A good friend and colleague recently asked for "anniversary in Italy/France" pointers, and I was only too happy to oblige. In fact, I gushed: "I'd be psyched to give you guys some suggestions, and, well, I'd also be happy to come along if you feel the need for a pocket translator slash food/wine taster! What better way to celebrate an anniversary than a third wheel?!?!"
Two days after sending him the email, still no response, so I guess that's a resounding "No, thanks." Anyway, I figured the thoughts might help out some of you as well. The circumstances are a little particular (visit Italy via France and build in a stay on Cápri, but maybe you'll find something helpful. Here's the email...
As for Cápri (principle destinations are Anacápri, Marina Grande and Cápri town), I've never been. My instinct is that your timing would be perfect, early season (end of May through middle of June), so not yet packed. The island has a reputation for being overcrowded and overpriced, so an almost pre-season visit would be advantageous. But I'm getting ahead of myself. Let's start at the top and work our way down the map. I'll throw some ideas at you to help you scheme up the perfect trip and then you can get back to me for more dilated thoughts on anything that strikes you. Sound good?
First of all, transportation. You said, "Can't do room bookings until we have dates nailed down for flights." Right. You also mentioned finding some of your best deals from Montreal. It sounds from your email like you're thinking of round tripping it to Paris? Or maybe just flying into Paris? Best flight prices will be Paris, Rome and Milan, and if you're thinking of a split ticket, then in to Paris and out of Rome or Milan seems like the obvious way to go. And Milan should have excess capacity by then (post winter Olympics) which means cheaper rates if you wanted to stay there for your final night. It's a great city, often overlooked by tourists.