San Jose to SF-Peninsula Route

Here’s one example (approx. 50 miles) of what we did a year ago in 5 days on the July 4th weekend:

1. San Jose arena hotel to Sunnyvale Maple Tree Inn (7/4, Wednesday)
2. Sunnyvale to Palo Alto, Sheraton (7/5 Thursday)
3. Palo Alto to San Carlos Country Inn (7/6 Friday)
4. San Carlos to Millbrae (7/7 Saturday)
5. Millbrae to San Francisco (7/8 Sunday)

This particular route is probably the easiest to start with. You will travel through some lovely established neighborhoods (Sunnyvale, Palo Alto, and San Mateo), some trendy neighborhood commercial districts (Burlingame, Redwood City and San Mateo), and lots of strip commercial businesses along El Camino. Once you get your bearings and pace, you’ll really enjoy the variety and flavor of urban walking. It’s not your nature walk but using the same basic skills as hiking–you will discover a different experience–lots of visual stimulation and a view to learning how people work and live in their daily activities.

Familiarize yourself with the landmarks, roads, and major changes. Make sure these segments feel comfortable and easily achievable, by visualizing the roads, sidewalks, and benchmarks. Feel free to modify or change any segments, and to find parallel streets to the main route that suit you. Keep in mind that parallel streets don’t always connect or follow the same route as the main one. They often twist, turn, or are truncated by dead-end streets, so your navigational skills will have to be ready.

You should also plan out each beginning and end point. You can always take public transportation to and from each point. The journeys are designed to pick these up easily from either end. Since the lowest and least varied elevations tend to be the same that major transit lines follow, this one parallels the BART and Caltrain routes. With some advance planning, you can opt out along the route if your plans change.

1. San Jose to Sunnyvale (7.5 miles, 2.5 hours)

The Arena Hotel is one of the closest accommodations to the San Jose Caltrain Station, so we selected this hotel for convenience. Since walking is normally a one-way trip, we start this journey in San Jose going northward to San Francisco. There are advantages and disadvantages with each direction, so you should decide which direction you want to walk in advance. For instance, after this route we found that it is easier to walk from San Francisco to San Jose as there is a downward trend in elevation from the City through the Peninsula.

The screen shots of each leg are provided for convenience and to give you an idea of what you should be downloading. Match these downloads and study them carefully for each segment. Make changes as needed.