It's something I often do on trips. To do ALL the resorts does take a long time, as others have mentioned. With a car, it makes it easier - although I will say there is something to be said for exploring with a bit of Disney transport (non-bus).
For parking, one way around it is to simply say you are meeting folks at a restaurant that doesn't take ADRs (like Beaches & Cream).
An "itinerary" I might suggest...
1. Start with the Value resorts, since their themeing is more fun, but admittedly less. Just tell them you are getting breakfast at the food court ("Intermission Food Court" for the All Stars, "Everything Pop" for Pop or "Landscape of Flavors" for AoA). You can park at one of the All Stars and walk to the others. And, you can park at either Pop or AoA and walk across the pond.
2. Next, head over to Coronado Springs and then Caribbean Beach. Again, more "breakfast" to be had at the food courts ("Pepper Market" for Coronado and the food court at Old Port Royale for Caribbean Beach).
3. Next, drive over to Old Key West and explore around (Olivia's is your restaurant here, although you "don't have a reservation"). The other option is to just drive to DTD (see below) and catch the boat over and back. It takes a little longer, but it's a nice boat ride.
4. Then, drive down the road and park at DTD near the marketplace. Take the walkway over to Saratoga Springs and wander around. Then, return to DTD and pick up the boat launch to Port Orleans Riverside. I really think the DTD boat ride is a really great way to get a intro to POR. After you explore Riverside, walk along the river down to French Quarter. Then, pick up the boat back to DTD from French Quarter to grab your car.
5. Next, head over to Beach Club, telling them you are meeting folks at Beaches & Cream for ice cream. You can wander Beach Club, Yacht Club, Boardwalk, Swan and Dolphin all together. It's my favorite "cluster" of resorts.
6. Take the long leg of going out to Animal Kingdom Lodge. Mara is a good restaurant without reservations here. It will likely be evening or starting night at this point, and AKL looks beautiful at twilight and night.
7. Make a quick pit stop at the Fort Wilderness Campgrounds, if you want (although there isn't much to the actual "resort" itself). Crockett's Tavern is your place here.
7. Finally, drive up to the Poly, saying you are meeting folks for a drink at Tambu. Explore Poly for a bit, then grab the monorail to Grand Floridian. Explore there next and then head around to Contemporary. (Be careful with Contemporary. The Bay Lake Tower has very controlled access, so you can get stuck places. I would suggest exploring the main tower, then take the ground floor path (not the sky walk) to the main Bay Lake Tower lobby. The pool area is also restricted, and you can get stuck outside. Last but not least, take the monorail back around to Magic Kingdom and catch the boat launch to Wilderness Lodge. At night, this boat ride is extremely peaceful, and the pier is a really nice area. Wilderness, while nice during the day, really stuns at night. The boat launch pier brings you right up into the courtyard. On the other hand, if you'd rather come in the main lobby, just take the monorail back to the Poly to grab the car - and tell them you are meeting folks at The Territory Lounge.
So much fun!!!
