Flights
Both SFO and SJC are equidistant from Palo Alto and are great options to fly in to. There is no issue getting an Uber or a Lyft from either. Oakland is a bit further, but not prohibitively far.
Hotel or Air BnB?
Hotels along the entire peninsula get really pricey really fast. We recommend looking at Air BnB - it can be slightly cheaper and there are more exciting accommodations. We’d also recommend looking at the Marriott Residence Inn..
Ground transport
Between parking, gas, and fees, it probably works out even if you choose to rent a car or use Uber/ Lyft. Although Caltrain and Bart service long distances up and down the peninsula, we don’t recommend relying on them because the timing is inconvenient and the stations are somewhat inconveniently located.
Fun things to do in San Francisco
In San Francisco proper, check out Twin Peaks, Ocean Beach, Lands End, Golden Gate Park, and the 16th street tiled steps. And Trouble coffee, which was featured on This American Life, and in our opinion the best burrito in SF (skip La Taqueria, which was 538’s pick. It’s OK, but not great).
Fun things to do in the South Bay
University Ave in Palo Alto and Castro Street in Mountain View have tons of restaurants and bars. Sancho’s Tacos is among our favorite, there’s one in downtown PA and one by our house in mid-town. And Tacos El Grullense in Redwood City.
The Dish is a popular 4 mile hilly hike right behind the Stanford Campus. Arastradero, and Fremont are our favorite hikes, but check out all of the Open Space Preserves.
If you have a few extra days
Check out Davenport, which is ~30 min north of Santa Cruz. It’s a cute town with a beach that has an abandoned pier and some coves with cool rock formations. Up north, Healdsburg and all the wineries in Sonoma are also gorgeous