After trying and failing to put together an itinerary/award strategy, I thought I might draw on the wisdom of this esteemed crowd to see if anyone out there could help me.

I am trying to plan a Maldives trip for two sometime late next year/early 2014 and would like to book as much as possible through miles/points. My trip options (timing, airline choice, etc.) are pretty open at this point, but I am shooting for premium cabin tickets and some kind of over-water accommodations. Willing to pay an upcharge for the latter if needed.

For hotels, I've been thinking Conrad Maldives Rangali Island, Park Hyatt Maldives, or W Retreat & Spa Maldives, but only because I have mid-tier status in those programs (SPG Gold; HHonors Gold; Hyatt Platinum). I'm certainly open to other options.

Credit is good, with very few inquiries and only one card right now (Chase Sapphire Preferred). Other than ~150,000 Chase UR points, my points balances are not very high and are spread across a few programs (40,000 HHonors points; 50,000 US miles; 10,000 SPG points). Not much anticipated paid travel between now and the contemplated trip.

Anyone see a path to doing this? I'm struggling to figure out a way to do both air and lodging without needing ~400,000 points, or alternatively how to earn that many points over the next 18 months or so.

Thanks in advance for any suggestions!