From Redwood City to Coyote Point, you'll see many cool sites along the peninsula. Bair Island, Foster City Beach, San Mateo Bridge, and Coyote Point Recreation Area. The view is fantastic and you can often get good downwinders here in the summer with the west wind. In the winter, the south wind can be great too.
On January 7th, 2017, I organized the Mike's Paddle Team Focus race team to paddle this stretch. The winter storms were coming with what the meteorologists call an atmospheric river event - there's apparently a large volume of water down south and streaming tons of rain to northern California. In the next several days, there were severe wind and flood advisories and Tahoe got 10 feet of snow. But with winter storms, the wind typically come from the south and we were in luck for a fun downwinder from Redwood City to Coyote Point which we finished in about 3 hours. The only problem was fighting the wind to get out of the Redwood City channel. There were few wind shadow spots and some of us got stuck in the shallows on the north end of the channel. It was a short carry to get around the point but once we were going north it was super fun.
Conditions: 15-20 knot S/SW wind, mid-50's, high tide and ebb tide about 1 knot.
Hazards: The low tide is typically the issue here. Wind was also so strong that some of our folks either turned back or had to carry the boards around the point. In the summer you'll have the same issue with the west wind where it would push you to the south end of the redwood city channel. San Mateo Bridge can be intimidating to beginner/intermediate paddlers with strong current or wind, the waves tend to get bigger around the bridge. Boat traffic in and out of marianas are generally sparce but be aware of blindspots.
Put-in: Redwood City has multiple marinas, but some of them are private and will absolutely refuse small boaters to put-in and take out. The public ramp situated next to the Stanford Sailing and Rowing Center is the quickest access to the water. I find that the south end of the center with the small boats is best for SUPs (see below picture).
Take-out: Coyote Point Beach is a perfect take-out for various small boats. There's Boardsports California which rents and sell both wind/kitesurf boards and SUPs. Be aware of GPS confusion, there's a Coyote Hills park in Fremont. Some of our shuttle drivers were reporting that google maps were leading them there instead. Inside of the Coyote Point Recreation Area, there are two parts also - the marina and the beach. Make sure you direct your driver to the beach.