10 Days in Lake Como/Dolomites
 

Super excited to check out this area! Rough draft of the itinerary before I start planning specifics.

Day 1: Land in Milan, train to Lake Como
Day 2: Lake Como
Day 3: Lake Como
Day 4: Lake Como
Day 5: Rent car, drive to Dolomites
Day 6: Dolomites
Day 7: Dolomites
Day 8: Dolomites
Day 9: Drive to Milan or Venice, spend day there
Day 10: Flight home

This is our 15th anniversary trip, just my wife and I (early 40's). We like both being active and getting out for some hikes, and also relaxation.

Some questions

1) Is this enough time in each spot? Too much? It's possible we could work an extra day into the trip. In that case which place should we add it to, or should we add a 3rd destination?

2) Our current dates are Sep 4-13. With those dates in mind in the perspective of weather and crowds is it better to do Como first and then Dolomites, or vice versa?

3) We could push our dates back a week to Sep 11-20, would that be better to have lower crowds or would we be more likely to run into issues with the weather (my wife likes warm if possible) and gondolas closing in the Dolomites?

4) Should we stay in one spot in the Dolomites or move around several times?

Where would you base at Lake Como? And in the Dolomites? What specifically do you plan to see/do in both areas? Whether you have enough time in either/both places depends on the answers to these questions.

FYI, car rental offices at Lake Como are in Como and Lecco, but neither is where I'd want to base. You don't "need" a car to explore Lake Como. Depending on your plans, the car will likely sit parked, accumulating overnight parking fees in addition to the daily rental cost.

FYI#2, the drive from wherever on Lake Como to wherever in the Dolomites is long. You could drive over the famous Stelvio Pass, but it would be a day spent sitting in a car.

FYI#3, if this is a one-way car rental, you should investigate the amount of the surcharge that will be added to the rental. Alternatively, you could train from Lake Como to Bolzano and rent/return the car there.

Weather is unpredictable, esp. in the mountains, but September should be generally good in both places. If you want to do the Dolomites first, fly into Venice or Verona. Fly home from Milan to eliminate backtracking. Or do the reverse, into Milan and out of Venice.

If you haven't looked at lodging in both places, you should get on that asap. September is a popular month. In the Dolomites, since it's a relatively short stay, I'd pick one base.

Impossible to answer your questions as long as you don't tell us where you really want ot go and which places you plan to visit.
A drive from Lecco (Lake Como) to Predazzo (Dolomites) takes 4 hrs whereas a drive from Garzeno (Lake Como) to Comelilco Superiore (Dolomites) takes 8 hrs.
Gondolas in the Dolomites: some of them run all the year round, some close in late September and others at the first weekend of September. All depends on the places you chose.

Closest airports:
Lake Como: Linate, Malpensa and Bergamo
South Western Dolomites: Verona and Bergamo
South Eastern Dolomites: Venice
Northern Dolomites:Innsbruck and Munich

Weather: as above (always unpredictable in the Alps)

Thanks for the reply!

In Lake Como we'll be staying in Varenna.

My priorities in the Dolomites are Seceda and the Tre Cime/Cadini di Misurina area. Relatively open after that, probably stop by Lago Di Braies as well.

We're also planning an extended trip to the Dolomites, but in late Sept/Oct. I've compiled a list of open/closed cable cars for our trip; you're there early enough that closures shouldn't be an issue.

San Candido is the closest town to Tre Cime National Park and Lago di Braies. We plan to visit Misurina from a San Candido base as well.

Seceda is easy to reach from Ortisei, S. Cristina or Selva in Val Gardena. Of these three, Ortisei is the most bustling.

San Candido to Ortisei will take about 1:40 by car.

FWIW, we stayed in S. Cristina and San Candido in December, during our first visit to the area. We loved San Candido, and have booked five nights there again this year.

Whatever you choose, you should probably book pretty soon. I suspect you'll be wishing you had more time in the area; loads to see and do, hence our return visit.

Definitely not 'too much time'. If you were to add a day, personally, I'd add it to the Dolomites, but just extend your stay in the same place.

For this itinerary, car is faster than public transport.
Seceda gondolas: open until end October
Seceda chairlift: open until med Sepember
Gondolas Sesto - 3Cime del Lavaredo: open until end October
Bus Toblach - Auronzo Hut: runs until mid October
Bus Tai di Cadore - Auronzo hut runs until mid September