Driving around the Dolomites

A car would be very inconvenient in Milan. Can you drop it outside the city and use public transportation for your time there? Other than that, it would seem fine as long as you will be in Italy already and recovered from any jetlag.

Yes
I am planning on dropping the car off at outskirts of Milano

This is a partial reply to your post. I am not a single traveler, so can't help with that part. I do have some comments on our experience driving in the Dolomites. As part of a larger trip, my wife and I rented a car last summer just for the Dolomites part. We drove from Verona to the Bolzano/Lajen area. We stayed about 4 days and did a fair amount of local driving.

The highways and major roads are great. The smaller local roads can vary from easy to quite narrow and steep. With the two of us there was no trouble. Everyone's experience is different, but I wouldn't have wanted to drive some of them solo at night. Also you should take into account if you want a manual transmission or automatic car.

We had a great experience seeing these very real mountains and hope you do as well.

Thank you; i was planning on no night driving.
You bring up an interesting point about verona. It could be a helpful alternative for car return.

Thanks

Yes— I think it’s totally safe and doable for you to visit the Dolomites solo. Can’t think of why it wouldn’t be. I’m starting in Milan and also renting a car to get to the Dolomites before continuing to Venice. You can rent through AutoEurope in Venice or Padua ( 30 minutes by train) and return it to Verona or Bolzano after visiting Selva di Val Gardena.
Gardena is about a 1:40 drive from Cortina d’ Ampezzo and a 55-minute drive from Bolzano; Padua to Bolzano is about 95 minutes by train; Milan another 75 minutes by train.
www.TheTrainline.com
www.AutoEurope.com

Driving in the Dolomites as a solo woman is totally doable and generally safe. The roads are well maintained and italian drivers in the north are way more predictable than in the south lol.

Your itinerary looks pretty solid! Just a few things to keep in mind:
The mountain roads have lots of switchbacks/hairpin turns. Take em slow, especially if you're not used to mountain driving
Parking in Cortina can be tricky in peak seasons. Most hotels have spots but double check with yours
For the Lake Braies drive, try to go early! The parking lots fill up crazy fast and you might have to park pretty far if you arrive after 9am
The drive to Milan will take around 5-6 hrs depending on traffic. Plan for breaks since mountain driving can be tiring

For the hiking day - definitely recommend going with a guide first time. They know all the best spots and weather patterns, plus its nice having someone who knows the area when hiking solo.

Quick tip - if youre not super confident with Italian roads/signs, might wanna check out Tripiamo before your trip. They've got really helpful guides for driving in Italy that cover everything from road rules to common situations youll run into in the mountains.