I insist that you ride a skateboard with some kind of dropped deck. The lower platform saves your knees from bending as much to kick and brake, which multiplied over the distance reduces a lot of wear and tear on your legs. For my ECG trip and some day trips, I rode a Globe Geminon 41” board on Paris 180mm 50° RKP trucks and Orangatang Durian 75mm 86a wheels. This not only served me well, it survived being run over by a pickup truck with minor cosmetic damage. My chief complaint was that it was really large and heavy – good when riding it, bad when needing to carry or travel with it.
Now I ride a Pantheon Pranayama (2020 model), a board purpose-built for distance riding and carry or travel. It has the same dropped deck and giant Orangatang Caguama 85mm 77a wheels, in a package slightly smaller than a street board. Paris 149mm TKP trucks definitely contribute to that. A set of practically invisible shock pads smooth out the ride and reduce the rattling noise of truck metal on deck wood. I can’t say enough good things about this board; read this detailed review for an extended take.
I briefly tried a Subsonic Century 36” and have only heard good things about the Longboard Larry Pusher, if you want other deck options. Or you could even try the pumping technique, and get a board more suited for that. Finally, I’ve only used Bones Reds bearings the entirety of my skateboarding life and never wanted anything else.
The caveat here is all my trips have happened during the summer, in especially hot (and often humid) areas. The MSR Hubba NX ultralight single-person tent is fantastic. It’s very light, quick to set up, and quick to pack away. On the ECG trip, I slept on an REI Stratus sleeping pad and in a Cocoon CoolMax Travel Sheet. I’ve since downsized the sleeping pad to the Flextailgear Zero, which is like a quarter of the packed size and still good enough; and swapped the travel sheet for the Gravel Layover blanket, which packs to the same size and is much warmer. A tiny inflatable pillow is worth the pack space, in my opinion.
I can get obsessive about backpacks. I want something more like a casual daypack, and none of the additional hardware or baggage that comes with a proper framed backpacking pack. For my main trip, the Keen Newport DP II served admirably. Everything except the tent fit inside the pack itself, and I could wedge the tent into its outer webbing. On the negative side, its zipper hardware eventually corroded and some straps frayed away. Now I have a Dakine Wndr 25L which is rated at the same capacity despite a more streamlined appearance.
For day trips or anything out-and-back, I obviously don’t need (nor want) a full-sized pack with all my camping gear. I initially tried a Platypus Tokul XC, which could hold a 3L water bladder as well as snacks, my wallet, keys, phone and earbuds, and a skate tool. I’ve since switched to the Nike Hip Pack, a giant fanny pack worn like a crossbody sling. It has enough capacity for the same stuff and a soft water bottle. And it much better fits the aesthetic of someone out for only a couple miles.
As far as basic outer clothing goes, a nice wicking t-shirt and shorts will do. I was fine with two of each and four pairs of underwear. Make sure the shorts have pockets! Mine did not and I had to use the pockets in my raincoat for all post-travel casual walking around.
Traditional skate shoe details like reinforced toes and gummy soles are for executing tricks, not pushing long distance. Ultimately, any running shoe will work, as long as it’s breathable and its soles can stand up to foot braking. Heavy-duty Keen Newport H2 sandals were a strange recommendation that paid off in spades. My feet were never hot or sweaty, and comfortable for almost the whole time. While the soles held out from North Carolina to Key West, they went straight into the garbage at the end. I did get a couple blisters from where the straps rubbed against my feet, but I would still choose these all over again.
Wear a helmet. I swapped the Triple 8 Sweatsaver for the Bern Allston in an attempt for more ventilation, but the reality is I will always be sweaty. Now I’m eager to try out the Park & Diamond collapsible helmet which will be ideal for traveling.
Whatever iPhone is recent enough is pretty much my everything device: taking photos, listening to podcasts, tracking progress, writing and publishing daily recaps, even reading ebooks at night. I plan routes and link to them later via MapMyFitness, and I have written recaps in Day One and Medium, though now I capture thoughts in the Notes app and write them up later here.
Shout out to Castro, one of my favorite overall apps, for keeping me entertained when it’s safe to listen. And to that point, I find the pack-in EarPods to be perfect: they don’t block out road noise, I certainly don’t worry about wrecking them, and the sound quality is more than adequate for spoken word.
Definitely pack a first aid kit with bandages, alcohol wipes, Neosporin and Cortisone, and plenty of Ibuprofen. Sector 9’s carabiner skate tool is amazingly light while still useful in a pinch, if you can find it in stock anywhere. Paris’ skate tool is much heavier, but much sturdier, and packs down small. The TravelCard phone charger is perfectly suited for day trips, but bring your actual wall charger for anything longer.