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The trails are marked. It is always better to get a map and plan your trip. Hikers can join the trail at many points along the 30 miles of trails from the 3,214 foot elevation at Castle Rock to sea level at Waddell Beach, but the Skyline to the Sea trail officially begins at Saratoga Gap. Hikers often start at Big Basin Redwoods State Park. The Redwood Trail, across the parking lot from Big Basin headquarters, meets the Skyline to the Sea Trail. Going to the sea from this point in Big Basin can be a hike of about 14.5 miles. A few detours can lead to several campsites, waterfalls and points of interest (Like the gift shop at Big Basin!). Campsites require reservations. Hikers can take the Santa Cruz morning bus up to Big Basin, hike to Waddell Beach and catch the late afternoon bus from Waddell Creek to Santa Cruz. That still leaves getting to and from the Santa Cruz Metro Center. There is no cell phone service at Waddell Creek. Just start heading south. Cell phones should get a signal at the ridge above Scott Creek.
History The trail was built in segments starting in 1969. As it grew, it incorporated already existing trails, with deliberate efforts to include junctions to other trails. At first it was spelled with hyphens, Skyline-To-The-Sea-Trail.
Businesses There is a gift store at Big Basin Redwoods State Park as well as at Rancho Del Oso State Park (Seasonal hours).
Transportation 
The bus shelter at Waddell Beach Santa Cruz Metro Transit has two visits a day to Big Basin and two visits a day to Waddell Beach. The schedule also runs on weekends, most of the year. Check with the Santa Cruz Metro for details and times.
Maps The Santa Cruz Mountains Trail Map Set includes the Skyline to Sea trails. It can be bought from Mountain Parks Foundation online at http://www.mountainparks.org/store/ or at the gift shop at Henry Cowell Redwoods State Park (The gift shop at Big Basin has seasonal hours). 
At Big Basin, Skyline to the Sea trail in red. Click to enlarge.
Video A documentary video of the Skyline to Sea trail starting at Castle Rock and ending 32 miles later at Waddell Beach. A seven minute adventure http://walkifornia.blogspot.com/2012/01/skyline-to-sea-trail-castle-rock-big.html
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