For those interested in bareboating, the BVI's are certainly the place to go for easy. One might call them the Kindergarten of bareboat sailing.
A step up (in difficulty) and backward (in time), the Grenadines are certainly a great destination. Longer sails, but still in the shelter of islands to windward, for the most part, make the Grenadines a good second step. Communication isn't as good as in the BVI (oh horrors, no internet), and the mooring buoys may not be as reliable necessitating more anchoring, but there are certainly fewer crowds and plenty of large, comfortable anchorages. Thankfully, there are 'boat boys', viewed as pests by some, who we find to be extremely helpful to strangers and regulars alike, by offering anything from good advice on where to anchor, help onto a mooring, and fresh homemade (and absolutely fantastic) banana bread. See Buda in Clifton, his sister bakes the best, though all are really good. These boat boys also offer fresh fish and lobster, if your luck trolling wasn't good that day, or in some places, a wonderful lobster meal ashore with lots of excellent local sides. A real taste of West Indian cooking, the term cuisine being a little pretentious for this food. Should you not wish to avail yourself of their services, a simple, "No, thank you." should suffice. No need to be rude, these gentlemen and one lady, Dede in Bequia, are only trying to earn a living.
From the Grenadines, it can be a pretty big step up, depending on the weather, to sail the northern Windwards and eastern Leewards. Much longer open water sails between islands and more densely visited islands (by yachts and shoreside tourists and their day trip boats). Up here the boat boys can be a tad more aggressive, but again a simple, "No thank you" perhaps several times, should suffice.
A good day ashore could include a little 'bus roulette'. Go to the main bus station, close your eyes and pick a bus. For sure it will eventually return to the very same bus station, as would any other that runs the same route, should you find a place where you want to get off and check things out. Though a wonderful way to meet the locals and a great day of adventuring, it is by no means the same as a guided tour, which, when done with a good guide, is a much more in-depth view of an island. We played bus roulette for several years before we took a tour of Grenada with Cutty, and we'd drivin by so many interesting things and places without any idea. Most especially the Monkees that come out of the trees to meet any visitors that stop there.
There are many wonderful places on this big blue marble to charter, but for me, the eastern Caribbean is my preference. Whereas most 'tropical paradises' are in island chains that go east to west (the Fla Keys, all the SoPac island groups and Hawaii): directly downwind or up, in the West Indies the winds are generally from the east and one is either sailing north or south.
So, don't get stuck in the BVI, there are plenty of other places that are just as much fun to sail, many with a lot more to offer.