We just went this past June for 2 weeks. This was our second trip to the BVIs. First time was with Moorings out of tortola and everything was excellent but pricey. As a first timer to that area, we did a flotilla which is not a bad idea for your first time there. We had a lead boat from moorings that gave us daily captain meetings of where we needed to be by 3 or 4 pm and also assisted with dinner reservations, points of interest, what to look out for, weather briefs, mechancial help, beach parties and most importantly the exact path into Anagada. back than, you had to follow a company boat, you weren't allowed to take a charter into there without one.
For the second trip this last year, price was a big consideration because it was 8 of us. We rented a 47 foot mono-hull (figuring if we got the wives and teenagers on a cat they would never go back to our own monohulls). It was plenty of room (4 cabins and 3 heads). We did a combination BVIs and USVIs. This time Sunsail out of tortola had the better price. We provisioned thru Bobbys. The boat was more beat up than the moorings boat and the ectronics were pretty poor to say the least - but she did sail well. They are now owned by the same company and all three (moorings, sunsail and footloose) share the same base. Morrings is top line, sunsail middle and Footloose bottom and price goes accordingly. The difference is the age of the boat and equipment.
As for Bobby, we were a little disappointed; price was great compared to what the base offered. Our entire bill from them including sodas, beer, wine and the hard stuff was about 25% lower than what the base wanted just for food. Our issue was they kept loosing our order that day. We were told that it would be there before we arrived, than by 2, than by 4, etc. It did finally arrive around 10 at night. We chalked it up to "island time mon".
Anagada is defintely worth seeing. But to be honest, some of the best anchorages we stayed at this time were on the back of St Johns and St James islands. Few boats, hardly any other charter boats, very very clean water, excellent beaches and snorkling and just very peaceful. The problem is that once you cross over to the US side, the charter company can not come to assist if you have a problem. You will need to sail back to the british side to get mechanical assistance. Not a big deal but worth mentioning. You'll be amazed at how close the islands are. You should check out and checkin with Customs/Immigrations but that is pretty painless and not too expensive.
We did not want nor feel the need for a generator and AC. The temps got warm but there was almost always a breeze and the breeze boosters and fans really help. We have learned to bring 12 volt or batterary operated portable fans. Actually, the kids that were in the forward cabins complained it was too cold at night. Can't say the same about the aft cabins. The fans are key there. What we did need was a water maker!!! We had four tanks and could only make it about 5-6 days on all of the tanks. Having four teenager girls demand tons of water and getting 1 tank filled in Soper's hole took almost 2 hours because the water pressure was so poor.
Lastly, we did layout a daily plan and pretty much stuck to it. We covered the anchorages we wanted and had a great time. If you do a flotilla, they will take you to the popular spots.