If relaxing is a priority I’d cut at least one place and slow things down. I’d give more time to Paris and London, and if you can fly home from somewhere else I’d skip Frankfurt (but I know you may not have tons of options using miles). Geneva wouldn’t be big on my list either.

The main places I want to go in Europe is London, Paris, and Italy. I like the idea of taking a train to see the countryside. So, the stop in Switzerland was a connection place. And my airline (American) main hubs are Paris, London, and Frankfurt. But, thank for recommending longer in Paris and London. Is it too long in Italy? I was thinking since it is winter it would be slightly warmer down there…

Big cities like London and Paris really “need” 3 full days. 4 is better if you want to take a day trip (like getting out of Paris to wine country for your anniversary). With the travel time involved, 2 days in Paris is hardly worth it.

6 days in Florence and Venice is about right. I would cut a day from Venice to spend in a smaller city/village. I don’t think you can manage to add Rome without skipping either Paris or London, but if you’re interested in Italy, it’s a shame to miss Rome.

I would cut Switzerland from your itinerary and fly (see our “cheap flights” forum for info on low fare airlines) or take an overnight train from Paris to Italy.

I’m not sure how much you’ve already looked into flights or if it’s the same with American, but I regularly find open award seats to United’s non-hub destinations when some of the hubs are booked solid. During the summer of 2009 I used miles with United and ended up calling and booking with an agent because they have access to seats, especially on their partner airlines, that just weren’t available when I tried to book online United charged a fee for this (I think $75), but my wife and I were able to get a decent itinerary that we couldn’t find online. Good luck.

Oldlady and Augustin offer good advice. I definitely would cut Switzerland, you simply do not have the time.
Keep in mind that Italy will not be all that warm in January, but I’ve always thought that Tuscany with snow would have a charm all its own. I agree with Oldlady about taking a day off Venice and seeing a small village instead, and I also agree that it’s a shame to miss Rome, but you can only do so much.

So what small village could you recommend? So far, I’ve extended London (5-days), Paris (3), Florence (3 or 2), Venice (2), and flying into Frankfurt (2)…Am I getting closer?

Smaller towns to think about in Italy:
Lucca, Siena, San Gimignano, Pienza, Cortona.

I caught this thread a little too late, but in case you haven’t bought your air tickets yet, I really wouldn’t waste my airmiles for Europe in January based on the things that you want to see and do. I hope you’re aware that Europe is temperate. At best, it’ll be as cold as Alabama or North Carolina (southern Europe). At worst, it’ll be as cold as the Minnesota or Quebec (northeastern Europe).

I would advise you save your airmiles for spring/summer/fall, or maybe consider Australia, Thailand, Vietnam, Brazil, New Zealand, Chile, or Argentina.