Re: Abacos or BVI
The BVI are the classic bareboat charter grounds, but if you want uncrowded anchorages and don't care that much for the beach bar scene, you might consider chartering out of Red Hook on St. Thomas, USVI. You could explore the north side of St. John (Leinster Bay is one of our favorite stops) and the south side is even more secluded (Salt Pond Bay, Lameshur Bays). Your activities would be the beaches and you could take short hikes. You'd be mostly on your own for meals, however. You could pick up a mooring in Caneel Bay and dinghy into bustling Cruz Bay if you want restaurants. You could do a leisurely circumnavigation of St. John in a week.
The scene on St. John is more appropriate for a 5 yr old, IMHO, than a lot of the BVI. But if you are set on the BVI and sailing out of Road Town, you might take a mooring in the Bight at Norman Island and enjoy the beach by the restaurant. Moving east, you might consider Great Harbour on Peter Island, but your next stop might be Virgin Gorda. With a young child, you might consider taking a slip at the Yacht Harbor at Spanish Town and taking a taxi to the Baths, which would be the highlight of your trip. Another stop might be Marina Cay, which also has a family-friendly Pusser's restaurant and a kid-friendly beach, but the water isn't the cleanest here. Working your way around Tortola, another stop might be Jost van Dyke. You could pick up a mooring in Great Harbour and take a taxi to White Bay, where you could get a pain killer at the Soggy Dollar Bar and enjoy their beach. The 4-course dinner at the attached Sand Castle hotel is another winner. You could check out Foxy's at Great Harbour, where you can get a meal, but it's more of an adult scene in the evening. Given your interest in gentle sailing, you need to be aware that moving in an easterly direction on either side of Tortola is going to be a slog to weather. If it's very windy you might consider motoring if you need to go any distance in this direction.