1. Start with your destination in mind. You need to decide where you want to go. Do a little research and see if you can go during the shoulder or low season. When you go can make an enormous difference in terms of cost and how crowded the destination will be.
2. Determine your budget, this includes cost in miles, points and cash/credit. If you want to travel to Hawaii visit a site like awardhacker.com and find out how many miles you'll need to get there. Then see if award space is actually available for your desired dates. You should also do a bit of research as to which airline offers a better flight experience.
Awardhacker will also help you figure out how to search for space availability. It lets you know from which of the rewards program you can transfer points to miles. Last, it also offers information on how to redeem points/miles for tickets.
Getting there is just part of your budget, you can use awardmapper.com to find out your hotel options with points. A big note of caution: knowing how many miles and points you will need has nothing to do with availability. You may have all the points/miles in the world, but if there isn't award space on your desired flight or your dream hotel doesn't have award nights on your chosen date, there's nothing you can do. In my case, I would research what are the best Hyatts and Marriotts on this list.
3. With this information you can develop your points and miles strategy. Continuing with the above example, you would either need 60,000 Ultimate Rewards (UR) or 50,000 Starpoints (you get an extra 5,000 for every 20,000 you transfer to partner airlines). In this case, you could even combine URs and Startpoints. Let's suppose you already have 40,000 UR points and another 20,000 Starpoints and want to travel to Hawaii in business class from JFK. It would make sense to transfer 20,000 Starpoints which would become 25,000 SkyPass miles and 35,000 UR points which would total the 60,000 miles you needed. This kind of pooling is not always possible especially if you are dealing with let's say Citi Thank You points and IHG points. Starpoints for instance are super valuable due to the fact that you can transfer them to about 30 different airlines. The big downside of having the SPG card is that you earn up to 5 Starpoints at Starwood Hotels and 2 at Marriotts, but only 1 Starpoint on everything else. URs can be transferred to four hotel programs (Hyatt, IHG, Marriott and from Marriott to SPG at least for now, and Ritz-Carlton) at a 1:1 ratio.
You can also transfer URs to seven different airlines.
If you already have points spread around the four major point currencies i.e. MR, UR,TY and SPG for your trip to Hawaii, it might make sense to consolidate your points by transferring them to Singapore Air or Air France.
While it's true that it would cost 15,000 more miles, this post is not about hoarding points, but rather taking that amazing trip to Hawaii! Once again, keep in mind that you need to check award space availability as Award Hacker recommends, and if you find what you're looking for do not hesitate!