Travel Requirements - A major concern is bureaucracy. Every country has its particular set of rules. For example, in some places you have to employ an agent to do the check in for you (in comparison, in the French islands in the Caribbean you sit down at a computer and do it yourself -often for free). In French Polynesia you can only stay for 90 days without getting what amounts to a French residency visa. This is a bit of a problem since FP is very lovely and immense with many places to visit. Also, you have to put a bond here to insure that you will leave - it amounts to the cost of a one-way ticket from Tahitito your own country (in our case to Vancouver) for each person. This would amount to more than $4000 and you get it back but it is complicated. In the Galapagos you can only stay for 21 days without spending literally several thousand dollars in fees. The Panama Canal has its own set of issues. The agent's fee is more than $500 and there are fees for everything including fumigation (they don't actually fumigate your boat, they just charge a fee for a fumigation certificate). It seems that major parts of the economies in Spanish-speaking countries, are administrative busy work.
Travel Planning -Much more enjoyable is planning the trip and finding out why we absolutely must visit places that we had never heard of such as Suwarrow (many spellings are used) Atoll in the Cook Islands http://en.wikipedia.org/wiki/Suwarrow . The result is our plan to go backpacking in Ecuador/Peru and visit some of the tiny atolls in the Pacific. We have four Lonely Planet guides along with several cruising guides.
Stuff! - Finally a lot of time went into looking after all of the minutiae that will make the trip more enjoyable. One example is that a couple who did the backpack trip in Peru said you must have ear plugs since they play the music so loud. I can appreciate this since similar conditions existed on the minibuses in Lesotho that I used a lot when I was there. The volume was way beyond what the speakers were designed for so it was very nasty, but there the trips were at most an hour - some of the ones in Peru will be many hours -so time was spent on finding the little package of ear plugs we now have. June has been spending many hours loading music and audiobooks onto our IPOD. We found in the Caribbean that an IPOD was a wonderful tool for the midnight to 4 am watch under the stars.