Mary, your plan to relax by the pool when the afternoon is warmest, and the crowds at the parks tend to be the thickest is brilliant! Regarding taking Walt Disney World Transportation versus driving, I think it depends on a number of factors. The Wilderness Lodge (WL) has a great location and two excellent (albeit very different) full-service restaurants. My husband and I ate at
Artist Point about a year ago and thought it was fabulous! Whispering Canyon Cafe is fun for a crowd or family. If you are dining at WL, the Contemporary or any of the restaurants at the Magic Kingdom, I would recommend taking one of the resort boat launches to your destination. They are convenient and run regularly. Similarly, if you are dining at any of the other resorts on the monorail (Polynesian or Grand Floridian), it's easy to take the boat to the Contemporary and quickly jump on the monorail to your destination. If your are eating at another resort (at
Jiko at the Animal Kingdom Lodge, for example), you may find that driving your own (or a rental car) is quicker and more convenient. If you are dining at Epcot or Hollywood Studios and plan to explore the parks before/after dinner, I would probably take Disney transportation. However, as a guest staying on property, you would not need to pay theme park parking, so driving is also an option if you prefer to do so. Bon Appetit!