For our first chartering experience, we chose a Sunsail Flotilla in the BVI, one week. (2008) It was the perfect choice! BVI is easy, line-of-sight sailing, with short distances between stops, and the relative protection of the Sir Francis Drake Channel.
We were with our college-aged son, and loved meeting the other folks in the flotilla. We had Americans, Germans, English, Irish, as I recall. You could spend as much or as little time socializing with the others as you wanted. There were couples, families with younger children, and luckily for us, a couple families with other college-aged young adults in tow.
We found the Flotilla Captain, who was a local, to be helpful, knowledgeable and fun. The "hostess", a young English woman who was also a sailor, was really great at setting a "vacation" mood.
There were daily chart briefings with good advice and local knowledge on where we were sailing that day. We would then sail on our own, making our way to that night's rendezvous point. (generally, you have to be moored by 5 pm) You can then either eat on your own boat, or you can go and join the others at the restaurant for that night, which they have chosen, and which was usually the best choice in a given place.
We have lived overseas, so we loved the comraderie and meeting people from different places and cultures. Everyone is on vacation and in a good mood, so the evenings are a lot of fun. We did spend a couple of nights on our boat, just for some quiet time, and that was nice too.
Having the support of the leaders of the Flotilla was invaluable to us. It made us feel more confident as we sailed and navigated in a totally new environment, and took away most of the anxiety that a new charterer will normally feel.
Also, having the lead boat waiting for us as we reached a mooring field was helpful, because sometimes in the BVI there is a bit of a 'musical chairs' element.... being afraid you will be the one left without a chair (mooring)..we were not worried, because we knew that our leaders would help us figure it out if that happened, and it never did.
Since then, we have chartered again in the BVI (no flotilla) and in the Grenadines, Antigua and are headed to Sint Maarten this year. We highly recommend Sunsail Flotilla for your first time.