So if you had to choose a place in all of Italy to hang out for a few days in super-luxury, relatively car-free, and using a boat to access restaurants and islands nearby, where would you choose?

I would choose Positano in late September.

Positano is one of those rare places that you find that has just about everything with some gorgeous hotels (Le Sirenuse and Hotel Covo dei Saraceni) and some very cool restaurants that you either have to walk along the cliffs to or rent a private boat to access.  Positano has a constant flow of ferry traffic as it serves all the way through the end of September as a main jumping off point for tourists from Sorrento and a jumping on point for tourists to get to the island of Capri.  The beach is typical of this area – stony with plenty of stabilimenti. The water is clear although it is good to stay inside of the swimming lanes because of the boat traffic.

I had not been to Capri for more than 30 years so we rented a boat and sailed clear around the island.  We landed at the Marina Grande and went to the Marina Piccola for a swim.

Capri is good for a day; no more, and maybe a bit less.

It was good to go but it was crowded and the wait on the funicular was not worth it.  The cab drivers all seemed to be satiated for business.  To make it worse, the water was choppy so the famous Blue Grotto was not available.  One thing’s for sure, Capri is beautiful but no Greek island.

Positano is spectacular and has almost the enchantment of a Greek island.

The colorful houses as they sit along the horseshoe cliff face are like no other in the world.  The smell of lemons in the lemon groves pervade this place.  The fact that you can buy fresh mozzarella di bufala makes this one of the great wonderlands of Italian cuisine.  It’s expensive, it’s trendy, it’s glitzy, and it’s a bit of a hassle to get to, but honestly, for three or four days at least once in your life, you should give yourself up to Positano.  Tom Brady did while he was sitting out his four games for Deflategate.  My only regret was that I didn’t bump into Gisele while taking my morning cappuccino.  We were there at the same time!