 8, 9 in Florence)
Aug. 16 - Leave Florence, rent a car and drive North. Stop in Parma/Bologna/Modena (havent decided yet) and maybe spend the night (Night 10 somewhere in Tuscany).
Aug. 17 - Arrive in Como area and spend the entire day and night (Night 11 in Como region, not sure where exactly yet).
Aug. 18 - head to Milan (with the rental car). Spend the day in Milan, possibly see the Last Supper, and just do general sightseeing/shopping. We have an early flight out on Aug. 19 so we booked a Hotel right near Malpensa Airport. We'll drive there after spending the day in the City and drop the car off at the Avis at Malpensa. (Night 12 in Milan/Malpensa airport).
Aug. 19 - Head back to reality/NYC.

So, I'm currently just figuring out the drive from Florence to Como area. Any tips on this? Any suggestions on places to visit along the way, if even for a quick bite to eat or a quick tour (like balsamic vinegar making in Modena, or Proscuitto tasting in Parma, etc.)

THANKS!!

Rather than juggle arrival with a train to Venice I would get a local train to Lake Como and 'acclimatize' to Italy.
Then you can book your onward trains with confidence because you will be on the ground.
Como (2)
Venice (2)
Rome (4)
Florence (3)
Milan (1)