Getting to the Dolomites

We have been 3 times, in late August and late September and had variable weather each time. But September should be notably quieter as the Italian kids go back to school at the end of August. You will see most hotels offer better prices at that time.

That said, our next visit will be in July because we are meeting others and that is when they can go.

As for you car rental, it is best to rent it in Italy to avoid the drop fee incurred when you rent in one country and drop in another. So you could rent in Venice and drop in Florence without incurring the drop fee. Or do as we did, fly into Munich, take the train to Bolzano, and pick up the car there.

I agree with Lola. The region north of Venice--when you hit the mountains--is just breathtaking. And it gets even more beautiful when you get up around Lienz, Austria which is on the Italian border east of Cortina. The Dolomites and the Alps are very high in elevation.

Thank you very much for your quick replies. Sounds like maybe Venice is the way to do it. We will be newly retired and are avid hikers but not mountain climbers. I have read that the snow has pretty much melted out in the areas where you would hike, by July, and that the wildflowers can be breathtaking. Is that your experience? We would love to see the flowers but wouldn't want to be hiking in the snow.

We loved walking in the mountain meadows way up high! No snow in June when we were there. Beautiful place, enjoy!

Side note, check out Gillian Price's Hiking Guides for the Dolomites. We found the short hike guide to be very useful. The area is also filled with chair lifts and gondolas from the ski season that are available during warmer weather.

We have been there in July and Sept. We spent an entire month there in July 2016 and it is indeed peak wildflower season. Not as crowded nor expensive as August, warmer then September but (usually) not uncomfortable as you are at a high elevation.

The book "Walking in Italy's Val Gardena" will be your friend. We found it invaluable for learning the ropes about the area not to mention the detailed guides to 23 different walks to take (you'll need more time!).

Have you decided where, exactly, you want to stay? It is a big area. In some valleys, you can park your car and not need it during your stay, which is convenient and relaxing.

We go to the Dolomites fairly regularly. The easiest place to fly into would be Milan...you can rent a car and go straight north and be in the mountains in just a couple of hours. July is better than August but don't expect there NOT to be crowds...no matter when you go it is a very popular place and there will be plenty of other people. I was just there in September a couple of years ago and there weren't too many people and the weather was still very good - that's a crap shoot though that time of year depending on if you go earlier in the month, or later.
Another option would be to rent the car in Venice...that way you can drive up to the Cortina d'Ampezzo end of the mountains, work your way from east to west, and then come out of the mountains headed south toward Milan and then down to Florence. That way you can also spend a couple of days in Venice to get over jet lag - talk about crowds though...ugh...Venice in July. If you go in September it isn't too bad...still plenty of people but NOTHING like summer.