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9 days; 1or 2 home bases for relaxing, sightseeing and nightlife in Italy

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We are a group of 7 adults who have about 8/9 days to relax near water in mid-September. We like small towns with good food and nightlife; medium-priced hotels within walking distance to the town, with views, food on premises and pool bars. (We live in Key West and are rather spoiled.) I am looking for suggested itineraries with no more than 2 home bases from which to explore near-by sights.. We will fly into Rome or Milan and I have allowed an additional 4/5 days for sightseeing in those cities, arriving and departing. To give you an idea of our interests: We would choose a long lunch with drinks in a plaza over a couple of hours in a museum; a driver/tour guide to take us on day trips from our base, but would rent a car if it's a wiser economic choice. So far, cinque de terre and Bellagio, Lake Como looks interesting as does Capri, Sorrento and the Amalfi Coast. Two years ago our group went to Athens, Mykonos and Santorini and loved it. Mykonos was our favorite because of our hotel staff and bartender (do you see a theme here?) at Vencia Boutique Hotel in Mykonos Town and our close proximity to town. One lesson: 3 nights in a location is not enough. An important PS: one of our group has trouble with lots of stairs (santorini!). Also, we have been to Florence, Umbria and Tuscany and Venice, but not enough time in Venice. Thanks in advance for your input.

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