Italy
Any bar on the piazzetta, the teeny town square, in central Capri is a memorable place to have a drink and enjoy the sometimes overwhelming spectacle that is Capri. Rich and poor, celebrities, fishermen and gigolos, whatever strikes your fancy, is on parade in La Piazzetta, the living room of the world. Al Piccola is a good one... well, all of them with outdoor seating are memorable. It is a very happy place and you do feel like you are a celebrity (undiscovered? in disguise?) to just sit there and watch the world go by. Try the bar at the top of the funicular. Delicious cheese sandwiches, good drinks and a view that will make you cry.
Surprisingly, and a very well-kept secret, Capri accommodations can be reasonable. Of course if you want to spend tons of money you easily can. Also the food can vie for the title of best in Italy. Fresh, and you have not lived until you've sampled the spaghetti al fruits de mer at da Gemma. Well, virtually any food is good and reasonable.
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