- You can start anywhere in the Castro, Mission (home of the burrito), or downtown. I'd recommend starting at Chow at Market & Church or The Pork Store on 16th at Valencia. If you wanted to go upscale on the weekend, Maverick at 17th and Mission is a fantastic brunch. Another option is to start in Chinatown (just north of Union Squre) for dim sum.
- From Castro take one of the N, J, etc. trains (every light rail train route in the city intersects at Church and Market) down to the Powell Street station. From the Mission you can take BART a couple of stops up to Powell Street.
- Once at Powell Street hop on the Powell Street trolley. A quintessential SF experience.
- Take the trolley up through the city where it will eventually stop at Lombard Street, which is known as the most crooked street in the world. Walk down the hill, take a few pictures and laugh at the tourists trying to drive down the damn thing.
- Once at the bottom of the hill, turn left. You'll be walking towards the water at this point. Within a few blocks you'll hit Ghirardelli Square. There are a ton of things to do here. There's a submarine museum, Fisherman's Wharf, chocolate, etc. Alcatraz tours also leave from this area (be sure to book your ticket in advance!).
- You have two choices to make from here: 1. Go left at the water over the hill to Fort Mason and wander through the shops and stuff there. 2. Go right at the water and hop on the F car, which is comprised of antique street cars from around the world. If you're lucky, and it's warm, there might be one of the open air ones trolling around.
- If you go with Option #1, you can keep on walking through the Marina (rich, upscale hood) to Crissey Field for some spectacular views of the Golden Gate bridge.
- If you go with Option #2, you'll go along the Embarcadero and eventually come to the SF Ferry Building. I'd get off here (where Embarcadero and Market meet) and wander through the marketplace at the ferry building. If you still have gas in the tank, you can take the BART a couple stops up to the New Montgomery station and walk down to Yerba Buena and the MOMA.
- Start anywhere you like in the city. Drive up and across the Golden Gate Bridge.
- Once across the bridge there's a turnoff immediately on the right for tour buses and people to take pictures. You could stop there, but that's where all the tourists are. Instead get off at the first exit and turn left to go up the Marina Headlands. You'll take that up to the very top where there's a turnabout and stunning, expansive views of the city and bay.
- After you're done snapping some shots of the city and the bay, get back onto the 101 North and head up to Muir Woods. It's about 15-20 minutes north of the city and is home to a grove of life affirming coastal redwoods.
- Once done contemplating those trees, head down to Fish at the marina in Sausalito. The ceviche and fish tacos will confirm what you already knew: Mexican food is delicious.
- From there tool back across the bridge and take the HWY 1 exit. This will take you directly through Golden Gate Park. If you've got time, stop by and check out the science center or museums.
- HWY 1 will cut out of the city pretty quickly. There are beaches and views OH MY about every mile or two. Pull off at your leisure.
- Eventually, about 2 hours later you'll drop into Santa Cruz. Make your way down to the boardwalk. There's all sorts of stuff to do down there: food, amusement park, etc.
- Once done there, take 17 through the mountains back to 280. The drive up 280 into the city is another wonderful drive.