...when the boat is on the roof? Do you intend to keep the kayak on the roof at all times except when paddling, and if so, would it keep you from using the hatchback for loading or unloading other items?
We need more information from you.
In your experience, do you prefer one over the other? And why? What would make you consider another option?
Do you have storage space for a trailer?
Do you have physical limitations (height, injuries, etc.) that favor trailering?
The trailer wheel bearings are easy to deal with: Just keep them lubed (not overlubed) with a grease gun; it only takes a minute to do.
I have a trailer as well as a roof rack. The trailer gets used to haul the kayak(s) almost every time. Even if it's only one kayak, because if there's only one kayak that means it's only me to load and unload it, which makes trailering the better choice. My husband hates rooftopping as much as I do, so even when we both go paddling, we use the trailer.
The only time I rooftopped on a solo trip was when I knew I would not be stopping to paddle on the way out or back. It allowed a bigger choice of motels on the route, since the ones that are in towns sometimes don't have much parking. The ones in rural areas or along Interstates usually have enough space for trailers.
URCHIN Portable Anchor
Wabakimi Canoe Pack
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