Milan to Lago di Como or Lago di Garda after flight?

Nicole,
You may want to consider another option.

Take the train to Verona after your flight, then after a good nights sleep and a delicious breakfast, pick up your rental car and drive to Ortisei.

I’ve not been to Ortisei (yet) but have taken the train to Verona on day of arrival (after a transatlantic flight from the West Coast)

Don’t underestimate how exhausted you may feel and how jet lag will affect you.

I’ve read that driving when sleep deprived is like driving under the influence.

I’d urge you to reconsider your plan and avoid driving on day of arrival.

Wishing you a wonderful trip!

Edited to add:
Keep in mind that the freccia (high- speed) train will get you to Verona much faster than driving.

Thoroughly agree with Priscilla about not driving while jet lagged. You could even take the train all the way to Bolzano, spend a night or two, see the Archaeology Museum, then rent your car and go to Ortisei.

Good for you for thinking about jet lag. You're getting some good advice here. I second the idea of a night in Verona, then get the car. Bonus: Verona is delightful.

I didn't think about Verona. Thanks for that suggestion! Originally we were planning to take the train all the way to Bolzano, but I'm nervous it'll just be too much for our 5 year old (forgot to mention she'll be with us.. oops!!)

I'll take a look at options in Verona. What's there to do/ see there??

Also, I'm assuming it's better to stay near the train station??

The Verona train station is actually a bit far from the center of town, so I don't think staying near it would be too appealing. You could take a cab to your lodgings, though - I walked, but wouldn't with a 5-year-old. It is indeed a lovely city. It's fun just to walk around, especially where there are views of the Adige River. The Piazza Bra has a Roman amphitheater that's used for opera performances in the summer. I enjoyed visiting a couple of churches, San Zeno and Sant' Anastasia, and the Giardino Giusti.

There is a lot to see in Verona. If you land at Malpensa at noon, you won’t be in Verona before 3pm, but that should give you enough time for a quick city visit of the Arena, Piazza delle Erbe, Torre dei Lamberti, the Scaligero bridge. They are all in the same area.
Rental car offices are not far from the station. Europcar is on Piazza Simoni, just 10 min walk from the Arena. Hertz is about 20 min walk from the Arena.
Based on my experience doing these things (renting a car the day after arrival), I like to stay in a hotel as close as possible (walking distance) to the rental office where I’m picking up the car so I can walk to it after I check out.
If you depart from Verona you are only 2 hours from Ortisei. I would take advantage and take a detour drive along lake Garda

nicole,

I also agree the the previous advice to take a train to Verona and rent a car there after you've had a good night's sleep. A couple of additional points to mention.....

• When is this trip taking place? If you'll be staying in Verona during Opera season, it would be a really good idea to get a hotel booking as soon as possible.
• I'd suggest staying close to Piazza Bra, as you'll be close to restaurants and will be able to to do a bit of exploring. You could consider THIS Hotel. IMO, I wouldn't bother visiting the fictitious "Romeo & Juliet" balcony, but your choice.
• As mentioned earlier, the station in Verona is a short distance from the city. Using a Taxi is the easiest option. Also use a Taxi to get to the car rental location.
• Does your five-year-old require a car seat? If you're not bringing one, you may have to enquire about that in advance.
• A GPS or at least a good map is advisable. If you're planning to use Google Maps on a smartphone, be sure that you have a data plan that will cover that.
• Once you've picked up the car, don't drive back into Verona as there may be a ZTL (limited traffic) zone, and you'll incur hefty fines. ZTL's exist in many towns in Italy so you'll need to be vigilant.
• You may be aware of this, but note that each driver listed on the rental form will require the compulsory International Driver's Permit for driving in Italy. These are used in conjunction with your home D.L. and are valid for one year. You can easily obtain an IDP at any AAA / CAA office for a small fee.

Alright, you guys convinced me! We've changed our plan and will train it to Verona from Milan.

Now my question is, how much time do I need to account for to get from Malpensa to Milano Centrale and navigate through the train station? 3 hours? So if we land at 12:30 and will have to clear customs and pick up a checked bag, should I reserve a train ticket any time after 3? 2 maybe?

Don’t reserve anything.
Buy the tickets on the spot at the Malpensa Station when you get there. Seats don’t sell out.

It will cost you a bit more, since discounts will no longer be available, but that way you don’t risk losing anything in case the plane is late. Discounted tickets are not refundable if you miss the train you book.
Besides, the most you can save with a discounted ticket (Super Economy fare) on that specific segment is only about €7 per ticket, so not really a fortune.

nicole,

To help a bit more with your planning, the Malpensa Express from MXP to Milano Centrale takes about 52 minutes. A few important points to note.....

• the M.E. is a Regionale train so DON'T forget to validate (time & date stamp) your tickets prior to boarding the train or you'll risk hefty fines which will be collected on the spot.
• the M.E. has two destinations, Milano Centrale and Milano Cadorna. Be sure that you board the correct train!
• as Roberto mentioned, do NOT buy advance tickets from Milano Centrale to Verona. The train will likely be a Freccia which has compulsory seat reservations, and those tickets are specific to train, date and departure time. If you miss the train, your advance tickets will be worthless and you'll have to buy more. If you board an express train without having a valid reservation for that specific train, again hefty fines.