Good weather, few to no other people aside from friends, ending the ride with some good food or something is always quite nice. Also doing it aboard a nice bike helps but all my bikes in different ways are quite nice so that is never an issues.

In terms of tires, wider, more supple tires will give you a better ride. It is just the facts from the data people have gathered in more recent years. Heavy stock tires that are probably more puncture resistant and possibly narrower than the bike can actually fit will give you a less than optimal ride. The wheels can make a difference but mainly the tires will make the biggest difference. Look for something like an Open Tubular it is built like tubular tire but instead of being sewn around a tube a bead is built in just like a clincher and it is suitable for standard clincher rims and tubes. They are not as puncture protectant as heavier tires designed around that but keeping proper pressure and running a wider tire and doing your best to avoid potholes and piles of glass and such will help limit punctures. They are going to be more expensive tires but they can transform the ride. A wider tire is always better but a wider more supple tire will really make a huge difference.