Assuming no major traffic (big assumption) and not accounting for breaks...

SD to Santa Monica should take about 2.5 hours.

Santa Monica to Oxnard/Ventura on CA-1 should take 1 - 1.5 hours.

The rest of the trip up 101 to Pismo Beach should take 2 - 2.5 hours.

Total trip should be 5.5 to 6.5 hours.

I have not driven the coastal route for about three years so hopefully my information is not outdated but if it is I'm sure somebody will speak up.

Lots of wineries around the Santa Barbara area. I cannot recall any specific ones but if you do a internet search you should find some.

laurenzo, we're pretty flexible! As this will be our longest driving day, and I'll have two getting-cranky teenage boys, something laid back, seafood (of course!), relax with a glass of wine...

one of my favorites is Steamers in Pismo. There are beautiful ocean views, a great menu, and of course, a great wine list. My favoirte is the salmon w/ mango salsa. Have you heard of McClintocks? It is in Pismo also and a fun place to eat. Your boys would like it. It is primarily a steak house but they have fish selections too. My teenagers like to eat there. Both restaurants are pricier than some, but the food is great. They give large portions at McClintocks so you could even share a dinner. They are famous for their beans. The waiters will refill your water glass blindfolded while standing on a chair :) For more casual dining, you can eat at Splash Cafe or Brads, although I am not sure they have wine. Both places are known for their excellent clam chowder. There is also Scotty's, which has outstanding fish tacos. Enjoy!

Any other tidbits of wisdom out there? Other than the zoo and Balboa Park, any must sees in San Diego? (We've been to Sea World in Fla many times, so that's not on the list). Wineries in the Santa Barbara/Santa Maria area? Great places to eat...more on the casual side, but how do they say..."elegantly casual"? Things to do with teens at Half Moon Bay (while DH golfs)? Once again, many many thanks!

San Diego is the perfect place to relax on the beach. I never really spent much time on the Coronado beaches so I can't speak to them but a bit north the beaches of La Jolla Shores and Torrey Pines are fantastic and family friendly.

Torrey Pines State Park has some wonderful short hikes that take you over the bluffs to view the ocean (all are less than a mile or so).

Visit the La Jolla cove for an evening of shopping, dining, and taking in some great views. One of my favorite restaurants is "The Spot" on Prospect Street in La Jolla. I always go back when I'm in SD. It is 'elegantly casual' and the food is always great.

Wineries?

In Santa Barbara city, there is Santa Barbara Winery - friendly taasting room and with good Pinot Noir.

Santa Maria - Byron Winery and Foxen Vineyards.

Santa Ynez - For some good QPR syrahs, go to Bridlewood Vineyards and Gainey Vineyards.

Enjoy.

Julia Pfeiffer Burns State Park: One more quick question. I'm confused (easily done!) about excatly where this park is...it's the one thing we didn't get to see on our last trip a couple of years ago and I don't want to miss it this time! As we're driving North from Hearst Castle, is it before or after Nepenthe?

I found this map, and website, helpful on our recent trip up Highway 1. It shows clearly where everything is.

http://www.bigsurcalifornia.org/map.html