Try to get to Dead Horse State Park...beautiful

Two biggies you are missing Dead Horse Point and Mesa Arch.

Do Mesa Arch at sunrise to get the best photo. We did Delicate Arch Hike in the evening at Sunset. There were a lot of people, but I think it might be better for a sunrise photo. This was the only time we encountered very many people in the park.

Be sure and get your fiery furnace tickets early in the morning, they may even allow it the day before, check their website to make sure. They only take 20 people per day(i think that is the number anyway).

Do not miss Double Arch and Balanced Rock in Arches. Probably allow 45 minutes at both of these stops. Double O is different than Double Arch. Double Arch is probably my all time favorite arch.

Do the canyoneering with Desert Highlights over the flight. We did both and we are going back for more of the canyoneering. Several of their hikes are in Fiery Furnace, so you might want to do that with them and then you wouldn't have to worry about the park service fiery furnace hike. We did Krill Canyon which is in the fiery furnace and is the hardest hike that they offer. It was our first time canyoneering, and I didn't think it was that hard. If you are able to hike Devils Garden you would be able to do the canyoneering. I would hike to Delicate Arch and Devils Garden before the canyoneering. Once you do it, I can almost guarantee you will be starved for more canyoneering. They do this in Oregon as well (it isn't on their website yet) and we are doing that next summer with them.

There was one restaurant in Moab open for breakfast only. It was good. We ate at a place for lunch that sold sandwiches and oriental bowls that had a strange name and found it to be a good choice for lunch. I am blank on the name of both of them. The rest you have listed are good to try for a nicer relaxing dinner.

Jailhouse Cafe you have listed is the place for breakfast I was thinking about.

Hogi Yogi was the sandwich and rice bowl place. Moab Brewery we found to be good. Ok that was my last multiple post. Sorry. Habe a great time!

Thanks TAW and Spiro.

Dead Horse Point looks like a no-brainer. Don't know why I left that off the list, and assume that we can do it going either to/from Island in the Sky. What's a reasonable amount of time for Island in the Sky, including Mesa Arch and any other shorter hikes in that area?

1.5 days for the 3 Arches hikes is reasonable and gives you time for stopping at some of the other arches. Time of day depends on how important good light is for your photography. The iconic photos of Delicate Arch are at sunset, but the view is impressive no matter the time of day. If hiking up for sunset fits your plans, do it but don't feel you have to arrange your itinerary around that.

I'm a bit concerned about your total time - 1.5 days at Arches, plus a day for Island in the Sky plus another day for Chesler Park leaves you with half a day for everything else. Definitely combine Island in the Sky with Dead Horse Point SP - Mesa Arch at sunrise and Dead Horse Point at sunset are prime times for photos. (Sunrise is ~7am and sunset ~7:15pm right now in Moab)

I guess if I had to cut something I'd consider cutting Devil's Garden. That would give you an extra half day somewhere else and allow you to get through Arches in a day (as long as you can get Fiery Furnace permits that fit your schedule). You can hike to Landscape Arch along the Devils Garden trail if time allows. In order to do Delicate Arch at sunset, you have to do Fiery Furnace in the morning. I don't think you'd have enough time after the afternoon Fiery Furnace hike to drive and hike up to Delicate Arch before sunset.