The fun lies in the unknown: An itinerary can be helpful but you need not lose your sleep over it. Let your curiosity lead you in exploring a restaurant in a little known corner of the city where you are travelling or a local market which might not be there in the travel guides. Not strictly following a schedule can sometimes give you memories to cherish for all times to come. Be a gypsy at heart.
Find your own path: Get rid of the herd mentality. Just because the whole world is going ga ga over a particular destination, you need rush there. Decide your travel destination as per your interests, passion and the like. And travelling in a group might be easy and safe too but life is not all about playing safe. Travelling is about discovering your inner self.
Explore: Indulge your taste buds and discover the local cuisine. Travelling is all about broadening your horizon. Be open to experiments and allow yourself to soak in new experiments. Be observant the way people speak, the way they dress or the music played in the cafes. Use your senses to the fullest and discover a whole new world. If you are the one who maintains a journal then keep notes. This will also help you to look back with a different perspective.