5 days between LA and SF. I did this in September, SF to San Diego and back in 9 days, it wasn't enough time, there's too much to see.
my $0.02 with your 14 year old in mind...
LA - lots of amusement parks, Disneyland, Knots Berry Farm etc.
traffic can suck ass, do not drive through the middle of it ever.
we had OK luck sticking to the coast. after you pass Santa Monica it lightens up. heading north is miles and miles of state beach, no gas stations.
then Oxnard which is as pretty as it sounds but you're leaving LA at that point.
Santa Barbara is a nice college town, check out State St for shopping and stuff, that's the heart of the town. for kid/museum stuff, they have a nice Mission.
http://en.wikipedia.org/wiki/Spanish_mi ... California
this is the last stop for 'warm' water on the beaches. north of there the water gets cold.
from there it heads up into the hills, just some small towns.
Pismo Beach, don't know it, never stopped there, looked like some amazing geology though.
then San Luis Obispo, another college town, not a whole lot to see, but a nice vibe. for a laugh, eat at the Madonna Inn, your son will love the insane decorations. definitely take a piss in the bathroom, it's a freaking waterfall.
http://www.madonnainn.com/
it's right off the freeway.
then west to Morro Bay, small beach town, lots of outdoor ocean activities and a HUGE ass rock. Cayucos is a small town north of there, supposed to be better than Morro Bay, never stopped there (yet.)
north of there is pretty sparse, fill up on gas before you leave town. eventually you pass Hearst Castle. you know William Randolph Hearst? aka Citizen Kane. I've heard it described as 'once you see one huge amazingly decorated room you don't need to see 300 more.' look it up, maybe the kid would dig it, I'd skip it since you don't have much time.
then you climb up and up as you hit Big Sur, HUGE cliffs, amazing views. outstanding camping/hiking. Nepenthe is a necessary stop, amazing place and a nice break after driving twisty roads.
http://www.nepenthebigsur.com/
then north to Monterey Bay/Carmel.
Monterey Bay Aquarium is very cool, "holds 35,000 plants and animals representing 623 species."
http://www.montereybayaquarium.org/
eat at one of the restaurants along the water and you can watch the sea life in the bay, which is a national park and has a LOT of wildlife in it. you can also rent kayaks and get tours out onto the water.
the 17 mile drive in Carmel is pretty amazing. perfect coastlines and $5 billion homes, jaw dropping stuff. it's $10 to drive it but it's worth it. there's an overpriced deli with uber-Gucci food, buy a picnic there, find a spot and eat.
http://en.wikipedia.org/wiki/17-Mile_Drive
over to Santa Cruz. there's an amusement park on the water, next to the famous 'Steamer's Lane' surf spot. another college town with a downtown a kid would dig.
SF...
stuff around the Fisherman's Warf area.
Bay Cruise - get in a large boat, it goes out past the Golden Gate Bridge, around Alcatraz and back, all the while they play a recording of people telling local history. I still like to do this, even after 25 years.
http://www.blueandgoldfleet.com/
Alcatraz - very cool tour, even the locals like it.
http://www.alcatrazcruises.com/
Museum Mecanique - a pretty collection of OLD mechanical amusements, as in the turn of the century version of videogames.
http://www.museemechanique.org/
in that area I really like McCormick and Kuleto's for dinner. GREAT views of the bay and the food is decent, in 25 years I've never had a bad meal. nothing amazing but I love the place.
http://www.mccormickandschmicks.com/Loc ... intSt.aspx
(it says schmicks, but that's a sister restaurant.)
if you want f-ing amazing outstanding food in that area, try Gary Denko's, make reservations well in advance. one of the top 3 restaurants in SF.
http://www.garydanko.com/
west of there towards the Golden Gate Bridge is a cool vista, Fort Point
http://www.nps.gov/fopo/
further west and south is some amazing hiking (yes, hiking in a major city.) Lands End
http://www.panoramio.com/photo/6534176
then go over the Golden Gate Bridge, at the other side, just past the vista viewpoint, take the Rodeo Drive exit, it goes back under the road and up a hill, freaking fantastic view of SF.
http://www.panoramio.com/photo/9397581
the great view of town from the south is from Twin Peaks.
http://www.panoramio.com/photo/10461789
and finally you can see SF from the middle of the bay on Treasure Island (aka Yerba Buena Island.)
http://www.panoramio.com/photo/3982732
North Beach/Chinatown
North Beach is the Italian district, it's right next to Chinatown. it's a trip to be in one part of town, walk down Jack Kerouac Alley and you're in another.
http://en.wikipedia.org/wiki/Jack_Kerouac_Alley
Haight/Ashbury is cool, your kid will want to see that. upper Haight (west end) is for tourists, lower Haight (east end) is more locals. the corner of Haight & Ashbury is the center of town.
Muir Woods - remember the speederbike scene in The Empire Strikes Back? it was filmed here. the redwood trees are pretty amazing to see, hundreds of feet tall, thousands of years old.
http://www.nps.gov/muwo/
tip - check a map, see Market St? there's not much south of Market for out of towners, stay north of Market. the better clubs are south of Market, other than that it's industrial/commercial stuff.
as for music, I don't see anything particular with concerts on those days
http://jon.luini.com/thelist/date.html
maybe the Crystal Method on the 15th in Petaluma, which is about an hour north. I think it's a kid friendly venue, only time I was there was to see Primus, a show that ended up as their Videoplasty DVD (woot!!).
if you have any questions on how long the drive is, use mapquest. you can do it in ~9 hours if you take highway 5. it's a long, straight boring ass drive through California's central valley, hundreds of miles of farmland (part of the reason we have the 5th largest economy in the world.) if you take the coast, it's more than a day, some sections are twisty and people don't drive fast in parts.
other threads I've written on the topic:
http://forum.ableton.com/viewtopic.php? ... =lands+end
http://forum.ableton.com/viewtopic.php?p=537232#p537232 <-- more about clubs and audio stuff to check out, like Audium.
http://www.audium.org/
hth, let me know if you'd like any more info. SF is a pretty small town, 7 miles x 7 miles.
And this week would have been the week to come down what with WMC and all. Especially since the star this year was Ableton Live.
