Where to start arrival Milan

First of all, you'll have to take the train to Milan, and from there, I'd suggest you look at either Venice(my first choice) or Florence. To either there is a fast train, and, from either, you can take fast trains south. I normally allow myself 3 hours from estimated landing at MXP for PP control, baggage, and the 45 to 60 minute ride on the Malpensa Express to Centrale.

If I were you, I would stay one night in Milan. The Duomo and the Galleria were amazing. I didn't expect to like Milan and only booked one night there before heading up to Varenna to start our tour. After checking into our hotel, we took the Metro to the Duomo. The Metro is really easy to use. I was amazed how beautiful the Duomo was. It was a lot of fun to walk around on the roof of the Duomo and to walk thru the Galleria. I wished we would have booked another night. Don't sell Milan short. You can do a lot in just one day while over coming your jet lag. Also, if you haven't been to Venice, I would head there for at least two days. It is a great city and a great place to spend your 25th wedding anniversary.

You can go to wherever you think you want to start your trip: Venezia (Venice), Firenze (Florence), or even Roma. If you want to go to Lago di Como, that is super, too. Just take the train from Malpensa airport to Milano Centrale and connect to wherever you wish to spend your first night.

Personally I agree with JerryG on Venezia being a great intro to Italy and a terrific first stop.

You have 14 nights. With that amount of time, I recommend no more than 4 different stops, Roma and north. A classic first trip is Venezia, Firenze and Roma. You could add in a Tuscan hilltown, Assisi, Lago di Como, or Orvieto to give you a small town taste.

Your open end question is difficult to respond as the options are infinite. Also you don't specify whether you intend to travel by car or train or a combination of both.

If you are not interested in Milan and would like a nice place to relax for a few days on a lake, I would recommend to go first to Lake Maggiore (e.g. Stresa), which is next to the Milan Malpensa airport. Lake Maggiore is not only very close to the airport, but in my opinion it is just as beautiful as Lake Como (which isn't close) and with many more things to offer. I recommend at least 3 nights in Stresa to fully enjoy what the lake has to offer.

To go to Stresa you can use the following options:
1. rental car (45 min drive)
2. Shuttle bus (55 min drive) - (http://www.safduemila.com/alibus-2015-malpensa.lagomaggiore.html)
3. Train. Two options:
a. From Malpensa Aeroporto station to Stresa with one change in Saronno (1hr 25min)
b. Taxi from Malpensa airport to Gallarate station (10-15 min taxi ride), then train directly from Gallarate to Stresa (35 min).

If you prefer to go directly to Venice, as suggested above, you can do so by train. First take the Milano Malpensa Express train from the airport (Milano Aeroporto station) to Milano Centrale (52 min train ride), then at Milano Centrale take a high speed train to Venice (Venezia Santa Lucia station) (2h 35min train ride).

As I said there are tons of other options depending on what you want to see.

Train schedule is below. Use Italian names for cities (i.e. Venezia not Venice, Firenze not Florence)
www.trenitalia.com

For the train from Milano to Venezia, you want Venezia Santa Lucia. Firenze will be Firenze Santa Maria Novella.

I also recommend a night's stay in Milano. If you book tickets Milano to Venezia early enough (120 days out), you can usually get a 9euro supereconomy ticket - easy if you spend the night and can plan your train departure time with certainty. Just don't miss the train, no exchanges or refunds on the supereconomy fare. So you could leave Milano the next (late) afternoon and be in Venezia for dinner.

Very sorry for not being more clear. We are intending to rely on train transportation for the entirety of the trip. I am happy to hear support for going to Venice. We heard from people in Seattle that it has become overly commercialized and crowded so skip it. If not true I'd be open to a few days there starting day one then take the train South for remainder of trip.

From your 14 nights, take 4 nights for Rome, 3 for Venice and 3 for Florence.

That leaves you 4 nights remaining ...
Choose two of the following three - Lake Como / Tuscan countryside / Cinque Terre - each for a 2 night stay.
or
Spend all 4 nights on the Amalfi Coast

you are not flying into Milan, you will be in Malpensa which is about 25 miles from Milan.

Everyone has been so helpful! Thank you all. Now wejust need to sit down and compile your ideas into a solid plan. I really appreciate the nights per City suggestions otherwise we'd spread ourselves to thin.
Regan.

We heard from people in Seattle that it has become overly commercialized and crowded so skip it.

Yogi still said it best, "Nobody goes there anymore, its too crowded!"

This could be said of almost anywhere, Paris, London, New York, or even Seattle. Venice certainly is not what it was 25 years ago, or 50 years ago, or 100 years ago. Nothing is. The addition of about a billion people to the middle class in the last 25 years may have something to do with it. Guess what, they want to do the same things you do, and seeing Venice is on the bucket list. Add the introduction of 1000+ cabin cruise ships with 3 or 4 parked at the Stazione Maritima and it can get busy.

Venice is still amazing and there is certainly no place like it on earth. Stay there after the day trippers are gone and enjoy. People who say the sort of things in the quote are really saying "We were there before all those tourists ruined it." But what were they?

Venice is great no matter how many tourists are there. A city unlike any other. You mingle with people from all over the earth. Everyone is cordial and polite. I loved the city.

Personally I like to not do big cities the first few days I arrive. Since you mention 25th Anniversary & jet lag, yes Lake Como is a perfect place to start your trip. Varenna is nice, and an easy 1 hr train from Milan. I started a trip there with 3 days on the lake and loved it.

Bologna is short train trip from Milan and I really like the city. Not as much a big Museum city like Florence, but nowhere near the crowds either. Great food, wonderful sites, and usually some great summer activities in Pizza Maggiore. There is an added advantage of so many Porticoes so you can stay out of the sun while you walk around the city.

Couple of added points when going Italy in July-it will be HOT! This past July we were there the last week of July and it was hotter than normal; we did a lot of our touring early and late and not during the mid-day, so pack accordingly with light and easy to wash and dry clothes. For the first time in Italy, I and many other guys were happily wearing shorts and spouse was happy in her skirts. Also, you can Google "cruises docking in Venice," and find out when, how many, and how crowded (500,1000, 2000) it will be in the square and St. Marks so you can plan your visits. Finally, go out of your way to "get lost" if you go to Venice-that's were the intimate trattorias are.

We did the RS Venice-Florence-Rome trip last June. It was very hot and crowded...but a great vacay!

We flew into Milan and immediately took the fast train to Venice...but we were flying back out of Milan 14 days later....so we had time at the tail end of the trip and we spent a day in Lake Como...Varenna, Bellagio, etc. Absolutely beautiful.

There's not a "ton" to do, but relaxing and taking the boat around to the different towns was great. Eat good food, drink great wine, watch fabulous people. For us, it was great to "relax" at the end of the trip. No museums, no art galleries, no churches. After 10 straight days of seeing the Madonna and Jesus in various forms...it was nice to decompress.

Even in June, Como wasn't too bad as far as tourists.

It was a nice way to remember the end of our trip.