Lugano v. Como

Lugano is cleaner, people respect road signs and don't run over pedestrians while on a pedestrian crossing. They are also more boring people and they think they aren't Italian even though they speak Italian and eat Italian. The only Swiss thing in Lugano is the prices (higher).
Como is just as pretty so it's a difficult choice. However George Clooney didn't buy a villa in Lugano, he bought it on Lake Como, so if George Clooney chose Como there must be a good reason. I always trust the judgement of men who can catch gorgeous women more easily than I could possibly hope for.

I was just in Lugano a week ago for the first time. I wasn't impressed - it's a beautiful area but extremely expensive (like most of Switzerland) and not much for interesting shopping or sightseeing (beyond the overall outdoor scenery). Unless you want to buy a Swiss Army knife, watch or chocolate (all overpriced) - I would suggest Como based on what I've heard other people report.

I think Como is the way to go! We loved visiting there for the day and noticed there is so much to do. The Ferry gives you access to all the small towns around the lake like Bellagio and Menaggio. You really have a lot of choices and logistically it is super close to Milan and the Swiss alps. I would choose Como based on landscape, size and activities. AirB&B has tons of places to stay. Also look at Booking.com for local hotels that you can stay in towns you like.

Jordan,

Could you clarify whether you're planning to stay in the town of Como or one of the other towns along the lake? I tend to agree with the others that a stay on Lago di Como would probably be a better choice. While Lugano is nice and does have some beautiful scenery, it IS more expensive and somewhat more "upscale". I've heard that it's the second most important financial centre in Switzerland behind Zürich, so the price level probably isn't surprising. I'm sure the Casino there does a thriving business!

Thanks for the thoughts. It sounds like the opinion is unanimous toward Como. One of the options for towns we're looking at is Varenna. Since we'll only be there one night after a day of driving, we'd prefer to be somewhere beautiful and relaxing that doesn't have many must-see sights that we'll feel obligated to see while we're there.

Jordan,

Given your criteria for a "quiet" location, Varenna would be a great choice! If you're driving, I have no idea what the parking arrangements or costs will be. If you're travelling by train, it's an easy one-hour trip each way from Milano Centrale.

Jordan, Ken's question could be important for you: his question was, "Could you clarify whether you're planning to stay in the town of Como or one of the other towns along the lake?"
Big difference between the two.