Valve size is the least of the issues you are about to uncover. Yes, valve to bore clearance is an issue, and you can only bore a Windsor .030 for more clearance, which is not enough for anything. the best way is lay the exact head you are going to use on the actual block, and check. The next problem is the 351 heads had a larger diameter head bolt, and you must get the head bolt conversion kit, or drill and tap your block for the larger bolts. It was once available from Ford, but I'm sure that is long past. An aftermarket source is available I'm sure. The next issue is combustion chamber volume. There are dozens (maybe more) chamber volumes on Windsor engines. This can make a swap impossible even with special pistons. The next problem is there have been several methods of guiding the rocker arms over the years. Early versions used pushrod guided rocker arms, the next version used the rail type guide on the valve stem tips, requiring longer valves, and several other changes. The next version used a positive stop type, the next version used the pedestal type, which is the GT-40 type. The early hi-po engines commonly were converted to pushrod guide plates, and hardened pushrods. All of these swaps, if you can persevere, will need a complete valve train reconfiguration.
After all of this, I have to ask, why? My sons and I go to the road races very often, and even heavily modified 260 Tigers can't keep up with the 4 cyl foreign cars, they just don't have enough power. Even a very heavily modified 260 just doesn't cut it. Just use a 289, and with a QUALIFIED Ford engine builder doing the work, (read, not a backyard hack job utilizing Jegs parts) 500 hp and 9K plus rpm can reliably be obtained, and you will over power most chassis out there.