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Hong Kong & Indonesia (Java, Bali, Komodo, Gili/Lombok) HELP!

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Dear Fodor's Forum Members:
Please help me plan our dream first-time to Asia trip!  I am going on a dream trip to Hong Kong and Indonesia in about a month.  

We are experienced travelers to other continents, but have never been to Asia. We have some sophisticated tastes being that we live in downtown NYC and are fond of luxurious elements; however, we always try to stay at the most unique and exotic place possible for the least amount of money (caviar tastes at tunafish prices).  We prefer to stay at some cool hip unique antique-filled palace for a dime.  I wish we could afford $300/night hotels, but we cannot.  

We are hoping to stay some night very cheap but great places for Under $100 and other nights between $100-$200.  We may splurge slightly higher for a few nights here and there, but prefer stylish at low cost..

And we love nature and wild places, adventure, cultural experiences, historical structures and architecture, hip laid back bars, fabulous food, cool fashion, and cool village markets where you can buy unique items at a bargain.  

Here is my tentative itinerary.

Sept 25 Leave New York  - Cathay Pacific Business Class

Sept 26 Arrive in Hong Kong at 5am
--- is it a pain with luggage to take the train from the airport?
--- we would like nice hotel suggestions. I am looking at Intercontinental in Kowloon because I thought it might be nice to lounge at their famous pool before checkin because we might be tired.  It is slightly out of my budget. I also thought to inquire at the YMCA because it has a good reputation as an unusual budget lodging.  
---  We like old authentic building, architecture and natural beauty
---  We are kind of foodies but will eat inexpensively too. 

Sept 27 Hong Kong
---  I think there is a boat Star Ferry to see Victoria Mountain, but I need suggestions.  What should we do?
---  We may want to get clothing made or shop in old exotic markets.

Sept 28 Hong Kong
---  Need suggestions

Sept 29 Fly to Singapore at 8am.  Change Cathay Pacific plane to Singapore Airlines/Silk Air to fly to Bandung, Indonesia.  Do we need to collect our luggage and go through customs if we are just changing planes? We bought 2 separate tickets. Will the airlines allow us to go through? Do we need a visa for this? Our flight is 3 hours later.
--- Pickup in Bandung by car and drive 2 hours to West Garut to Kampung Sampireun Resort and Spa.  We saw this hotel on the Travel Channel with Anthony Bourdain.

Sept 30 Kampung Sampireun Resort relaxation and tour village.

Oct 1 - Travel to Yogyakarta
-- How to best get there?  Is the train worth it for the scenic ride?  Is the executive or business train faster?  Ir should we fly?
-- Where should we sleep?  High end is possible because I think hotels are much cheaper here.  If we want to see Borobudur, should we stay there to arrive early in the morning? Or should we stay in Yogyakarta?  How far away is Borobudur?

Oct 2 - We want to see Borobudur, Prambanan, some palaces, musicians, puppets, crafts, and whatever else is recommended.  Suggestions?  How much can you see in a day?

Oct 3 - Yogyakarta - need suggestions

Oct 4 - Fly to Denpassar, Bali in the morning.

We have from October 4th to Oct 17th to figure out.  We fly out of Bali on Oct 17 at 4:00pm.  Please factor in travel time to different locations.  How do we hire a driver and guide?  
(13 nights total)

Here are the things we think we would like to do:

Ubud (4nights) - I always dreamed of Ubud Hanging Gardens, but I do not think we can afford it.  We have NO IDEA what to do.  All I have heard about is some Monkey Forest, a volcano where you can have lunch, rice fields, some Hindu temple for a ceremony at night on the water, and shopping.  Please advise.

Komodo Dragons - preferably upscale liveaboard cruise (3 days/2nights) where I believe we fly into Labuan Bajo..  Komodo and Rincon.  We need recommendations on the best equipment and safest boat with private cabins, good facilities, service and good food.

Maybe Gili Islands or Lombok? (3 nights).  Is this worth it?  We may be interested for a change in pace. Concerned about travel time.

Some other town in the Bali, South (3 nights in this location) I guess, but not crazy city or big box hotels.  We like nature and maybe beach.  No high-rises or packed in like sardines.  Being that we live in NYC, we would like something completely exotic and unusual.  I think someone might have mentioned Canggu or Sanur?  We do not want to be in a non-stop party Miami or Vegas zone.  We want authentic experiences and access to cool unique shopping and beach or nature relaxation. Need place to stay.

Also, how do we lug around 2 large suitcases?  Do we need a backpack only to go on a boat or Gili Islands?  Where do we leave our suitcases?

Do we need cash everywhere?  Do we need malaria pills and shots?

Thank you so very much in advance.  I am a little overwhelmed and this is in one month.

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