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thats great youre off the Sacred Music Fest! ive been looking at going each year past few years and still not ended up going - other things keep cropping up but each years line up have looked very enticing!

Id probably do the trip pretty much that way Ive written - grab a Michelin map and check out the routes - half reliable marking of the scenic routes in green on it but you get an idea anyway - probably take the local roads rather than the freeway - for Rabat and Sale bit to Larache anyway but if you want do from Casa to Rabat by freeway but local road is better for seeing more of Morocco.

the route down from Chefchaouen to Ouazzane is scenic.

Rabat and Sale could easily keep you busy for a couple of days if you are into archeology and history - and along the road north are botanic gardens, a private museum and some lovely beaches that you can check out as you go along
Ive stayed with connections whenever stayed in Rabat so not up with accomm there....but this is what I did like about the LP for at least having some accomm tips that turn out to be gems in amongst finding those from locals when you get there....its been Moroccans that got me to check out the Footprints for in their opinion the better range of local establishments written into their guidebook that i got one but ive not really needed a guide book for accommodation for a number of years now - other than for phone numbers from time to time.
the DK eyewitness guides are great for historical info to accompany the sites inc maps and walking and driving routes to see sites.

we were going to stay a night at Moulay Bousselham one time but didnt but at least found out that there are a number of apartments available and they werent expensive, though June when youre there is going to be the beach side holiday season. It was a case as is usual in many places someone appears and approaches you to see if you are looking for somewhere to stay and will show you whats available and you can negotiate a price.

otherwise Ive stayed at Asilah quite often and always just got an apartment by finding the usual persons that had previously approached us to see what apartments were available and having a look at whats going - theres a lot of apartments in Asilah both in the medina and outside but was one of the cheaper places to stay when travelling around MOrocco.

Over at Chefchaouen theres an abundance of places to stay there too - Ive stayed at Hotel Andalous which was cheap and done up in really colourful andulucian style. but had usually stayed at the kasbah restaurant hotel a few times and another place Ive forgotten the name of but theres loads of choice so probably just have a look around when you get there - locals will approach same thing to ask if you want somewhere to stay. just always have a look before you say you will take it...check for signs of bed bugs and the state of the bathrooms etc lol!

see if theres any interesting sounding places in your RG or Footprints...

Im in NZ at moment and in the throes of moving onto sort a few things in Sydney and then a few weeks from Singapore on the way - basically trying to get back to London in time to get to Morocco by the end of the first week of April to see the apple blossoms and be in the desert for the end of the Marathon des Sables and then head up to Casa to fly to Senegal. Thanks for pointing out the travel warning for Dakar - will see what my connections can find out.....

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But, if you come back in June so maybe it would be better to do this Rabat etc. then, in June it is warm so better to stay at North than at South.

And in May those 5 days you can spend around Marrakech, visiting Essaouira for example, or Taroudant which is very nice city, more calm than Marrakech. 5 days are not so many days in Morocco, the time is only flying :) you know.
It is my suggestion, so ... have a nice in any case.

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Thanks to everyone for the suggestions! Khamlia, you make a good point about the weather. Won't the desert be hot in June also? That is why I originally thought to go to the desert in May, but perhaps it is better in the desert in June than in southern Morocco?
So many places I want to see, such difficult decisions!

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This, regarding weather, looks useful.
http://www.weather-and-climate.com/average-monthly-Rainfall-Temperature-Sunshine,merzouga,Morocco

The months March, April, May, October and November have a nice average temperature.

I think that even if you go to Merzouga/Erg Chebbi in early May, you may find it quite warm. Khamlia can advise you better on this, as she has more experience there than I have.

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Babeelemonade, the desert is in the south, and I can tell you that where I live in Taroudant it can get hot in June, and I'm nowhere near the desert!

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Yes, it is difficult to make decision, but please, take it easy. In Morocco driving is slowly and there are so many beautiful things so it would be only pity to only run around.
The desert in June - maybe it can be hot, maybe not :) I was there once in June and it was 42 degree. Last year I was there middle of May and it was around 37 degree. One other May it was only 34 degree. So you see, it change every time. If you decide to go to the desert, be prepared for hot weather. But hot can be in Marrakech too.
Don' t only do the desert trip when you have only 5 days, it would be waste of the time can I say.

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P.S. and as David says, in Taroudant can be hot too

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My apartment is on the top (3rd) floor of a building in Taroudant. In winter it's like a refrigerator and in July/August it's like a Hammam. The walls are thick and absorb the heat, so even in the evenings when the temperature outside cools down, my apartment is still sometimes very warm. At those times, I can just take a sleeping pad out onto the roof of the connecting building and sleep there under the sky!

I like it, and I don't want to move! For this apartment, a large one-bedroom, I would have to pay 5 times as much or more where I come from in Canada. A long way to go for affordable housing!

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Thank you all for your input; I think I have managed to narrow down my itinerary for my first 5 days in Morocco.

I will do Marrakech - Ait Benhaddou - Taroudant - Essaouria - Marrakech

I was originally planning to do it in this order, but am wondering if the drive is easier the opposite way?
I'd like to drive to Essaouria near the coast, via Agadir, is this a feasible drive?
(I'm waiting on my guide books and maps to arrive in the mail, but in the meantime I'm getting anxious.)
I hope this sounds like a good plan.