14-17 days in the lake region and maybe visit neighboring Switzerland

How much time do you have and in what month(s)? Length of time for your trip is a factor in knowing where to send you or if there is time to go to the Dolomites and/or Switzerland. Time of year is important for activities. Do you like to hike? Ride mountain bikes? The mountains are great in winter and summer/fall, not so great in early spring or right before ski season.

I am so sorry - I just saw the "14-17" days. Now as to time of year....

Assuming June-September,

2 nights Milano

3-4 nights Como (Varenna?)

How about 4-5 nights in the Berner-Oberland, particularly the Lauterbrunnen Valley? About 3 hours by car and car ferry. Or you could go to Lugano in an hour by car ferry.

Ortisei, my favorite place in the Dolomites, is 4 hours from Varenna by car or 6 hours from Lauterbrunnen. If you go there, try to give it at least 4 nights.

You might play around with routes on www.Rome2Rio.com.

A car will indeed make this more fun. We (a couple with two teenaged daughters) did a terrific road trip a few years ago from Bern through Lugano, auto ferry across Lake Maggiore to Stresa and on into Italy. Instead of taking the Gotthard tunnel, we went up and over the Grimsel Pass. The scenery was breathtaking, and the road was in very good condition. Even though it was only two lanes, with occasional passing lanes, and very twisty, it was well maintained and we felt very safe. We were very happy we had gone over instead of under. The Gotthard tunnel often backs up in the summer, and sitting in fumes waiting to go through a dark tunnel did not sound appealing. We stayed overnight in Lugano in a resort-like hostel (spacious family room, pool, gardens, play areas etc.). We would have enjoyed staying there longer.

If you were to do this trip in reverse, from Lake Maggiore into Switzerland, you could stop anywhere in the Berner Oberland (the route goes right through it) and enjoy some hikes and sightseeing there. Happy to send you tips on that too, as our oldest daughter spent a year as an exchange student there. This family trip was at the end of her year, so she showed us all her favourite spots. Here's the route: Bern to Lugano

A.,

You won't need a car for this, but one possibility you could consider is a visit to Stresa on Lago Maggiore. It's easily accessible from Milan and you'll easily be able to take a day trip to Switzerland.

As I suggested in another thread, you might consider a trip to Locarno on the scenic Cento Valli Railway, returning to Stresa in the evening by boat. I can provide suggestions on sights in Locarno if you're interested.

Another possibility would be to add a day to Milan and take a day trip to Lugano, which is only a one hour train trip.

Thank you all so much for these great ideas. I'm now thinking
FLY into Milan, spend 2-3 nights there,
drive to Lake Maggiore, 2 nights there (Stresa),
drive up to Lugano in Switzerland (not sure if my family wants to drive another 3+ hours north, so I'm working on exploring Switzerland more) and then go to Lake Como for a few nights and ultimately drive back to Milan to fly back to Chicago.

Thoughts? Lodging tips?

And we are going in the beginning of June 2016, probably the week of June 6. We just want to be back in Chicago by june 22 or 23.
Thank you!

That looks like a terrific trip! You've given yourself time to explore a reasonably-sized area without spending the whole time in a car or on a train. Have fun! The really cool hostel we used in Lugano is here: Lugano Youth Hostel. We didn't stay in the Stresa area, so I can't offer lodging advice there. I would encourage you to take a short day trip to Lake Orta/Orta san Guilio as well. It's really beautiful.

I'd like to add my two cents and recommend Lake Garda. We have visited Lake Como and Lake Maggiore and loved both. But I think I loved Garda even more. We stayed in Sirmione in a great apartment that was very economical. The drive around the lake was fabulous with lots of villages to pop into. We have also stayed in Castelrotto/Kastleruth in the Dolomites and have a wonderful hotel recommendation there, as well. If you can fit this in, let me know, and I'm happy to offer you any tips.

Hi A.
A few years ago, my husband and I did a 17 day trip that included Gimmelwald in Switzerland (an RS recommendation) which was absolutely amazing. We did our entire trip by train but getting up to Gimmelwald with the cable cars etc was part of the amazing adventure itself. I would highly recommend! Our train from Florence went through Milan on the way so if you need help on trains etc, let me know!

Here's my post from when we got back...
https://community.ricksteves.com/travel-forum/trip-reports/rome-florence-gimmelwald-bacharach-bruges-and-amsterdam-in-17-days-the-trip-of-a-lifetime

I'm not always a big fan of circle trips, why not fly into Milan and out of, say, Zurich or Munich? You could stay longer in CH and also visit Bavaria. don't forget, to take a car into CH you'll need a vignette or a large fine will result. Or instead of driving take the Bernina Express from the Milan area into CH and then train all over CH.

Thanks again for tips...question for PHRED: what is the CH you are referring to?

Others, we have booked 4 nights in Milan week of June 6 as a compromise with the 23 year old...next stop will be the Lake Maggiore area. do you know if we stay in Verbania near Lake Maggiore if it will be convenient to take a ferry to the islands or must we take a ferry out of Stresa?
Thanks
April

If you are committed to flying in and out of Milan, and want lots of lakes ...

Arrive Milan. Hire car. To Lake Como - 3 nts
Drive to Lake Garda - 3 nts
Drop off hire car and fly Venice to Geneva. Train to Lausanne - 3 nts
Train to Interlaken/Lauternbrunnen - 3 nts
Train to Luzern - 3 nts
Train to Milan - 2 nts

or

Arrive Milan. Hire car. To Lake Como - 4 nts
Drive to Lake Garda - 4 nts
Drop off hire car and fly Venice to Zurich. Train to Luzern - 3 nts
Train to Interlaken/Lauternbrunnen - 4 nts
Train to Milan - 2 nts

CH = Switzerland (Confederation Helvetica). Easier than typing Switzerland over and over (and it explains the bumper stickers you'll see over there).

thanks and we are making progress. just booked a rental in Verbania. Now we want to hit Lugano and whatever else we should in CH ;) and then wrap up in Lake Como...anyone know anything regarding Gravedona in the Como area? I have a Slow Food Italy book that lists a place called La Villa there.
Grazie!