Hello
I am afraid you have several potential problems.
Firstly the weather. Flying in the winter on a specific day in a light aircraft is at best unpredictable. It might be possible, it might be possible in a de-iced airways twin, or it might even then not be possible at all!
Next, the pilot. You can only cost share with a PPL (that is the law). So at best he would be paying for half of the trip. In order for you to pay for the whole trip you would need a commercial pilot and the trip would be air taxi work all adding considerably to the cost.
Thirdly, the cost. So taking one and two and the fact you might not want to cross 80 miles of sea on one engine, it will prove expensive - but maybe you had already taken that in to account.
On the plus side there are plenty of air taxi operators and schools who could get you to Le Mans and back in most conditions. If you need some ideas PM me and I am happy to help.