People in San Francisco don't often consider San Jose a worthy stop. Many float through for Vietnamese food or cheaper gas than in the City, then continue on to the Gilroy outlets, Santa Cruz, the Central Coast or LA. But I'll tell you a secret, San Jose is worth your time.
In and around Cesar Chavez Square you'll find enough to keep you busy for days. Cesar Chavez Square, erected in the 1880s, is a central hang out spot for locals and tourists. Here you'll find everyone from dreadlocked hippies banging drums to women in saris to kids running through the fountains. It is the ideal spot for a picnic or watching the planes land in the airport close by.
What to do: Start with the Tech Museum. With the price of admission, you get to view an IMAX film. The museum itself offers so much information about how the world works, you'll want to spend hours playing with the interactive exhibits.
Around the corner, kids will love the Children's Discovery Museum. WIth everything from live music to bubble machines, crawl space for little ones to interactive science and art rooms, this is the kind of spot that mom and dad can chill out while little Logan runs all over the joint, tiring himself out.
The San Jose Museum of Art often has some of the most innovative exhibits in the Bay Area. Modern art lovers will want to spend some time exploring the collection and rotating display of art.
Also of note are the various art, music, movie and farm festivals that take place nearly every evening around the square (see my Northern California: An Explorer's Guide for more details).
Where to eat: When you get hungry, you have a few great options, but my current favorite is Michael Mina's Arcadia steakhouse. Spacious and hip, sit at the foot of the Marriott and watch the chefs prepare your meal in the wood oven. This is where you will find the best the lobster corn dogs in the state. Don't pass up your chance for a steak or cioppino either. The sides though are what put the restaurant over the top. Wood fired exotic mushrooms, truffled mac and cheese, whipped potatoes...just thinking about them makes me want to get in the car and go grub. It is pricy (a dinner for two with drinks ran us $160), so plan accordingly.
San Jose is also home to the best coffee shop in the South Bay--Barefoot Coffee Roasters. Disregard the location in a strip mall and order a latte, then sit on mismatched chairs and relish in the fact that your coffee could win a barista latte art contest.
Where to stay: If you don't want to drive home, the De Anza Hotel, Hotel Montgomery or Marriott are within walking distance from the square. All balance hip amenities with retro appeal. The bummer is that parking rates are steep. For deals, go on weekends.