If you enjoy relaxing by the pool with gorgeous views and you have money to burn at Capri's splendid Shops this is the Island paradise for you. Capri town is stunning and the "Shopping Path" is pristine, peppered with fine shops and five star hotels, it reeks of elegance. More humble Anacapri is elegant with a twist on commonality, more the locals spot but very enjoyable. For me shopping like this is torture but professional shoppers like my niece, my sister-in-law and my friends the Weakley's this is Heaven on earth. They can ploy away hours browsing and picking through designer shops just to be certain they step off the plane in America looking like movie stars. I recall having purchased my first pair of Prada sunglasses in 1991, I paraded around Italy looking like George Hamilton and when I got off the plane in Washington DC I looked like Shecky Green in an Altman movie.
The quintessential hotel in Capri is the Hotel Quisisana where everything is perfect, www.quisisana.com, the only bad thing about the Quissey as it is affectionately called by its pretentious, snooty guests are the guests themselves. Threat yourself to a cocktail there at their bar and terrace on the Shopping Path.
I spent four days on Capri several years ago and stayed at Da Gelsomina all Migliara, dagelsomina.com in their five room hotel! The rooms were small and very simple but the people there are awesome and the restaurant serves the best food on the Island and maybe Italy. Vegetables picked right from their gardens, wine from their vineyard and fresh pasta made every day by their grandma's! They have a gorgeous infinity pool that over looks a spectacular view of the sea. They apparently sell memberships to their pool, remember they only house 5-10 guests, because there are many locals there enjoying the weather and the awesome pool. They also serve a light lunch in season at the pool and a full lunch in the restaurant. Be sure to make a dinner reservations or you won't get in, and say hello to Gelsomina and Pasquale for me. The charming people at Gelsomina will pick you up in Anacapri too.
The Blue Grotto is a must see for you no matter what your age. The boat ride is fun and the grotto is like nothing you have ever seen. If you are so inclined you can dive off your boat and swim til your hearts content. There are boat rentals for just tours with groups, privately or you can rent your own boat at Marina Grande.
Buy your round-trip tickets to Capri the day before you leave from the kiosk at the ports in Sorrento, Napoli or Positano and plan to return on the second to the last boat. I've heard many stories of the last boat being cancelled and people having to scramble to get a hotel room for the night.