Hi...I'm going to be taking a walking holiday in England as well, the length of Hadrian's Wall, about 84 miles, not quite as adventurous as your trip but I'll be turning 60 and hiking by myself, so this will be adventure enough for me. If you have never hiked before, I agree with others, that the Pennine Way may be a bit much. Start practicing now. I'm using a tour company to schlep my luggage, too. They provide a list of equipment they believe is necessary and equipment which would be nice to have. I bet your tour company does as well. And they will most likely give you advice on all manner of things if you ask. I would trust their judgement since they are probably located near the area you'll be hiking and most of them are also hikers. Have a great trip. Tuli