backpacking
1 day ago

I'd give this hike 2.5 stars, so I'm being generous rounding up to 3 stars.
I don't typically write reviews, but I felt indebted since I often use AllTrails, and I wished someone had told me what I'm about to write -- so hopefully what I write can serve as value for someone in the future.

We backpacked this trail in 2 days, spending 1 night at Jay Camp (near Big Basin HQ).
As most have commented, it's more popular to backpack over 3 days, and I didn't see any comments regarding 2 days, so that's my purpose for posting in detail.

Firstly, especially important for backpackers, unless you're getting dropped off, you can't start at Saratoga Gap, you'll need to start at Castle Rock (for parking a car) which will add additional mileage (~3 to 5, depending on which trails you take to meet up with Skyline-to-Sea).
We didn't know about the extra distance, and the popularly noted first day hike to Waterman Camp is only ~8 miles, which felt short for one day, hence our decision to try to squeeze the more popular Day 1 & Day 2 hikes into just one Day.
Also, a significant portion of this hike is along the side of the highway (though not directly on the highway, you can clearly see and hear the cars zooming by and you're often walking along side peoples private property and houses) which I find to be a huge drawback and is why I'm subtracting at least 1 stars from the rating. You can take some alternative trails, as we did, to minimize the portion along the side of the highway, but this adds more distance to the total hike and you'll still be spending a significant amount of time along the highway regardless.
All in all, it took us over 20 miles to backpack from Castle Rock to Jay Camp, which is a lot longer than the estimated 15 miles we had in mind, and this can be an extremely tolling addition, especially when carrying 50lb backpacks.
We also found that the trails weren't always clearly marked and the trail markers present were few and far between, so you're often unsure how much distance is remaining and you also can sometimes get confused and question if you're on the right trail. This fact is another reason why I'm subtracting a star.

In summary, I found the best part of the trip to be the first few miles starting in Castle Rock to the High Way (taking as many alternative routs to avoid getting to high way quickly) as well as the last part of the trip from Jay Camp / Big Basin HQ to the Waddell Beach.

If done again, I would simply do an out&back from from Waddell Beach to Jay Camp / Big Basin HQ OR an out&back from Castle Rock to Waterman Camp instead of doing the Skyline-to-Sea.
Other downside (which effects my rating) that I want to note are; from Castle Rock to Waterman Camp you hike near a gun club and hear a lot of gunfire which is disheartening when trying to enjoy the sounds of nature and, as other folks have noted and I feel honor bound to repeat, Big Basin HQ is very popular and crowded with tourist, so it can get loud and not as relaxing to camp and enjoy the sounds of nature.