3 Impressive Skatetrips You Should Be Following

3 Impressive Skatetrips You Should Be Following

Through social media we’ve become aware of some impressive skateboarding trips that we think epitomizes the term “challenge.” As an organization we feel it’s our responsibility to help generate awareness to these efforts in a non-bias manner regardless of the equipment they ride or journey they choose. Each of these projects have a charity component if you feel compelled to support. 

We hope to launch a formal grant program for skate projects in the future, but in the meantime we have sent a small contribution to each of these projects on behalf of the IDSA funded by an anonymous donor (not membership dues.) Without further ado, here are 3 skate trips you should be following:

1. Jayo Skates Cuba 


Jayo is likely the first person to ever ride a Pantheon across Cuba. He has also previously skated across New Zealand. We’ve been in touch with him and he plans to participate in the May “Warm Up” Challenge. Overall, we get great vibes from his frequent updates on Instagram as he skates and mingles with the local people.



Below is a excerpt from his website:

Jayo is a cross-country long-distance skater. In the months of April and May, he will raise money for Cuba Skate by skating across the entire island of Cuba from West to East - with just a longboard and a backpack! During his skate he will be visiting Cuba Skate in Havana, the provinces, and at the recycling center in Matanzas - where plastic from Cuba’s Skate’s cleanups is repurposed into skate-able objects. 

“I want to show you all first-hand the incredible groundwork Cuba Skate is doing for youth communities and their innovative work in sustainability.  Further, I want to showcase the beauty and culture across Cuba.”

Follow Jayo’s Cuba Skate fundraising journey on Instagram @jayoskatesworld for "skate-packing" adventure content in Cuba, or at www.jayoskatesworld.org

Please donate to support this project, Cuban youth, and sustainability in Cuba!

Donations support:

  • Skate Classes
  • Woodworking Cooperative
  • Sustainability and Ocean Cleanups
  • Youth Development
  • DIY Skatepark Builds


2. The Push - A Skateboarding Relay across America

In June of 2023, a four person team made up of longstanding IDSA community members: Paul Kent, Miles Kipper, Andrew Andras and Rick Stubblefield will attempt to set the Fast Known Time for a skateboarding relay across America. This trip will be supported by Jack Smith and his son Dylan who have both completed previous cross-country trips most recently in 2003. Their route will take them from the Washington DC area to Oregon.

As of now, details are still forthcoming and we’ve yet to receive a link to help support them or follow along. We will update as necessary. 


3. Chad Caruso - Skate Across America 


As we write this, Chad is somewhere in the middle of America grinding along on a regular skateboard rolling on Seismic wheels. His frequent YouTube updates are filled with candid commentary and musings as he cranks out mileage. On Instagram, his posts are filled with ride data and fun stuff he sees along the way. His route started at Venice Beach’s iconic skatepark and will finish in Virginia.

The following was taken from Chad’s gofundme page:

Hey everyone, my name is Chad Caruso and I’m a skateboarder from Long Island, New York, and on March 24th, 2023 I will begin skateboarding 3,000+ miles across America to raise money for addiction awareness. 

I have been sober for six years now and doing so has completely changed my life for the better. I wouldn’t have been able to attempt this skate across the country without the energy and focus that sobriety has given me. The goal of this fundraiser is to highlight the importance of having something passionate in your life to focus on. 

25% of the money raised will be donated to Natural High, a drug prevention nonprofit that inspires and empowers youth to find their natural high and develop the skills and courage to live life well. The rest of the funds will be used to cover food, hotels, and other expenses throughout this two month long trip. 

Thank you for being a part of this! It means more to me than you could ever know.


Bonus: Ryan Swain’s World Record Attempt

While technically not a “skate trip” per se, here’s another project you should be aware of. On May 8, a UK skater Ryan Swain will be attempting to break the Guiness World Record for longest distance traveled on a skateboard on a regular board. He is riding for a number of causes including a mental health charity called Mind which we contributed to. Learn more here.

While we all know Joe Mazzone holds the World Record at 313.9 miles in 24 hours, the GWR is still held by Andrew Andras @ 261.8 due to massive administrative challenges dealing with Guinness. We wish Ryan luck.


 Planning an epic skate trip or project we should know about? Drop us a line.


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