I would absolutely do Italy again. I spent a month in Europe after college and it was an amazing time, social and culturally. I was in Florence back in 2006 when Italy won the world cup and the city went nuts. Rome is a great place to base off of. To get cheaper flights, consider flying into some of the other cities in Italy (Milan, etc.). There's so much to do in Italy from beaches to art to food to clubs. Places I would absolutely go: Florence, Venice, Rome, Cinque Terre. Sandals type of resorts arent my cup of tea and i really dont find enjoyment in sitting on the beach for 5 days straight.