Help Plan My Asian Adventure

It's Chinese New Year and once again I'm moved to plan a MEGA trip to Asia. 
I really had hoped to go before 2017, but the whole move to England, then move to New Mexico kind of got in the way. Plus there was that hurricane... 

An unexpected turn of events caused me to postpone this adventure for a couple of years, but I think it's time to start planning.

I’ve always wanted/planned to sail from California, take in the Hawaiian Islands, then on to Australia, Singapore and end up in  Japan. I know that's vague AF and a whole lot of land to cover. I have a friend in Maui I'm gonna spend a week with before moving on to the land down under.  I'm trying to allot as much time as I can for exploring there. (2 months? 3 Months?) Then spend six weeks in Japan.  And that’s where you come in. Since I have no itinerary, I thought you could help plan my trip.

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I also need some logistical help:
I want to avoid flying and take boats and trains as much as possible. If anyone knows the best routes, please let me know. I want to stay away from the tourist traps and really see Australia and Asia. If you visit here much you know I'm an 'off the beaten path' type traveller. I like to eat local and stay in holiday houses over big hotels.
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If anyone has traveled through the region this way before, I’d love to hear about your experience and pick your brain for information.  You can email me msoneworld4me@gmail.com or leave a comment below and we can chat.

The rough plan is to spend 5 months in late 2020 having this amazing adventure. (Why does that sound so far in the future? It's only 2 years away!) While is this a huge trip, with lots of planning I want the pace to be slow and relaxed so that I have time to really enjoy the experience. 

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How long should I plan to be in Singapore?

Lastly, if you live in the region, I’d love to meet up, so leave information on how to contact you (if you want to host my friend and me, that would be super, too!) 

I’ve been dreaming of a big Asian trip for many years.  Japan has always called to me and there are so many places I want to visit.
Who knows what this trip will bring?! 

​Speak soon~