I think you are doing things that are different enough that you will not be bored at all. You are likely to need 2 full days @ Mesa Verde to experience everything there including Wetherill area of the park. Stay at the Lodge that is in the park. The Metate Dining Room in the lodge has better than average food for a national park.

I like Moab/Canyonlands/Arches far better than Monument Valley. You will need a full day there though, and to get the most out of it you will need to hire an Indian Guide(otherwise your just going to see a tiny bit). The hiking in the areas you mention is far far different than hiking in the Rocky Mountains and most of Colorado. If you/he is adventurous consider www.deserthighlights.com in Moab. Totally awesome.

The Moki Dugway and Goosenecks of the San Juan are two pretty cool things to see/do between Monument Valley and Natural Bridges. Be sure and do the hike all the way down and stand under Sipapu Bridge at Natural Bridges. Truly and awesome span. You are likely to need pretty much one full day in Arches National Park.

Finally, on you way back(after Moab), consider stopping at Goblin Valley State Park and right nearby is Little Wildhorse Canyon . Both are as spectacular as anything in Utah.

Far View lodge is a very good place to stay to explore Mesa Verde, as the road in is fairly long and winding and you might meet animals after dark. The food there is fine too.

For Canyon de Chelley, do get a Navajo Guide to take you into the canyon. You can do stops at overlooks on the rim, and hike down one trail to White house ruin, but you can not visit most of the canyon without a guide in a 4 wd vehicle. You can get one to take your family on your own for a wonderful look at the area.

I might consider starting the trip in Moab, since it will be June and getting hotter as you get into late June. I would plan on at least 2 or 3 days in that area. If DS in interested in rock art, there are some very nice sites in the Moab area, the VC at Arches has maps for where to find them locally. I have some pictures of some of them at www.flickr.com/photos/emalloy2009 if you are interested. If you click my name here you can find some TRs from adventures in the area.

See what is available in terms of lodging in Moab and Mesa Verde before you decide for sure which direction you will head first.

Kayenta is a fine base for Monument Valley, but you probably would not need more than a day or less there. The McDonalds there has a nice display on the Navajo code talkers.

There isn't much in Bluff (a couple of motels, etc.), but there are lots of less developed places to explore in the area. You will need good map skills or a guide to find some of them. The Comb Ridge is an interesting area to explore.

Natural Bridges in an interesting contrast to Arches (Bridges and Arches are geologically different formations) and has some nice hiking opportunities. Unless you hike a lot, it will take less than a day to explore it.

You probably know that the parts of Arizona that are Navajo Reservation (like CdC) are on Mountain time and the rest of Arizona is on Pacific time. This sometimes matters in terms of when things start or close.

Are you familiar with Tony Hillerman?

If not, pick up his first book on the Navajo tribal police, "The Blessing Way". His series of 18 books are wonderful reads.

If you have the time, detour a bit to Four Corners, just for the heck of having stood there.

Everyone always says Four Corners is a hokie tourist trap. I am like easytraveler. I kinda like it. Does make for an interesting photo too.

A really great book to read on the area and the Ancestral Puebloan culture is "Cowboys and Cave Dwellers" about a group of amateur archeologists who figured out where the objects from the various Wetherhill collections came from throughout Grand Gulch. There is an awesome museum outside of Cortez (in Delores??) that features many objects from the Wetherhill collections and info on the family. See Mesa Verde first because it will provide so much information on the ancient ones. I personally preferred Chaco Canyon to Canyon de Chelly. Chaco is truly amazing!!

You can hike into Grand Gulch from the Kane Gulch Ranger Station. In a day, you can get far enough to see a couple of amazing sites and its easy hiking. You do have to hike to see some of the best sites! And the far flung sites are, in some ways, more amazing than Mesa Verde--you can see finger prints in the mortar!

I would also skip Hovenweep. You can do a neat driving tour of rock art around Moab--it was very interesting. The Natural Bridges Monument is a great day hike.

Thanks for all of the helpful replies. Just to be clear, I know that the geography of where we usually hike and spend time in Colorado (Denver, Summit and Eagle counties) is much different than the areas we'll be vacationing - what I was wondering, and has been answered by emalloy, was whether the places and sights on this trip were too much like each other.

On Monument Valley, it's not my first choice, either, but it was DS's top choice, due to his interest in films. (When in NYC last year, we visited a bunch of film locations, including Serpico's apartment, the final scene in Taxi Driver, etc. - it was actually fun.)

emalloy, especially thanks for the links to the pictures. It sounds like our interests are similar, in terms of beauty and petroglyths.

We will be traveling near the beginning of June, but the point about heat in Moab is something to consider. I also need to consider late-day traffic back to Denver on our return day - it may make more sense to reverse the trip order for that reason as well. As of right now, both The View (Monument Valley) and Far View (Mesa Verde) have availability.

Four Corners - DS has already said no, and we can't do everything, though it looks like our tentative route would go right through it. (I visited it as a kid, and DH doesn't care).

Canyon de Chelly - I've already told the family that it makes the most sense to have a Navajo guide here. Would be nice to have one in Monument Valley, too, but we'll have to see how that works out.

Any more advice about how many nights in each place? Now I'm thinking 1 night Ouray, 2 nights Mesa Verde, 2 nights Canyon de Chelly, 1 night Monument Valley, 1 night Bluff (Natural Bridges from here?), 2 nights Moab. Or the reverse. Does it make the most sense to visit Natural Bridges on the way from Bluff to Moab (or the reverse)?

And yes, both DS and I have read several Tony Hillerman books!

You already have many wonderful places on your itinerary. I'll add another fascinating stop for your consideration since you're thinking of going as far south as the Canyon de Chelly--the Hopi mesas, in particular, Walpi, www.experiencehopi.com/walpi.html.

We loved Far View Lodge (not so much the room which was on the very rustic/basic park lodge side of things but the location, ambience, experience were terrific) and we enjoyed several wonderful meals at Metate including a memorable birthday dinner.

In Monument Valley, we stayed at Gouldings Lodge and both of us enjoyed the Navajo led tour of the valley including somewhat hokey but great photo opps and terrific memories. I have some lovely sunset photos and classic red rock photos from this stop.

We didn't make the rest of your itinerary as we started with Grand Canyon and from Mesa Verde headed to Santa Fe.