I just did a very similar trip last month and posted
some thoughts and pics here -
The Burr Trail is great. At the top of the switchbacks, take the turn into Strike Valley Overlook. It's a short but slightly technical drive in, maybe a mile or two. At the parking area you can hike out to the Waterpocket Fold overlook and oh my goodness, what a view... Back on the trail, just past the overlook, I would also recommend the Wolverine Loop Rd, a 28 mile 4wd trail that starts on top of the Burr Trail, just past the switchbacks, where the road turns to pavement, and it rejoins the Burr Trail near Boulder. That was a fun track through petrified forests, scenic views and canyon driving.
I would skip Hole in the Rock, unless you absolutely have your heart set on driving over washboards and beating your truck and kidneys to death. A better alternative IMO, is the Smoky Mtn Rd, It's is a phenominal drive from Escalante, down to Alstrom Point. Eighty miles of nothing but dirt, solitude and incredible views....
When in Boulder, eat at Boulder Mesa restaurant or Hells Backbone Grill for a nice meal (not at the Boulder Grill). Kiva Koffeehouse on Hwy 12, just west of Boulder is a cool stopping point. They have great baked goods and coffee if you like that kind of thing. If you have time for a 6 mile roundtrip hike, you could check out Calf Creek Falls, between Boulder & Escalante. The trailhead is clearly marked on Hwy 12.
If the weather works with you, you should be in store for a great trip. I hope you'll follow up with some photos afterwards! Be safe -
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