My family has been living in Santa Cruz for almost 40 years. So when my uncle says Pleasure Point was as big as he has ever seen it, you know it's been big.

NY/NJ to San Jose or San Francisco usually runs $350 plus, so this one gets you there at 40% off (maybe more!). What's even more nuts is that a lot of the best trips dates are direct / non-stop.

If you do end up going, respect the locals, and definitely keep it on the DL where you heard about this deal. Don't want to get roughed up too bad next time I'm out there.


Last time I flew in, stepped off the plane and drove over the hill, just as a big swell was tailing off. Everyone had been frothing so hard for a week straight that when I paddled out there were literally 3 people at first peak PleasurePoint in perfect 6 foot.

Fucking unreal.

That one is pretty much how I remember it (and shot in 30 minutes to give you an idea of the rippers that surf it ever day).

Odds are you aren't going to see it like that, but going during swell season certainly increases your chances. As does having a friend who knows the other more remote breaks that are damn near as good when the point is too packed to surf (just leave your car unlocked and don't keep anything fancy with you if you venture out to surf them).


Obviously some iconic Skate stuff has come out of not only the Santa Cruz Skateboards brand, but the city of Santa Cruz over the years. But as you can see above, there is also a ton of fun being had pretty much every day on four wheels.

I think part of that is the attitude, part of it surf culture woven throughout, and part of it is access to some insane parks (built by the town... and otherwise)

Downhill / Longboard

When the Caliber guys have access to spots like this via car / tent/ sleeping bag:

And they still choose to put their home office in Santa Cruz, that lets you know just how rad the town is. Which should tell you it's good enough for you to visit and ride at least once per year.

Last time I ran into those dudes they were making the wise decision to hit up Happy Hour at the Crow's Nest Restaurant right on the Harbor. If you know what's good for you you will do the same, in-between sessions, while you are in town.

Here's Chubbs not so far from home:

As mentioned: have fun, make friends and respect the locals... also stay in your god damn lane.

How to Book

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