Many Australians love to visit the Indonesian island of Bali, and many were stranded in Bali due to a volcanic ash cloud that caused the cancellation of flights for several days. I must admit, like most Australians I have been to Bali, however as you know, I prefer Fiji or Hawaii. The event illustrates why you need travel insurance, because it can be quite costly to over stay a trip, as many people just budget for a certain period of time. Actually sometimes the best holidays are completely unplanned like one of our trips to Fiji when we lost an engine over the Pacific and had to turn around. We ended up staying an extra four nights and had a great time.
What I've learnt travelling and planning operations in another capacity is that things rarely go to plan, Murphys Law or what Clausewitz called, 'Friction', is always present in any human endeavour. People are unpredictable, they make mistakes, they make the wrong booking or they even can't fix jet engines that stop over the Pacific! I wasn't flying Qantas that time, but Qantas pilots are often ex military so they are adaptable, particularly once famously landing a jumbo with no engines in Singapore! The main antidote to 'Friction' or Murphsy Law is experience and adaptability, and of course cash, credit and insurance. Having $100 USD can get you out of a lot of trouble in most parts of the world, everybody accepts US dollars in my experience.
In conclusion rather than trying to develop, 'the perfect plan or itinerary' you should really be thinking about how can I become more flexible to react to opportunities and get around obstacles that life throws at us. Of course its much easier now with the internet, because you can buy transportation and accommodation with your credit card. In addition you can learn from the experience of others by looking at reviews on Trip Advisor or travel blogs.
