Larger group then a sat nav file and someone leading the drop-off-system who's ridden the roads before. Preferably with a TEC who knows the roads too. Drop-off-system allows for fluid riding and done correctly accommodates a mixture of riding abilities and wants without stressing the slower riders to keep up. A few mates that ride together, it's a different matter. Just get out there and ride looking out for the man behind you. Just going where your nose takes you, won't that eventually result in a few dead ends and some piss taking in the pub that evening?