If you're not confident on the bike solo then probably not a good idea to take a pillion just yet. Get used to the bike first spend a bit of time getting used to it and getting the confidence back before worrying about how to fire it round bends 2 up
On our rides we use a marker system so changes in direction are marked for the following riders, the reason we do this is because it allows the bikes to space out on the roads rather than riding as one large group, which is much safer, it also stops the problem of the slower riders riding outside their comfort zones trying to keep up, as no one gets left behind and everyone can ride their own ride.
A ride out is a fantasic way to boost your confidence on a bike, as you will be in the saddle for a day, the problem with short rides is it can take you 15 - 30 mins to relax into the ride, after that time you confidence increases much quicker, so if you only do short journeys you may find you struggle to get confidence quickly.
A ride out isn't a race, it's about getting there as safely as possible, along some nice roads, with good friends and a good day out.
