I went on the Club drive around the Isle of Wight a while ago, and it was a really nice format.
There were about 6 runs of 15-20 miles each, with a rendezvous between each (usually in a scenic car-park) one where we could gather together for chat, photos and ice-cream. With a lunch stop in the middle.
Also with a great briefing, eg:
23.
11.55am to 12.20pm: The second stop is at the St Catherine’s Hill car park. This car park is free (which allows us to overlook its slightly poor surface). It is well worth taking a short walk from the car park to the headland beyond (signed as part of the coastal walk and Footpath C35 to the ‘Cliff Top Viewpoint’). It does what it says on the tin (but do keep your distance from the cliff edges). There are sweeping views back across West Wight (including to the Needles if it is not too hazy), down to Blackgang Chine, and up to the 14th century St Catherine’s lighthouse (the ‘pepperpot’). Unless you are really early (and very fit) there will probably not be enough time to climb up to the lighthouse. The views from the headland are not that different. There are no WCs at the car park but there is sometimes a van selling hot drinks and ice creams, and some newly installed wooden seating.