First, as for surfing… Santa Cruz is the ultimate surf town. Not just surfing, but the whole lifestyle and vibe. Also, Ocean Beach in San Francisco is a world famous surfing spot… the rough and borderline treacherous tide that makes most swimmers stay away from it makes surfers flock to it… very long rolling waves that you can ride for a long time. However, North of SF, in Marin County, are more surfing meccas… Stinson Beach and basically all of Point Reyes National Seashore are really popular amongst surfers (albeit many in Point Reyes you have to hike down to, surf board in hand). My dad was a surfer, so I was dragged all around California and Hawaii and taught about key surfing spots.

As for Napa/Wine Country… honestly, if you’re only gonna go for the scenery, there are better places to go. Napa is great for wine tasting, and quite beautiful… but there are other spots in the area that are far more beautiful. Driving along Highway 1, especially North of the city (and South once you get near Monterey through Big Sur… but that’s kinda far) is absolutely gorgeous… driving along ledges looking over forested valleys, the ocean, occasional farmland, etc… a couple roads where on one side there’s a huge valley on one side and cliffs going down to the ocean on the other… deer, coyotes, etc… are common. And many small/quirky towns on the way (Bolinas, for example, is rad). Napa is far more developed, as it’s mostly worked land.

Architecture-wise, SF has some great architecture… many Victorians in Hayes Valley, parts of the Western Addition, The Haight (especially Lower Haight), and The Mission. Lots of Edwardians in Pacific Heights, The North Panhandle, the Tenderloin, and The Richmond.

Another great town is Petaluma. It was built before the 1906 Earthquake and is one of the few towns to completely survive it. It’s really cute/quirky… the downtown area, and various other parts of town, have great Victorian buildings… downtown built along the river in European fashion. It’s a fairly small town, but is really cool… actually, per square mile, it probably has a better/more interesting arts scene than San Francisco.

As for art… there’s some great graffiti art murals in the Mission District of San Francisco… some really gorgeous work. You can either take a tour or just do it yourself (if you do a web search, you’ll find some key locations). Also, throughout the city there are a few murals painted by Diego Rivera which are really great… one at the SF Art Institute, one at the City Club, and the others I forget. Also, SFMOMA is great (lots of Cornell, Magritte, etc…)… and right around it there are several small galleries, such as the Cartoon Art Museum which is wonderful (history of Cartoon and Comic Art from 18th Century satire strips to the first cartoons to early Disney movies to modern cartoons to modern political satire strips… including original cells from old Disney, etc… movies). Yerba Buena is more conceptual/experimental art, and can be really amazing or really boring depending on the exhibit they have going. Also, the Legion of Honor is absolutely amazing… mostly classic/classical fine art. Rembrandt, Degas, Seurat, Rodin, Reni, etc… As well as some token Greek, Egyptian, etc… art. And the entire place is slightly smaller but scale model of the Palais de la Legion d’Honneur in Paris.

Um… within SF city limits, great parks (forest, hiking, wildlife, etc…) include Lands End, Fort Funston, and the Presidio.

The Richmond neighborhood is great, and often overlooked by tourists… along Clement St from Arguello onward (the hub around 6th Ave) is very Asian, mostly Chinese, and is the local’s Chinatown. More non-Asian locals, but pretty much no tourists ever go there (so the shops themselves tend to be more authentic). And along Geary St, from Park Presidio onward (hub around 20th Ave) is very Eastern European/Russian… lots of cool markets, stores, etc… and a great Orthodox Cathedral. The Richmond is also, in general, the best place to find really good but really cheap food.

North Beach is also nice… the original Caffe Trieste, some great restaurants, and Peter & Paul Cathedral which has some amazing statues, and little maze-like side rooms with gorgeous shrines (note: most every church in SF is open to the public, and they’re used to people just checking out the art [statues, amazing architecture, paintings… a couple even have art from the Middle Ages and Renaissance eras in them] and don’t try to convert people… they generally won’t even acknowledge your presence except to smile and say hi).

Anyway, that’s too much. Everything mentioned (sans maybe Monterey/Big Sur) is a day trip at most from SF. Staying in the city, Days Inns are fairly cheap ($60 – 80 a night, even without specials). For something a bit more expensive but still not ultra-pricey, the Seal Rock Inn (right by Ocean Beach) is great… and their restaurant downstairs makes really good omelettes.

What a nice trip you are planning. My suggestions are: Stay away from Napa if you plan that visit for the weekend. It gets very busy. Try the Sonoma area (Dry Creek, Alexander Valley, Healdsburg), less crowded and beautiful:
http://www.wineroad.com/
For surf spots and a beautiful drive, head south on Route 1 (Hwy 1) aka: Coast Hwy from SF to Pacifica, NorCal surf
shop to rent a board and surf that beach or head further south on 1 to Santa Cruz.

First off you can go surfing just north of San Fran at Stinson beach or Doran beach or for tougher waves, go to Santa Cruz which is south of the city. In Napa you can tour a castle(called castello de amerosa), go wine tasting and car touring all for very little money. it’s also a great place to go on a picnic too. They have a nice Best Western in Calistoga where you can stay or in the city of Napa too. I would stay in San Fran for a few days, then head up to Napa for a few days. It takes about an hour from the city to Napa. They also have a cool museum in Yountville, St Helena and Calistoga. Get a AAA tour book and do your planning that way.

San Francisco is a beautifull city to visit, inside the city traffic is ok and it’s easy to get oriented. If you want to surf Ft. Point you can find cheap lodgging near downtown in Lombard Street (near Van Ness Ave.) there you can find decent motels and stay in between the downtown attractions (like Chinatown, Telegraph Hill, Fisherman’s Warf, North Beach-Little Italy) and the Golden Gate Park. Also you are in a good spot to drive northward to Sausalito, Muir Woods and beyond (if you want to go to Bodega Bay and surf Salmon Creek), in Muir Woods you can take a great family picture with a panoramic view of the Golden Gate bridge.

If you decide to surf south of SF, to Santa Cruz then you could spend the day at SF then go to Pacifica for cheap lodgging on a beach front (that way you can tell how the surf is) and from there you got a fast way out to the PCH and only 52 miles away to Santa Cruz.

I traveled once with my wife to SF in October and there was a Computer convention going on, almost every Hotel was booked out, but we found lodgging in both these places (and cheap).

Try out the Clam Showder on a Sourdough bread at Fisherman’s Warf and if you go to the zoo, be carefull with the seagulls, one distracted my wife appearing right in front of her in mid air while another took away a Hot Dog from her extended arm even thought there was a sign warning you about it at the cashier’s desk.

Hands down go to Santa Cruz.
He can surf a short stroll from the Santa Cruz Beach and Boardwalk. You can take the kids to ride some kiddies rides and wander some shops while he hits the waves. Bring a picnic lunch and meet up on the beach. I’d suggest just north of the wharf. Less noise and people than the Boardwalk side so you’ll be easier to find. It is also close enough to the surf that he can carry the board.