For someone unfamiliar with the particular road I would stick to daylight if possible.

I should clarify that major roads like interstates are fine, but roads like AZ 86 and AZ 77 are much more questionable.

AZ Routes 85 and 86 have some really outstanding views between Ajo and Tucson. The Tohono O'odham Nation covers some truly beautiful desert west of Kitt's Peak. My daughter once said, "It is like a Road Runner cartoon!" when driving there. Both roads are in good condition, at least they were last year - ignore TripAdvisor.

Route 286 down toward Baboquivari Peak is also fantastic, especially in the very early morning with the sun on the mountain. As Lost says above, though, these aren't highways, they are state routes like any other in Arizona. Also, being on the rez has no relevance as to whether they are safe or not.

At night I would drive much, much slower (if at all) on these roads because of the risk of hitting someone walking across the road or hitting wildlife wandering around. Furthermore, if you ditch you may wait a long, long time for anyone to come along who can help you get back out.

Hmm, this is very helpful. Everyone is consistent about not driving on these roads at night. I have two options I am considering:

1. First night, leave PHX at 6pm and drive to Ajo and overnight there. See Organ Pipe the next day (start early) and the drive to TUS at the end of the day and try to get there before night fall. Spend the next 4 days doing the stuff around TUS.

2. Skip Organ Pipe completely and just do 5 days in TUS.

The people on TA seem to be leaning towards option 2. Is Organ Pipe worth visiting or should I skip?

Organ Pipe is unique and has some great walking and hiking and bird watching, and it is glorious when the desert is in bloom. On the other hand, the temperature and the Border Patrol can really make it a miserable place, depending on the time of year you visit.

If you can get there in the winter or spring, and you like hiking, it can be well worth your time to go down 85 and spend some time at Organ Pipe. In the late summer it can be hot (duh). Just the drive down 85 is pretty cool, and if you decide to get out and hike, great. However, people often claim that this is the only place to see organ pipe cactus, which isn't true - my neighbor next door has some, as does the guy down the street.

A word about the Border Patrol. For some reason I have had some weird experiences with them, and so have my hiking and birding buddies, in and around Organ Pipe. Despite the fact that we are the most obvious tourists from the valley you could ever see, we have been stopped and questioned multiple times on route 85 on a single trip, and this isn't unique. Adding to the frustration was that these were not at alll positive interactions. Further other things we saw on that same trip indicated that the BP was utterly wasting their time and our tax dollars just hassling people at convenient spots rather than actually doing their job. In any case, [removed OMNI/PR political characterization/argumentation] in that part of the state, so be prepared to be stopped, to show identification, to prove you own or have rented your car, to answer a lot of damn fool questions, and to generally waste a certain amount of time. You may experience the same sort of thing if you visit the Sierra Vista area or Bisbee. Rant over.

Hmm, I'm going at the end of this month so the weather should be good and I don't mind dealing with the Border Patrol. But I'm wondering whether I should go to Organ Pipe this time or leave it for another trip - it's out of the way, I'll be alone, it'll be a long day, maybe driving after dark, etc. I'm leaning towards leaving it for another trip - mostly because I'll be by myself so if I get stuck...but am open to be swayed otherwise.

Thanks for all the advice!

The cacti generally bloom in May, so I don't think you'll see that. We have had some abnormally warm weather the past couple weeks (mid 80s), so you might see other plants blooming.

If you're coming from the east coast who knows if you'll get another chance to visit Organ Pipe. I say do it. It's just a couple hours from me so I can always put it off (and then I never get around to it :D).

As far as the border patrol, there are a lot down there (like every other car). I've never had a problem at the checkpoints; it's usually one or two random questions that give the nearby drug dog enough time to take a quick sniff. The longest I've spent stopped in one was maybe 10 seconds. I've never once had to show ID, reg, etc...

Okay, thanks. I think I might go.

BTW, any recommendations on what part of TUS I should stay in? Just considering that the things I want to see are all over town...I will probably be airbnb-ing.

The north side (towards Mt Lemmon) or the east side (towards Saguaro East) are very nice. The area around UA isn't too bad either, and is more centrally located. Parts of the south side can get a bit questionable.

Tucson sucks to get around because for many destinations you'll need to drive miles and miles of city streets, and Tucson is the pothole capital of the world.

One other random note since you'll be doing a lot of outdoors stuff: The Oracle Control Road that goes from Oracle up the northeast side of Mt Lemmon is a high clearance 4WD road. I've heard of some GPSs giving directions up it, so don't use it (it might even be closed this time of year).

The Catalina Highway (the main road from Tucson) up the south side of Mt Lemmon is paved and fine for all vehicles.

I once stayed in a motel in Ajo because I was going to Organ Pipe Cactus National Park. The motel was worse than terrible. There is one nice place in the former copper company president's house. The town's main purpose is to sell insurance for going into Mexico. Ajo has the hottest weather in Arizona and the adjacent part of Mexico has the hottest temperatures in Mexico despite its northern location. There was nothing particularly scary on the road into Ajo, day or night. I would stay along I-10 and go in for the day. My favorite places are a bit east of Tucson - Chiracahua National Monument is spectacular with great trails and a morning hiker's shuttle (reserve in advance). Then there's Fort Bowie, Grapevine Canyon Ranch, Cochise Stronghold and the Amerind Museum. You can also see incredible gatherings of birds to the south of Pearce...then there's Rodney's Barbeque in Willcox - the highlight of any trip... after you've been to Kartchner Caverns.

Pothole Capital!
 

Well, at least the capital of the Southwest. I've been to Philadelphia. And Manila.

5 days around Tuscon
 

Has anyone visited the Titan Missile Museum and silo near Tuscon at all, and is it worth going out of the way to visit if in the area?

I was just there Super Bowl weekend. Really fun, a nice tour of the underground complex that occurs hourly, delivered by former Air Force vets who actually conducted shifts in these Titan silos. Hourly tours have about 10-12 in the group and I swear I was the only American - lots of British/Australian accents. Recommended.

5 days around Tuscon
 

Thanks Brian. Will have to pencil in a side trip to Tucson some time when I'm in the US.