Dear Italy experts:

I have been tasked with organizing a multigeneration trip for next summer. 13-14 people to the Lake Como area (from O'Hare, DC and New York) for up to five days and then each smaller group goes off on their own. We all need to make a one day trip to Chiavenna.

Have been to Rome, Florence, Venice before but know NOTHING about this area. Frankly, it looks rather boring and I have no idea what town(s) to stay in. Group wants to stay in a Villa but they look even more boring than the town and that means a car for 14 people!

How can I make this easy and fun?

First off, good luck with "fun and easy" for 14 people. You ain't gonna please everyone. Just admit that right now and save the stress of trying.
I'm in Varenna right now with 5 others. In a beautiful lakefront house in the center of the village. It's the yellow one next to the red one featured in every picture of Lake Como in every travel mag or brochure you're looking at. It's called Elizabeth House. Look it up and see what it offers. It's only 3 bedrooms and 2 bathrooms, so it won't work for you, just give you an idea of what a renovated village house can offer.
Varenna is a tiny village. Good restaurants and three most central location on the Lake. It's charming and also kind of sleepy.
But maybe what you consider boring, we're finding relaxing. Maybe being in one of the most beautiful places on earth doesn't jazz you.
What are you looking for? Casinos and discos? Shopping in the designer shops found in every major city? Hobnobbing with people you can name-drop when you get home?
Try Bellagio. Maybe you'll find what you need there. You'll certainly have a tab you can brag about being able to afford.
Seriously, give us an idea of your travel style and you can get some decedent leads.
But a group of 14? I'd seriously look at matching personalities and breaking it up into smaller lodging units.

I second Varenna as the top choice on Lake Como. It's worth it to splurge for a waterfront view, because it is truly stunning. Another great hotel there is Hotel du Lac. Bellagio is a bit hectic and crowded in the summer. Around the lake there are fireworks, music, etc.

If easy is the goal, pay someone to plan your itinerary! That's a lot of people and you won't please them all, all of the time.

If you want to force people to spend time together, you might want to stay on an island. I visited one in Lake Como that was like a small village with some restaurants and modest shops but not much else. Of course everything was walkable.

Thank you so much for the fast replies! I had read about Varenna and it seems to fit the bill. Can you tell me more about it? And the Elizabeth House looks very nice. We don't mind splitting up-do you think we could get another house nearby? That might be better for everyone too Group is in good shape/can walk, hike, swim and likes independent travel, art, culture, food. Half have been to Italy before/half not. Oldest is 70, youngest is 10.

Don't want to pay anyone to plan this. I can do it, just need inspiration.
And Bellagio sounds too expensive.

I assume you mean three generations, meaning elderly and less mobile, down to teens or pre-teens. Lake Como is great if you choose one of the towns with a ferry, e.g., Varenna. The older ones can visit the different towns and take journeys by ferry to different areas of the lake, and also just enjoy the view from the balcony or waterside. It tends to be cooler than other areas of Italy, and it has some great food.

For the younger ones, it's on a lake. Varenna has a small beach. They can kayak, motor boat, sail, fish, waterski, wakeboard, go to the large beach at Colico, kitesurf, snorkel, canoe, paraglide, stand up paddle, windsurf, hike up the great trail from Varenna up to the old castle di Vezio, hike in the wooded paths with a guide, take a tram to the top of the mountains, go canyoning, horseback riding, visit archeological sites, dozens of museums, attend the music festival that runs from April through September, catch a fireworks on the lake display.

There's no way to do more than scratch the surface. And you won't suffer from the oppressive heat of Italy in the summer.

There are at least 5 vacation rentals I've seen within steps of Elizabeth House. Not all are lakefront, but they all seem to have lake views from their terraces. The "streets" leading up from the Lake here are really steps, so the houses get higher as they ascend from the lakefront thus the views don't get obscured.
The two kids I'm with - ages 10 and 12 - love the lake. They're in it every day. There's an abandoned castle above the town that you can explore on your own. The boys found old armour and weapons laying about and played knights. I climbed to the top of the tower and had a phenomenal view from the battlements. A falconer gives demonstrations most days (check the website for Castello di Vezio for times). A really nice but steep path leads back down to town. (We took a taxi up...too hot for the steep ascent today).
Varenna is the central ferry port to visit the towns in the mid-Lake area - Bellagio, Tremezzina (lovely Villa Carlotta), Menaggio, and Lenno/Villa Balbianello.
You can catch the train from Milano Centrale to Varenna, which I'd recommend because parking is scarce here. Private excursions, both auto and boat, are available in town.
The restaurants in this village are surprisingly good. Tonight my wife and I ate at La Vista, overseen by a world class chef, who imo could work anywhere in the world, but I understand why he'd choose Varenna. Dinner for two, three courses with wine, came to 115�. We were there for two and a half hours. Delightful.
Let me just say Varenna is a place, if you know what I mean. And it's contained enough to make your planning achievable. (Obviously, I love it. This is my third visit.)
Best of luck.

Oh, thank you so much. I AM getting inspired and will have more questions soon after I do a bit more research. Enjoy the rest of your time there!

Very close to Elizabeth House is Cavatappi (corkscrew). Have you tried it? It's a tough reservation, people reserve it a year in advance because there are only about 8 tables. I've been lucky to get reservations there by stopping by the night before.

Not this trip, but last time we were here - in late September - we dined there. It was superb. With La Vista, the place that stood out on that trip.
I've found the quality of restaurants overall in Varenna has improved noticeably since our first visit in 2010. (And it was quite good then.) For example, in 2012, the restaurant attached to the Royal Victoria Hotel on the square was a simple cutlery-and-napkin-in-a-paper-bag, open-air, plastic chair kind of place with decent casual food. Two nights ago, we dined in their enclosed, air conditioned glass atrium and shared an exceptional asparagus risotto. Now it's a silverware by the course, cloth napkins, upscale patio (Still, the kids had pizza. I tasted the crust and it was definitely not frozen, delivered by truck).
This year, I've noticed Varenna has adopted the motto "The Lake Como you expect." I think they're trying to present the town as having a certain elegance without the rather notorious pretention that has made Bellagio something of a caricature. So eating and sleeping here are very pleasant, but there's no nightlife to speak of (beyond the passarella) and the shops are predominated by small local craftsman and their wares instead of designer labels.
Don't get me wrong. Bellagio is a very lovely picturesque place, but it has embraced a monied celebrity lifestyle that has come to define Lake Como to the general public. Ironically, I think the public perception of Bellagio has helped little Varenna maintain its character (it could become like sad Vernazza in CT if overcrowded) by dissuading many travelers from visiting Lake Como for fear of busting their budget.

We have spent time in the area above Argegno & had a fantastic time. Again the ferries are there to get around the lake & villages such as Pigra get you away from the crowds. Unfortunately for you I don't think Pigra has any Villas to take 13-14 but it makes for a good ride up on a funicular, a wander around the old buildings & then a great meal at the pub.

I wouldn't worry about finding a place that sleeps 13-14 if you choose to stay in Varenna. There are places next door to one another, or down the street. People can still meet on the patio for breakfast, by the lake for picnics, etc. Three generations aren't going to go to sleep or awaken at the same time anyway. You'd need something like Hotel Grand Serbilloni in Bellagio to sleep that many.

Perche and RickG,
Do you think it would be possible for us to hire a driver(s) from Varenna to take us to Chiavenna for the day and back? How would I go about finding that for all of us?