This is a good hike to knock out if you're short on time, live in the area and don't want to waste time driving. You still get great scenery, a bit of wildlife, moody weather, and more and yet you can launch just outside of Portola Valley. But on the flip-side you'll see a lot of people and hear some road noise once you near Skyline.
Last time I hiked Windy Hill it was pushing 90 degrees, sunny and calm as I scaled the totally exposed Spring Ridge Trail. I was hot and sweaty and wish I did the reverse loop. This time it was pushing 40 and windy and raining and I started by dropping down Razorback Ridge with frozen extremities. Learn from my mistakes. If it's warm, start up on Skyline and drop down the exposed Spring Ridge Trail. This way you'll huff and puff your way up the cooler, shaded Hamm's Gulch Trail. If it's cool, hike up Spring Ridge instead.
There are two Windy Hill parking spots on Skyline. For this particular hike I parked at the southernmost spot. Then I took Lost Trail > Razorback Ridge Trail > Eagle Trail > Hamms Gulch Trail back up to Skyline.
This is one of those great "workout" hikes. In fact, I ran across a lot of locals in running shoes either trail running or just hoofing it up to Skyline. The trails are in good shape. You can start this hike from the bottom off Alpine Road at Hamms Gulch Trail or from the top, like I did, at Skyline, down Razorback Ridge Trail. It's called Windy Hill for a reason. Pack layers. There are picnic benches and bathrooms located at the Skyline parking lot.