We did a Sunsail Flotilla in the BVI last year at this time. I think it provides a great transition from captained to going it on your own. As mentioned above, they are not designed to be follow-the leader type sails. You are very much the captain of your own boat.
However, they provide daily briefings and most important to us help very near by. For example a problem with our dinghy engine was solved on the spot by the flotilla leader instead of us having to wait several hours for a mechanic from the base. They generally meet at a pre-determined time each evening to brief on the next day and give the anchorage for the night. If you miss it, no problem, call them on VHF and they will come to your boat and give it to you in person. You are on your own during the day to make the next passage. In fact we left our flotilla for 2 days to join another group for the run to Anegada. All seems to be acceptable as long as the flotilla leader knows where you are.
We found the recommended anchorages to be a good mix. The other boats in the flotilla provided instant friendships (much like the group seating on cruise ships to us). They are not limited to lesser experienced sailors either. One of the other boats in our flotilla had 80+ years of sailing experience on board split amongst 4 individuals. One of the couples had met when they where a flotilla captain and social hostess many years before. On our 1-week they had group dinner (optional) planned for about 3 nights.
In summary, I think the small supplemental of a flotilla is more than worth the extra attention and peace of mind.
S/V Anything Goes
1987 Pearson 31-2