First time in Italy and going for a month.

It looks like a pretty sane itinerary to me, though I know you're going to hear from the Florence lovers about having just two nights there. Do you really dislike art museums?

I'm not sure you're really going to get much value from the rental car in the Dolomites. From Milan you can get a Freccia train to Verona (on the same rail line as Venice) and change to a northbound train that will take you to Bolzano. There's bus service from Bolzano up to Ortisei, which many of us have used. As little time as you're going to have in that area, I'd think you could easily just use the buses. When you're ready to head to Venice, you'd take the bus back down to Bolzano, catch a train to Verona, then change to a Freccia train going to Venice.

I'm not sure you need a car and driver to travel from Atrani to Naples. You could return to Salerno and get a Freccia train to Naples. You wouldn't be dealing with the not-very-popular Circumvesuviana.

joel,

Your tentative Itinerary looks reasonably well organized. It's late and I'm not focusing well so just have a few initial comments.....

• As you're planning to drive in Italy, be sure you do some research on the potential caveats. For example, each driver will require the compulsory International Driver's Permit, which is used in conjunction with your home D.L.
• You'll have to be extremely careful to avoid the dreaded ZTL (limited traffic) zones which exist in many Italian towns. Each pass through one may result in a hefty fine, which you may not know about until after you return home. Florence is extensively covered with automated ZTL cameras, so not a good place to drive! There are also tolls, speed cameras, etc. I find that I can generally get to most places using well planned public transit. If you want to enjoy the wine in Tuscany, you might consider booking a tour with someone else doing the driving, as you'll be able to enjoy the wine without any driving worries.
• As this is your first trip to Europe, I'd suggest reading the Rick Steves book Europe Through The Back Door to begin with as it provides lots of great information on how to travel well.
• You might want to also pack along a current copy of the RS Italy guidebook, as that will be a big help to plan touring, hotels, etc.
• There are also some potentially expensive caveats with rail travel in Italy, so it's a good idea to familiarize yourself with that as well.

To answer your question about getting to Varenna, when you arrive at MXP you'll need to take the Malpensa Express to Miilano Centrale, and then connect with the Regionale train to Varenna. You can buy tickets at the airport rail station. Note that the station is called "Varenna-Esino".

Many people these days travel with smartphones, and with the Trentialia or other app's such as Trainline, tickets can be purchased online. Of course if you plan to book tickets "on-the-fly" and WiFi isn't available, you'll need to have a cellular data plan.

One other point to note about Trainline..... they're a reseller and may charge a small service fee. They can provide tickets for both major rail networks in Italy, Trenitalia and Italo Treno, as well as many other rail networks around Europe. Once users are registered on the site with payment information, I've found it very easy to book tickets.

Luis Silva is just promoting his business. Beware. Reported.